The 100 Greatest Movies of the Nineties

Ah, the 1990s – the decade that brought you indie-cinema breakouts and bullet-time blockbusters, fight clubs and foul-mouthed clerks, charismatic cannibal serial killers and “Choose Life!” sloganeering, Rushmore Academy overachievers and Royales with Cheese. Looking back on the movies that made the Nineties such a surprisingly fertile period for filmmakers and film lovers, you can see how so much of the foundation for the past few decades was laid so early on, from the rise of documentaries as a mainstream phenomena to the meta touches that would turn so many mix-and-match movies into wax museums with pulses. Sundance was to independent auteurs as Seattle was to grunge rockers. We would hang with slackers and Scottish junkies, smooth-talking criminals and abiding dudes. We would get cyberpunk as fuck. We would know kung fu – whoa!

So we’ve assembled a crack team of film fanatics, culture vultures, pop-culture pundits and various critics to weigh in on the 100 greatest movies of the Nineties. From Oscar-winners to obscure-but-wonderful gems, nonfiction social-issue sagas to a seven-hour Hungarian masterpiece, Titanic to Tarantino, these are the films we still argue over, quote endlessly and return to again and again. Crank up your dial-up connection, crack open a Sub Zero and let the arguments begin.

100. ‘Romeo + Juliet’ (1996)

Shakespeare had a hell of a run in the Nineties, from the riot grrrl shrew-taming of Ten Things I Hate About You to Keanu as Prince Hal in My Own Private Idaho. But Baz Luhrmann really did the Bard proud with his MTV take on the tale of star-crossed lovers, snagging two of the era’s glossiest newcomers: Claire Danes, fresh from My So-Called Life; and a baby-faced, soon-to-be-superstar Leonardo DiCaprio. It’s the play reimagined as a pulp fantasy, complete with guns, drugs, swimming pools, SoCal gang warfare (let’s rumble at Verona Beach!), angel wings, doe-eyed glances through fish tanks and a soundtrack that’s as iconic as the film itself. RS

99. ‘Clerks’ (1994)

Shot in grainy black and white and loosely based on director Kevin Smith’s life at the time, this no-budget film follows a convenience store clerk (Brian O’Halloran), and his video-store-clerk best friend (Jeff Anderson) over the course of a single day. Clerks captures both the banality of service work and a sort of dirtbag-vérité weirdness that would end up becoming a go-to template for Nineties indie movies; just for kicks, he throws in a stoner duo (hello, Jay and Silent Bob!) that would end up becoming the cornerstone of the Smithverse. Between its foul-mouthed running commentary on everything from Star Wars to dicks and its dead-on sense of grungy ennui, Smith’s D.I.Y. debut captures a certain post-Slacker cultural moment and traps it in amber. AB

98. ‘Buffalo ’66’ (1998)

A neurotic recent parolee (writer-director Vincent Gallo) abducts a dancer (Christina Ricci), forcing her to meet his parents, played with batshit majesty by Ben Gazzara and Anjelica Huston. She goes along with the act, pretending to be his loving girlfriend – she’s the only one who sees right through his psycho surface to the wounded little boy inside. One of the funniest movies about male insecurity ever made, Gallo’s amour fou story becomes a breathless appreciation of upstate New York dreariness, the lunatic majesty of its creator and the idea that love means always having to say you’re sorry. And that delirious donut-shop declaration ending is a keeper. SB

97. ‘The Ice Storm’ (1997)

The subgenre of movies in which wealthy suburban parents watch their own failings magnified in their children was a crowded one in the 1990s – so kudos to Ang Lee for handling the adaptation of Rick Moody’s book with uncommon delicacy and insight. A Connecticut family, led by a philandering Kevin Kline and a brittle, embittered Joan Allen, try to make it through Thanksgiving ’73 alive, as their kids begin to wise up, the sexual revolution begins to cause collateral damage and the country begins to slouch in to the age of Watergate. The tragedy at the end feels sincerely mournful – like an elegy for the end of innocence in America. BT

96. ‘The Virgin Suicides’ (1999)

Want to survive adolescence – or, better yet, adulthood? Then watch this playful, tragic memento mori about the Lisbon sisters, a quintet of Michigan teens in the 1970s who cast a spell on their small town after the youngest impales herself on a fence. She will eventually inspire her siblings to similar fates. It’s the neighbourhood boys who really suffer, however, fetishising what was left behind (postcards, travel magazines, diary entries) and aching for memory to become insight. Sofia Coppola’s intoxicating debut feature, based on the novel by Jeffrey Eugenides, launched her singular career of films about yearning characters imprisoned by their circumstances. SG

95. ‘Orlando’ (1992)

This adaptation of Virginia Woolf’s novel about an apparently immortal Elizabethan-era nobleman who is transformed, midway through his long life, into a woman provided the perfect early showcase for Tilda Swinton’s otherworldly charisma. A poet whose romantic spirit propels him, then her, through the centuries, Swinton’s Orlando doesn’t pass as a man in the film’s first half so much as transcend gender from beginning to end. Director Sally Potter complements the career-making performance by housing it in a peerless, creative free-for-all meditation on masculinity, femininity and time. JB

94. ‘Singles’ (1992)

Before a bunch of New Yorkers sipping coffee at Central Perk made the love lives of Generation X-ers must-see-TV, Cameron Crowe’s ensemble rom-com captured twentysomething dating in a pre-Tinder, post-Nevermind world. Campbell Scott and Kyra Sedgwick are the adults in the room while Matt Dillon’s naïve Jim Morrison-in-flannel frontman became both a perfect symbol and a simultaneous parody of Pacific Northwestern slackerdom; this was the movie that launched a million Bridget Fonda crushes. It also masterfully documented the decade’s most enduring music movement: Armed with an instant classic soundtrack featuring Pearl Jam, Alice in Chains and Soundgarden, plus solo cuts from the late Chris Cornell, the movie doubles nicely as a subcultural time capsule – The Decline of Western Civilization of the grunge scene. DK

93. ‘Billy Madison’ (1995)

Before the cinema du Adam Sandler meant nothing but bro baiting and phone-it-in paydays, the ex-SNL star gave us this masterclass in manchild comedy – a genuinely weird, warped story of a spoiled rich doofus who, in order to stay spoiled and rich, must do the impossible. a.k.a. repeat kindergarten through high school in record time. This is Sandler in all his unhinged abbie-doobie glory, fighting off 3-metre-tall penguins and staging elaborate musical numbers that end with operatic pleas for gum; he’d never be this over-the-top odd or out-and-out hilarious again. And it features the greatest academic competition to ever end with the words, “I award you no points, and may God have mercy on your soul.” DF

92. ‘The Usual Suspects’ (1995)

“The greatest trick the devil ever pulled was convincing the world that he didn’t exist.” So says slippery Verbal Kint to a short-tempered cop (Chazz Palminteri) during the tense interrogation that forms the spine of Bryan Singer’s unforgettable second feature. Kevin Spacey won his first Oscar for his turn as the runt of a criminal quintet roped into pulling a doomed heist on behalf of a bad-guy bogeyman – the mysterious, legendary Keyzer Söze. But the film is stacked with top-notch character actors doing exemplary work, including Gabriel Byrne, Benicio Del Toro, Pete Postlethwaite and Giancarlo Esposito among them. And its twist ending still packs a wallop. GM

91. ‘Lone Star’ (1996)

“Forget the Alamo”: That’s not just the final line of writer-director John Sayles’ best film but also a tidy summation of how history weighs people down. Chris Cooper plays a soft-spoken Texas sheriff investigating a decades-old murder, which forces him to confront the legacy of his father (Matthew McConaughey), the community’s beloved former lawman-in-chief. Seamlessly interweaving flashbacks and the present, Sayles’ evocation about the past never really being the past was a highlight of Nineties American independent cinema – smart, sober, novelistic and politically astute. TGr

90. ‘Dumb and Dumber’ (1994)

Masterful physical comedic performances by burgeoning movie star Jim Carrey and a straw-haired Jeff Daniels punctuate Bobby and Peter Farrelly’s endlessly quotable raunch-com classic, about two idiot friends who take a cross-country road trip in a dog-shaped truck to return a briefcase of money. Its a highpoint in Nineties lowbrow comedy, one whose ex-lax pranks, blue and orange tuxedos, urine-filled bottles of beer and annoying “Mockingbird” singing-a-longs by the movie’s dumb-ass double act are still referenced by millions of fans. The reason why is simple. It’s because we like them. We like them a lot. AS

89. ‘The Long Day Closes’ (1992)

An 11-year old named Bud (Leigh McCormack) comes of age in postwar Liverpool, moving between home, school, church and the movies – all wondrously linked in an extended bird’s-eye tracking sequence scored to Debbie Reynolds’ “Tammy.” Overflowing with song, sentiment and elegant compositions, this autobiographical marvel from Terence Davies, England’s maestro of conflicted nostalgia, mines the past for both burnished beauty and unshakable trauma. EH

88. ‘Casino’ (1995)

The rise and fall of the gangsters who turned Vegas into a violent, mobbed-up money-making machine, with both Louis Prima and loud rock & roll on the soundtrack – could this Martin Scorsese epic sound any more Martin Scorsese-ier? Like Goodfellas with glitz, the director’s look at an empire built on crime and paranoia employs a lot of his signature elements – it’s like a one-stop Marty shopping spot, complete with an angry Robert De Niro, La Cosa Nostra, Rolling Stones tunes, a Nicholas Pileggi script, incredible Steadicam set pieces and a brutal Joe Pesci death sequence. Plus you get a Golden Globe-winning Sharon Stone as a femme fatale who destroys a “good thing” in the desert and nearly brings down Sin City in the aftermath. DK

87. ‘Velvet Goldmine’ (1998)

Right from the opening credits scene, featuring a group of colourfully dressed glam rock British kids running down the street to Brian Eno’s “Needles in the Camel’s Eye,” Todd Haynes’ ode to Seventies glam virtually screams with glee. Told Citizen Kane-style as a journalist (Christian Bale) tries to track down a Bowiesque figure named Brian Slade (Jonathan Rhys-Meyers) years after his chart-topping heyday, the movie stews in the glitter and mythology that characterised a bygone era of rock history and reclaims it for the modern New Queer Cinema era. KYK

86. ‘A Brighter Summer Day’ (1991)

Taiwanese director Edward Yang’s long, sprawling history lesson tells two parallel stories: the first chronicles warring youth street gangs in 1960’s Taipei; and the second follows a family struggling to maintain their modest lifestyle under uneasy circumstances. In the centre lies a young rebel (Chang Chen) who falls for a gang leader’s girlfriend, with tragic results. This expansive, intimate period epic filters a universal tale of adolescence through an unstable political environment, creating a work both bound to its cultural context and completely stuck out of time. VM

85. ‘Titanic’ (1997)

A flower-child, a macho fetishist, a tech nerd – James Cameron can be all these things at once. And with this tragic romance set aboard the doomed, iceberg-bound ocean liner, he proved he could speak fluent teenager as well. Yes, Titanic‘s amazing effects and impressively choreographed scenes of chaos recreate the sinking ship going down with FX-heavy fidelity. But an entire generation of moviegoers still embrace this megablockbuster because Cameron crafted an earnest, swooning romance between two kids, and in Leonardo DiCaprio and Kate Winslet, he found two ideal actors – perched between teen stardom and adulthood, able to convey both free-spirited puppy love and genuine depth and despair. Come for the awe-inspiring spectacle; stay for the breathtaking moments of tenderness. BE

84. ‘Swingers’ (1996)

Actor Jon Favreau’s writing debut is a sharp, witty meditation on feeling like a loser. A down-on-his-luck wannabe movie actor (Favreau) is stuck on the girlfriend who dumped him when he left New York City for L.A. His fast-talking friends – played by Ron Livingston and Vince Vaughn in his breakout role – try to cheer him up with a trip to Las Vegas and endless hipster-bro hang-outs. Nothing seems to work. Then he meets a woman (Heather Graham) who likes swing dancing. The film’s off-the-cuff D.I.Y. sensibility, unique dialogue (“Look at all the beautiful babies here,” “I’m a Dorothy”) and hilarious dynamic between sad-sack Favreau and fun-loving Vaughn made it a Nineties touchstone. It was so money and it didn’t even know it. KG

83. ‘Last Night’ (1998)

Welcome to the most Canadian apocalypse ever envisioned. The world is ending at midnight, as a result of some mysterious environmental catastrophe. Some people pray, some party, some riot in the streets. But most are painfully polite – the manager of Toronto’s gas company spends his final hours calling customers at home to assure them the power will stay on. (How much more Canadian could it get? He’s played by David Cronenberg.) It’s a heart-piercing gem from writer/director Don McKellar (of the cult sitcom Twitch City), who – along with a then-unknown Sandra Oh, Sarah Polley and Genevieve Bujold – spends his last hours searching for some kind of human connection before it’s too late. RS

82. ‘Raise the Red Lantern’ (1991)

The major breakthrough work of China’s “Fifth Generation” filmmaking wave, Zhang Yimou’s colourful, caustic tale follows a young woman (a breathtaking Gong Li) who’d rather become a rich man’s courtesan than a poor man’s spouse – and comes to realise that a gorgeous gilded cage is still a prison. Also, when you’ve taken the position of “fourth wife,” you’re likely to incur the wrath of your fellow mistresses fighting for scraps. A damning tale of a smart woman slowly suffocating under social constraints, and proof that Zhang and his star were one of the decade’s greatest director/actress combos – a mainland Von Sternberg and Dietrich for the modern age. SB

81. ‘Election’ (1999)

Pick Flick! Reese Witherspoon’s obnoxiously plucky Tracy Flick is determined to win the election for student council president at her Omaha high school. Matthew Broderick is the civics teacher who decides to stand in her way, convincing a popular jock (Chris Klein) to run an opposing campaign. Illicit affairs, political treachery and one very uncomfortable looking bee-sting helped make Alexander Payne’s brilliant black comedy a critical hit. His gleefully subversive script, written with longtime collaborator Jim Taylor and adapted from Tom Perrotta’s novel, earned an Oscar nomination. Any resemblance between the characters here and real-life politicians are, of course, completely coincidental. GM

80. ‘Fear and Loathing in Las Vegas’ (1998)

Only Terry Gilliam could mount such a chaotic and kaleidoscopic adaptation of Hunter S. Thompson’s gonzo dispatch – a mescaline-penned eulogy for the Summer of Love and an eerie premonition of the Watergate era. Johnny Depp completely embodies the late, great journalist as his “Raoul Duke” teeters along the Las Vegas Strip and inhales an ether-soaked American flag, with Benicio Del Toro’s unhinged lawyer playing the buzzing Bonnie to our tour guide’s acid-fried Clyde. The film’s bizarre epilogue: Seven years after its release, Depp helped fire Thompson’s ashes out of a cannon at the writer’s funeral. DK

79. ‘Bad Lieutenant’ (1992)

A relentless odyssey of a New York City detective on a violent, drug-fuelled downward spiral, Abel Ferrara’s free-form descent into the depths follows the sort of law-enforcement antihero who isn’t above swiping dope from a murder scene or publicly masturbating during a routine traffic stop. So far, so Ferrara – and then this scuzzfest begins to reveal itself as a stations-of-the-cross spiritual inquiry, at which point the surreal episodes emanating from the Lieutenant’s pickled mind suddenly take on a serious gravitas. Aided and abetted by Harvey Keitel’s gone-nuclear performance (that howling Man v. Christ vignette!), the director’s take-no-prisoner’s tale of redemption is one of the most religious movies of the decades – a perfect melding of the poetic and the profane, the agony and the ecstasy. SB

78. ‘The Shawshank Redemption’ (1994)

“Get busy living, or get busy dying,” notes jailbird Andy Dufresne (Tim Robbins) in Frank Darabont’s prison drama about a wrongfully convicted banker navigating the harsh realities of life in the joint, and the friends and foes he meets along the way. Narrated with a novelist’s wit by Morgan Freeman’s Red, and featuring the justly famous shots Robbins stripping a shit-stained denim shirt off in the pouring rain – Shawshank is a tale of triumph and tragedy, crime and punishment. There’s a reason it’s been on or near the top of IMDB’s most-popular-movies rankings for ages. AS

77. ‘Terminator 2: Judgment Day’ (1991)

It’s not the T-1000 that makes James Cameron’s sequel better than his brilliant 1984 B-movie original –– although an indefatigable orb that can melt, shatter and reconstitute itself is a lot more menacing than today’s supervillains. No, the glory belongs to the film’s ripped-up in-house Wonder Woman: The director’s then-wife Linda Hamilton, reprising her role as a fierce Madonna who must protect her saviour-in-the-making son (Edward Furlong). Young John Connor’s bond with Arnold Schwarzenegger’s increasingly sentient, former killing machine is touching, and the violence is deftly orchestrated. But Hamilton’s muscular transformation and badass military bearing is what really gives shape to this ultimate showdown between creation and destruction. It’s comforting to believe that tough mothers can help prevent the apocalypse – then and now. PR

76. ‘The Age of Innocence’ (1993)

Overshadowed by fellow period dramas Schindler’s List, The Remains of the Day and The Piano, Martin Scorsese’s adaptation of Edith Wharton’s gutting novel about 19th century New York now seems like a Hollywood miracle. Thanks to its elaborate, anal-retentive interiors and costumes, the film comes on like a tasteful frock drama, but underneath those corsets and bowler caps are piranhas at their most vicious and unsparing. Daniel Day-Lewis and Michelle Pfeiffer play people whose mutual simmering passions are no match for societal rules and decorum, putting the lie to notions of American liberalism and upward mobility. It’s a movie that will inspire violent crying jags from even the manliest of Goodfellas fans. EH

75. ‘There’s Something About Mary’ (1998)

Let us praise Cameron Diaz, who’s career-defining role in Bobby and Peter Farrelly’s hit comedy is ridiculously flawless: a rail-thin, goofy-grinned, beer-chugging orthopaedic surgeon with a yen for SportsCenter. Yet the brothers brilliantly subvert that idolatry with a farce about maniacal male desire, as Ben Stiller’s sweet-natured suitor, smitten since high school, soon faces a widening circle of testosterone-fuelled obsession. But what’s really remarkable is the film’s joyous profanity, be it Stiller’s zippered genitalia (a five-minute reverie), Diaz’s semen-stiffened bangs or an electrocuted border terrier. There’s a huge heart behind the shenanigans, making this lark the missing link between Zucker-Abrahams-Zucker’s Airplane!/Naked Gun antics and Judd Apatow’s humane hilarity. SG

74. ‘The City of Lost Children’ (1995)

French directors Jean-Pierre Jeunet and Marc Caro build on the demented irreverence of their debut Delicatessen with this visually audacious sci-fi fantasy about a mad (in every sense of the word) scientist who, unable to dream himself, kidnaps nearby orphans and attempts to rob them of their REM cycles. Rubber-faced clones, talking brains and a distinct green mist all add fractured fairy-tale elements, while Ron Perlman (who, according to Jeunet, fired his agent for not showing him the script) brings the pathos as the film’s in-house gentle giant. JN

73. ‘Schindler’s List’ (1993)

It may be sandwiched between Jurassic Park movies – but Steven Spielberg’s Oscar-winning Holocaust drama signalled a new phase in his career, with the blockbuster maestro opening up to far more austere considerations. (You do not get Munich or Lincoln without it.) Shot in a black-and-white that’s as wondrously decadent as often as it’s stark and newsreel-like, it’s a film about flawed and revealingly human men, starting with Oskar Schindler (Liam Neeson), a war profiteer who efforts to shelter the Jews in his factory are accidental before they turn deliberate. Through his awakened conscience, Spielberg’s film will forever provoke our own. ST

72. ‘Before Sunrise’ (1995)

One of the movies’ greatest meet-cutes, Richard Linklater’s walking-and-talking travelogue follows two strangers – an an American boy (Ethan Hawke) and a French girl (Julie Delpy) – who impulsively spend an evening wandering around Vienna together. Flirtations and awkward first-date interactions share screen time with getting-to-know-you type games and typical self-aware twentysomething commentary on their own rose-tinted romanticism. It doesn’t have a happy ending so much as a “will they or won’t they?” fade-out – a question which would get answered as Linklater fashioned the story into a trilogy. The first time, however, is still a singular charm. KYK

71. ‘Edward Scissorhands’ (1990)

Tim Burton’s skewed tale on a latex-clad misfit with shears for hands (Johnny Depp at his moist-eyed Gothiest) is more than just a Frankenstein riff set in cartoonish suburbia; it’s also his most personal film to date, a sensitive tribute to social outcasts, artistic outliers and anyone who’s ever felt like the world doesn’t get them at all. Even when the director is paying homage to influences ranging from Hammer horror movies to Disney fairy tales, the movie never feels like a sum of its stitched-together parts or an ironic put-on. What started as a sketch from the margins of the filmmaker’s notebooks is now an iconic symbol of isolation – the man who truly hurts everything he loves. BT

70. ‘When We Were Kings’ (1996)

If he hadn’t been the century’s most compelling athlete, Muhammad Ali could have had a career in pictures. This Oscar-winning documentary about the champ’s legendary “Rumble in the Jungle” bout with George Foreman in Zaire covers many topics: our fascination with boxing, the preparations that went into the fight, America’s political and racial divide. But rising above it all is Ali, who (at age 32) was considered a has-been destined to be destroyed by the younger, fiercer Foreman. Director Leon Gast lets the boxer take centre stage, and the archival footage remains remarkable: Here is a fighter who had already taken on the U.S. government by refusing to enlist in the Vietnam War, now staring down the possibility of retirement, as well as an opponent determined to slay him. Fictional sports movies are rarely this powerful and inspiring. TGr

69. ‘La Belle Noiseuse’ (1991)

The late,great French New Wave auteur Jean Rivette hit an autumnal peak with this elegiac meditation on pain and creativity. It’s nearly four hours of Emmanuelle Beart naked – and that’s not even the most audacious thing about it. Michael Piccoli is an ageing painter who put down his brush years ago, abandoning his unfinished opus, “The Beautiful Nuisance.” But Beart goads him into starting again, with her as his model. Long stretches of the film are just the two of them at work, as he paints over his past, stroke by stroke – a mediation on the creative process and emotional turmoil that goes with it for both artist and muse. (And wife Jane Birkin.) He aspires to “blood on the canvas” – which is exactly what Rivette achieved. RS

68. ‘Friday’ (1995)

Ice Cube and co-writer DJ Pooh hoped to make what the rapper has called a “hood classic” in the vein of Car Wash or Cheech and Chong’s movies – instead, their stoner comedy, made for an estimated $3.5 million, transcended their expectations, pulling in some $28 million at the box office and became a bona fide cult favourite. Down-on-his-luck Craig (Ice Cube) gets fired on his day off; he and his loquacious pothead friend Smokey (Chris Tucker) then have to beg, borrow or steal $200 to pay off a frightening drug dealer. The film spawned two memes (“You got knocked the fuck out!” and the enduring “Bye Felicia”) and solidified the former N.W.A growler and the future Rush Hour star as box-office draws into the next decade. KG

67. ‘Life Is Sweet’ (1990)

Mike Leigh’s breakthrough feature expounds on that notion about every unhappy family being unhappy in its own way … as well as being joyous, angry, sorrowful and completely fucked up in equally singular fashions. The more time you spend with the movie’s clan – the culinary paterfamilias (Jim Broadbent), the ray-of-light mom (Alison Steadman), the raging, bulimic Nicola (a pre-Absolutely Fabulous Jane Horrocks) and her butch twin sister Natalie (Claire Skinner) – the more Leigh & co. let you see how, in good times and bad, the bond between them runs deeper than blood. Throw in Timothy Spall’s amateur restaurateur and ladies’ man Aubrey, arguably the funniest character in the director’s back catalog, and you have a 360-degree heartfelt, humanistic portrait of Britain’s lower-middle-class. There’s as much bitterness as there is sweetness. But you never think the title is ironic for a single second. DF

66. ‘Madonna: Truth or Dare’ (1991)

Madonna did loads of acting in the Nineties, even picking up an English accent somewhere along the way. But as this documentary proved, the character she was born to play was Madonna. Truth or Dare is Peak Ciccone, raging on her 1990 Blond Ambition tour, terrorising her entourage of dancers and back-up singers. It’s a pre-reality-TV time capsule of a moment when Madge was the only pop star who mattered – as she says, “I’m interested in pushing people’s buttons, being provocative and political.” (The scene where her dancers attend an ACT UP rally was the first time most Americans got to hear a “we’re here, we’re queer, get used to it” chant.) When the Toronto police threaten to arrest her if she masturbates onstage during “Like a Virgin,” she asks how the cops define masturbation: “When you stick your hand in your crotch.” Spoiler: She sticks her hand in her crotch. RS

65. ‘Satantango’ (1994)

Set over a miserable two-day period (and sometimes feeling just as long in the viewing), Béla Tarr’s grimy, spectacularly immersive seven-hour odyssey is the Nineties landmark that all serious film fans must reckon with. Commit an afternoon to this Hungarian-made epic and your mind will be rebooted: Hypnotic shots span an uninterrupted eight minutes or more, composer Mihály Víg’s seesawing accordion score creates a dark carnival in your head and crisp black-and-white imagery brings on a waking Lynchian nightmare. The material itself isn’t easy, concerning (but not limited to) power grabs in a depressed farming community, the oblique spectre of fascism and one extremely unlucky cat. But the takeaway is nothing less than profound: the whole of cinema reinvented. JR

64. ‘Wayne’s World’ (1992)

Still the most successful film adaptation of a Saturday Night Live sketch to date, Mike Myers and Dana Carvey’s most excellent feature-length romp brings their titular public-access goofballs to the big screen, complete with a sleazy corporate producer (Rob Lowe), a gleeful skewering of product placement and a “choose your own adventure” style ending. It’s endlessly quotable (“Babe-raham Lincoln,” “That’s what she said!” and the gloriously onomatopoetic “Schwing!”) and a peerless example of how to combine headbanging dude-ness with genuine sweetness, one “Bohemian Rhapsody” sing-along at a time. Party on. AB

63. ‘Jackie Brown’ (1997)

The early rap on Quentin Tarantino was that he was merely the sum of his pop culture influences – then right when everyone was expecting Pulp Fiction II, he dropped this rich adaptation of Elmore Leonard’s crime novel and proved that cinematic obsessions and insight into human nature weren’t mutually exclusive. The story of an ageing stewardess (Pam Grier) caught up with a rat-tail–sporting gangster (Samuel L. Jackson) and some stoic-to-stoned unsavoury types has his typical rat-a-tat dialogue, soundtrack deep-cuts, dynamic set pieces and meta-references. But it also has a surprisingly sincere middle-aged romance between its lead character and Robert Forster’s bail bondsman – it’s still his most “mature” movie to date – and his blushing fascination with blaxploitation icon Grier doubles as a tribute the soulful black culture of his youth. SB

62. ‘Audition’ (1999)

A widowed TV producer dives back into the dating pool with the help of his devious pal, who sets up an audition purely for the purpose of attracting eligible women. The scam works. Our hero falls for a shy, pretty loner half his age. It sounds like the plot of a dopey rom-com, and director Takashi Miike, Japan’s reigning master of all things gory and twisted, takes nearly 45 minutes to drop his first hint that this is actually a horror movie. But he only needs one shot to shatter the banal original premise and transform the film into a gruesome, indelible allegory for the pain men unthinkingly inflict on women. You’ll know it when you see it. Then all hell breaks loose. Good luck. JB

61. ‘Clueless’ (1995)

Speak the truth, Alicia Silverstone: “Searching for a boy in high school is like looking for meaning in a Pauly Shore movie.” Over a decade after directing the Eighties’ finest teen comedy (Fast Times at Ridgemont High), Amy Heckerling did the same favour for the Nineties, with one deliriously quotable barb after another – from “going postal” to “surfing the crimson wave.” Silverstone, everybody’s favourite Aerosmith video vixen, stars as aspiring fashion plate Cher Horowitz, shopping her way through an L.A. full of Baldwins, Bettys, Monets and virgins who can’t drive. The late great Brittany Murphy shines as the Mentos-loving skater girl. (You’re rolling with the homies in our hearts, Brit.) And Cher’s thoughts on immigration are timelier than ever in 2017 – it still does “not” say RSVP on the Statue of Liberty. As if! RS

60. ‘Natural Born Killers’ (1994)

Director Oliver Stone was no stranger to controversy when he set out to helm the phantasmagorical, media-fried story of serial-killer celebrity couple Mickey and Mallory Knox, played by Woody Harrelson and Juliette Lewis in career-peak performances. Alleged copycat killings and lawsuits (including one brought by author John Grisham) ensued. But the director’s ruthless satire of American infotainment bloodlust – embodied by Robert Downey Jr.’s sleazeball tabloid-TV host Wayne Gale, his pre–Iron Man peak – stands the test of time. So, for that matter, does the film’s hyperkinetic editing, surrealist imagery and Trent Reznor–curated soundtrack. It’s incredibly Nineties, right down to the original story by Quentin Tarantino. STC

59. ‘Being John Malkovich’ (1999)

A marionette-obsessed office schlub (John Cusack) finds a gateway into the brain of the titular Oscar-winning actor; soon, the celebrity’s cranium becomes home to a battle royale between the puppeteer, his wife (Cameron Diaz) and a coworker (Catherine Keener). Perhaps the strangest movie to ever receive Oscar love – and the only one that features wormholes that exit on the New Jersey Turnpike, bizarre love triangles and Charlie Sheen playing a future version of himself – the feature debut of music-video visionary Spike Jonze remains a mini meta-masterpiece. It was also an introduction into the mind of avant-screenwriter Charlie Kaufman, who quickly established himself as one of Hollywood’s most unique voices. DK

58. ‘Scream’ (1996)

“What’s your favourite scary movie?” This meta-horror hit turned a simple question into an almost existential quandary, thanks to A Nightmare on Elm Street mastermind Wes Craven and a self-aware script that toyed with horror clichés (e.g., “if you have sex, you’ll probably die”) by future Dawson’s Creek creator Kevin Williamson. Neve Campbell and a cadre of no-goodnik teens attempt to unmask the chatty, horror-movie–obsessed serial killer who’s been offing them, with little help from the nosy newscaster (Courtney Cox) and fumbling cop (David Arquette). It inspired three sequels, a MTV series and the successful Scary Movie parody franchise, and its snarky sense of irony inspired countless stylistic rip-offs that paled when compared to the original and its Ghostface killer. KG

57. ‘Dazed and Confused’ (1993)

Director Richard Linklater considers this follow-up to Slacker an exorcism of painful high school memories – the scores of stoners and nostalgists who have worn out VHS and/or DVD copies of this teen-movie gem, however, clearly feel otherwise. The rituals and keggers of the last day of school circa 1976 are so vividly recreated that the film almost doubles as a time machine, immersing you in the fashion, music and pot-fueled meanderings of another era. But the perfect evocation of the confusion and freedom of youth, however, feels timeless. It’s also a prescient casting call for the next generation of stars, including Parker Posey as an alpha mean girl, Ben Affleck as a hilariously apoplectic fifth-year senior and Matthew McConaughey as a skeevy twentysomething with an interest in high school girls. Alright, alright, alright. ST

56. ‘Seven’ (1995)

In this heir apparent to The Silence of the Lambs, David Fincher masterfully recalibrates the noir genre for a nihilistic tale of Biblical vengeance. The sun literally never shines on Brad Pitt and Morgan Freeman’s odd-couple detectives as they hunt down a grimly imaginative serial killer (an unnerving Kevin Spacey). This tense, unrelenting and expertly paced thriller was an early indication of the director’s massive talent, and add “being the first to discover the violent poetry of Gwyneth Paltrow’s head” to the list of Fincher’s many accomplishments (see also: Steven Soderbergh’s Contagion). What’s in the box indeed. PR

55. ‘Babe: Pig in the City’ (1998)

The original Babe remains a staple of anthropomorphic-animals kid’s cinema, but the tale of a pig who finds love and acceptance among sheepdogs took a much weirder, stranger turn in this sequel, directed by, of all people, Mad Max mastermind George Miller. This follow-up transports the titular piglet to a hotel full of beasties in a fantastical, Dickensian metropolis; a pit bull nearly drowns in a hallucinatory, Lynch-esque scene and an elderly Mickey Rooney plays a sinister clown. Pig in the City didn’t just build upon its predecessor; it reinvented it, and wasn’t afraid to wrap its sweetness in a darkly stylish wrapper. JS

54. ‘Paradise Lost: The Child Murders at Robin Hood Hills’ (1996)

The story of three teenagers’ convictions and subsequent legal battles over the murders of three children in West Memphis, Arkansas led to one of the decade’s most engrossing and enraging crime documentaries. Filmmakers Joe Berlinger and Bruce Sinofsky (Some Kind of Monster) give all sides – the overzealous prosecutor, the bewildered defendants, the thirst-for-blood community – a platform to vent their opinions on the controversial case. But as the film progresses and doubt about the teenagers’ guilt builds up, the duo peels the layers back on a small town desperate for a villain. Thanks to the movie and it subsequent follow-ups, the case would become a pop culture rallying cry, with Eddie Vedder, Johnny Depp and Metallica, among many others, championing the trio’s release. You couldn’t ask for a better example of deep-dive docu-journalism. JN

53. ‘Wild at Heart’ (1990)

Somehow in the midst of creating one of the most influential TV series ever, David Lynch banged out this transcendent romance – a Wizard of Oz-influenced take on Barry Gifford’s novel about two sexed-up lovers and the weird-Americana, nightmarish world of trouble that their relationship unleashes. Nicolas Cage’s magnetic, Elvis-obsessed Sailor and Lynch mainstay Laura Dern make the journey hotter than Georgia asphalt, as this warped, wild road movie propels the couple towards a macabre, brutal but (for Lynch, anyway) uncharacteristically optimistic fate. TGi

52. ‘Metropolitan’ (1990)

Indie writer-director Whit Stillman may be the movies’ most eloquent (and low-key hilarious) bard of the vagaries of the American upper classes. He came out martini glass swinging with his first film, about a middle-class Princeton kid (Edward Clements) who stumbles his way into a circle of wealthy young Manhattanites during debutante ball season. With enough witty bon mots to fill a Noël Coward play, Metropolitan is both a cutting takedown of the 1-percent and a loving ode to its quirks. Bridging the divide between the Eighties and Nineties, this was probably also one of the last movies where you’ll find a pack of teenagers unironically rocking tuxes and ball gowns for a night on the town. JS

51. ‘South Park: Bigger, Longer, Uncut’ (1999)

Think back to when a big screen version of the low-rent animated cable comedy series sounded misguided. Also, it was going to be a musical. And then you sat in a multiplex and watched Saddam Hussein get buggered by Satan (a behooved, emotionally well-adjusted Beelzebub at that). Trey Parker and Matt Stone not only took their small-screen hit to the big screen without embarrassing themselves, they created a goofy, giddy portrait of a war-crazed America that you could tap your toes to. Every crazy profane idea suddenly seemingly permissible – so were decidedly non-anarchic endeavours like songcraft and sincerity. The duo pissed on our heads and called it art. And it was. EH

50. ‘L.A. Confidential’ (1997)

Russell Crowe and Guy Pearce weren’t yet stars when they played two mismatched police detectives – one raging, one shrewd – uncovering corruption in 1950s Los Angeles. Both actors light up the screen, even when set against an ice-cool Kevin Spacey (as a vice cop who specialises in showbiz) and an Oscar-wining Kim Basinger (as a high-priced prostitute with mob ties). Director Curtis Hanson and screenwriter Brian Helgeland turn James Ellroy’s literary pulp novel into a sweeping, sophisticated urban crime epic – so cracklingly entertaining and thematically rich that it felt like a long-lost Hollywood classic even in 1997. NM

49. ‘Heavenly Creatures’ (1994)

Before Peter Jackson took us all to Middle-earth, he brought moviegoers to the mad world of two troubled teenagers – a fictional universe every bit as engrossing as J.R.R. Tolkien’s, but far more romantic and lethal. Based on a true-crime story, the film depicts pre-stardom Kate Winslet and Melanie Lynskey as Pauline Parker and Juliet Hume, two New Zealand teenagers whose BFF-ship blossoms first into love, then madness and ultimately murder. Jackson’s kinetic camera captures the rapturous swirl of teenage dreams before plunging us into its brutal, bloody endpoint. It’s a beautiful dark twisted fantasy. STC

48. ‘Poison’ (1991)

Todd Haynes’ lo-fi triptych heralded more than just a vital new talent – it helped spark the New Queer Cinema movement, pissed off right-wing N.E.A. haters, further established Sundance as ground zero for American indie visionaries and almost singlehandedly introduced subversive-lit godhead Jean Genet to a new generation. “Hero,” uses a found-footage faux-doc format to profile a kid, a crime and an unexplained occurrence; “Homo” takes Genet’s Our Lady of the Flowers scenario of lovestruck prisoners and turns it into a rough-trade Pierre et Gilles portfolio; and “Horror” apes Fifties monster flicks to craft a story about a mysterious new disease. The shadow of AIDS hovers heavily over its tales – but so does a sense of liberation and the idea that there were still taboo subjects left to drag out into the light. DF 

47. ‘To Sleep With Anger’ (1990)

Everybody knows a guy like Harry (Danny Glover, who should have won an Oscar for this), who simultaneously brings the party and ruins it. He happens to be in town to visit old friends, ex-Southerners transplanted to Los Angeles during the Second Great Migration – and to clean out a closet full of skeletons from their Jim Crow past. Writer-director Charles Burnett (Killer of Sheep) crafted a prismatic folk tale where every line is a subtle threat or tease. A masterful, magic realist black-Black comedy. SB

46. ‘JFK’ (1991)

You can (and should) push back against the since-debunked assertions in Oliver Stone’s dazzling speculative fiction regarding a vast conspiracy behind the murder of President John F. Kennedy. But what remains indisputably true about this electric, frenzied film – highlighted by career-high turn from Kevin Costner as Jim Garrison, the New Orleans prosecutor determined to uncover the truth – is the firebrand filmmaker’s rage at the killing of an American leader and the idealism he represented. The movie’s screaming-truth-to-power fervour felt vital during its moment – and continues to feel more necessary than ever now. TGr

45. ‘Breaking the Waves’ (1996)

Emily Watson earned a deserved Oscar nomination as Bess, a devout Scottish woman who talks to God – in her mind, He chats back – and marries an oafish oil-rigger (Stellan Skarsgård) who becomes paralysed in an accident. Soon, he’s encouraging her to find other lovers and report back about their sexual dalliances. Filmed with handheld cameras that emphasise the rampaging torment at the movie’s centre, this transcendent melodrama tackles gender inequality and the mysteries of faith with unshakeable intensity. And its shocking ending remains cinematic provocateur Lars Von Trier’s nerviest gambit – he rocks the bells and blows your mind. TGr

44. ‘The Double Life of Veronique’ (1991)

Nestled right between the career-defining achievements of his 10-part magnum opus Dekalog and his Three Colours Trilogy, Polish director Krzysztof Kieslowski gifted audiences with this transcendent drama revolving around two vastly different, strangely identical women. Irene Jacob plays an aspiring Eastern European singer named Weronika, who dies onstage during a concert; the actress also shows up as a French woman named Veronique, who finds herself overcome by inexplicable grief at the moment of her doppelganger’s death. With its gorgeous, dreamlike imagery and magical mystery tour of metaphysical connections, the movie casts a spell on you right from the get-go – and offers proof that some feelings are simply easier to evoke than explain.  BT

43. ‘Starship Troopers’ (1997)

Executed with the go-for-broke daredevilry of a man who just made Showgirls, pervy Dutch director Paul Verhoeven’s sci-fi action film is, limb for severed limb, Hollywood’s most subversive war movie. Pro-military patriots and fans of Robert Heinlein’s ultrasquare 1959 novel arrived at the multiplex only to be confronted by a $105-million piss-take, peopled by gorgeous lunkheads (Casper Van Dien and Denise Richards chief among them) and drenched in antifascist irony. Presciently, Verhoeven adopted a screaming advertorial style, peppering the alien bug hunt with “clickable” recruitment ads and xenophobic news blasts. But it’s his film’s backward glance – to Nazi pageantry and a jack-booted Neil Patrick Harris – that makes Starship Troopers so lovably irresponsible. Is it the future or Fox News? Both. JR

42. ‘The Lion King’ (1994)

This fun (and occasionally problematic) Disney film about a lion avenging the death of his father will make you laugh, cry and sing to your heart’s content. The film’s colourful African landscapes, songs by Elton John and Tim Rice and groundbreaking direction – the wildebeest stampede is still one of the best animated sequences of all time – would go on to influence a new generation of cartoon movies and musicals. In the circle of life, good stories move us all. AS

41. ‘Naked’ (1993)

Mike Leigh’s acidic character study of an intelligent, cynical street philosopher touring of London’s seedy underbelly and leaving a path of emotional destruction in his wake is a strong contender for the decade’s angriest cri de couer –  it’s still a complete verbal assault on the senses. David Thewlis provides one of the Nineties’ greatest performances, giving his character a feral intensity as he trudges through a landscape of urban squalor and challenges every former flame, predatory yuppie, sneering hipster and working-class folk he meets. Though bleak and despairing in tone, Naked also features a profound appreciation for life’s small pleasures – biting wit, unlikely companionship and a desire to live even if there’s no light to be found. VM

40. ‘Unforgiven’ (1992)

When it came to making one last Western, Clint Eastwood wasn’t satisfied with filming a simple revenge tale – instead, the director and former Man With No Name pulled out a critique of the genre that propelled him to iconic status. His William Munny is an aging gunfighter pulled out of retirement to kill two cowboys after they disfigure a prostitute. Unfortunately, he receives more than he bargained for when a self-righteous sheriff (Gene Hackman) gets wind of his plans. Blessed with great supporting performances (especially Hackman and Morgan Freeman) and David Webb Peoples’ airtight script, Unforgiven turns what could have been a traditional horse opera into a meditation upon issues of violence and our country’s moral relativism. “Deserve’s got nothin’ to do with it,” Eastwood’s ex-outlaw wearily sighs. Yet only someone who so thoroughly understood how frontier mythology shaped our nation deserved the right to tear it apart. VM

39. ‘Crash’ (1996)

No, not the didactic race-relations drama that stole Brokeback Mountain‘s Best Picture Oscar – we mean the movie about James Spader fucking a vagina-like wound in Rosanna Arquette’s thigh. J. G. Ballard’s cult novel about sexual obsession with sleek cars and high-speed death was a perfect match for body-horror specialist David Cronenberg, who pared the book down to an elegant 62-page screenplay. Channeling his rough-and-ready earlier productions, the Canadian director captured tail-lit night rides on Toronto’s freeways, and coached a committed cast to haunted performances. Even orchestral composer Howard Shore stripped his game down to a wiry all-electric-guitar score, the perfect soundscape for the place where twisted metal meets tortured flesh. JR

38. ‘Fireworks (Hana-Bi)’ (1997)

Japanese superstar “Beat” Takeshi Kitano has always cultivated an offbeat approach to action and crime dramas, but this is something else entirely. He plays a desperate, violent ex-cop dealing with his wife’s terminal disease – the kind of set-up that often lends itself to treacly melodrama or depressing grit. Instead, what emerges is a film that is at once melancholy and light – a lyrical journey in which the sadness of everyday existence coexists with the delicate levity of art, humour and love. And despite the ridiculously tragic narrative, it’s the kind of movie you can return to over and over again – visually gorgeous and genuinely romantic, albeit with moments of near-absurdist violence. BE

37. ‘All About My Mother’ (1999)

An organ-donation counselling nurse in Madrid suffers her teen son’s death and literally gives away his heart before she retreats to Barcelona to find the boy’s father – a transsexual hustler clueless about his paternity. And that’s just the first 20 minutes! We haven’t gotten to the Sapphic actress, her junkie lover or the pregnant nun yet. Welcome to the cruelly ironic, wildly coincidental world of Pedro Almodóvar, where women are mythologically resilient, men are pathologically oblivious and prostitutes play pattycake in the street. This stunning melodrama, a cathartic LGBTQ landmark that nabbed the Oscar for Best Foreign Film, fused the outrageous with a deeply felt empathy – and paved the way for Laverne Cox and Transparent. SG

36. ‘The Blair Witch Project’ (1999)

It’s the found-footage horror movie that launched a thousand paranormal activities, but Daniel Myrick and Eduardo Sanchez’s out-of-nowhere, no-budget blockbuster is so much more than that. A word-of-mouth phenomenon for months even before it hit theatres, this videotaped account of three student filmmakers who fall prey to the very urban legend they’d set out to chronicle hit summer moviegoers like a mack truck, packing theatres with people who had no idea whether they were watching fiction or fact. Long after the shroud of mystery has been lifted off this Rosetta stone of shaky-cam spookiness, its genre-defining technique has yet to be topped. STC

35. ‘The Player’ (1992)

Only a director with such a consistently troubled relationship with Hollywood like Robert Altman could satirise Tinseltown dealmaking so cleverly that it resuscitated his career in the process. A calculating studio executive named Griffin Mill (Tim Robbins) murders a screenwriter while trying to outmanoeuvre his competition, while a slew of celebrity cameos take aim at everything from movie star personalities – including some of their own – to the cutthroat business of show. Alternately languid and merciless, The Player rightfully ensured that Altman would be able to finance his iconoclastic visions for another 15 years – which itself feels like the movie-industry equivalent of getting away with murder. TGi

34. ‘Crumb’ (1994)

In 1995, underground cartoonist Robert Crumb’s work was known mainly to comics connoisseurs and ex-hippies – so consider Terry Zwigoff’s documentary a vital public service, one which encouraged a wider appreciation of a great American artist. But it’s the intimate, revealing interviews with the creator of Zap Comix and his eccentric brothers, however, that separates this from a gajillion other artist bio-docs. What could have been a mere portrait becomes a bigger-picture look at a family of troubled geniuses  – two of whom were marginalised by society, and one of whom turned outré ideas into cult success. NM

33. ‘Trainspotting’ (1996)

A generational manifesto and arguably the great U.K. film of the decade, director Danny Boyle and writer John Hodge’s brilliant Britpoppy take of Irvine Welsh’s cult novel exploded off the screen with a cheeky vigour. It stubbornly refused to mine its grim subject matter (Scottish heroin addicts trying to eke out an existence amid the squalor of modern Edinburgh) for any sort of tight-lipped social realism or moral judgment. While some condemned the film for glamorising heroin usage, the misadventures of Mark Renton (Ewan McGregor) and his gang of “small-time wasters” – including the horrifying scene where our hero hallucinates being menaced by a zombie baby – hardly made a smack habit seem like something to aspire to. This is hardcore. DE

32. ‘The Sweet Hereafter’ (1997)

A ruinous picture about a community torn apart by unfixable tragedy, Atom Egoyan’s exquisite adaptation of Russell Banks’ 1991 novel is heartbreaking even in summary: A school bus plunges into an icy lake, and 14 children are dead. In the midst of this unthinkable moment, a big-city attorney (Ian Holm) arrives in town to “direct their rage” into a class-action lawsuit. Egoyan plumbs the material for delicate fable-like resonances and the darker, buried trauma of failed parenting. Actor Sarah Polley, only 18 at the time of shooting, taps into a blue-bleak vein of survivor’s guilt; her quiet, cryptic turn is the movie’s soul. JR

31. ‘The Big Lebowski’ (1998)

An elegy for the counterculture of the 1960s, a tribute to Raymond Chandler, a loopy shaggy-dog story, a look into the dog-pull-gun-on-dog world of big-league bowling – the Coen Brothers’ eminently quotable cult crime-caper comedy is all of these things and oh-so-much more. Jeff Bridges gives one of his most delightful and enduring performances as the Dude, the White Russian-quaffing, Eagles-loathing paragon of mellowness who finds himself continually dragged into stressful situations beyond his making. Initially considered something of a letdown, The Big Lebowski is one of those films that gets better with each viewing – especially when “doing a J,” Dude-style, is part of the experience. And if you don’t think so, well, that’s just your opinion, man. DE

30. ‘My Own Private Idaho’ (1991)

Gus Van Sant’s third feature weaves together two vital strands of early-Nineties alternative culture: New Queer Cinema and Pacific Northwest grunge. But it’s more fever dream than trend report, following River Phoenix’s tender, narcoleptic hustler from Seattle and Portland to the Midwest (see title), and then to Italy on a quest to find his long-lost mother. Its structure is a patchwork of vignettes, threaded with the Shakespearean tale of the rentboy’s best friend and unrequited crush (Keanu Reeves) and interrupted by a montage of stories from real street kids. The same bracing combination of melancholy and bitter humour that suffuses the best Nirvana songs makes these mismatched elements cohere – and elevates the film beyond the cultural context in which it was created. JB

29. ‘Princess Mononoke’ (1997)

Western audiences first caught wind of the work of Japanese animator Hayao Miyazaki via this dark fairy tale, the story of an exiled prince who gets a demon’s curse put upon him and finds himself caught in the middle of a war between forest spirits and the human ironworkers who threaten to destroy it. This decidedly grown-up cartoon is remarkable for the striking beauty of its imagery, in which leaves blowing in the breeze and severed limbs flying through the air are rendered with equal splendour. And unlike a lot of animation of the time, Miyazaki’s eco-friendly fable didn’t shy away from moral complexity; there are no real bad guys here, only strong personalities whose good intentions are at direct odds. JS

28. ‘Heat’ (1995)

Heralded as the first onscreen pairing between Robert De Niro and Al Pacino since they traded eras – but not scenes – in The Godfather Part II, Michael Mann’s stylish, no-nonsense crime thriller delivers not one but two epic stand-offs between the two acting titans, and an operatic L.A. crime saga truly worthy of their best efforts. The methodology and mentality of both cops and crooks are detailed with painstaking professional verisimilitude, and the question becomes: Do we want these criminal masterminds to get away with their crimes, or get caught by their law-abiding counterparts? Meanwhile, a murderer’s row of A-list supporting actors help turn this influential heist flick into an eclectic portrait of two communities on opposite sides of the law, both battling for survival in a zero-sum game. TGi

27. ‘Three Colours: Blue’ (1993)

Blue isn’t the warmest colour in the first installment of Krzyszstof Kieślowski’s trilogy based on the French flag: It begins with Julie (Juliette Binoche) waking up in a hospital and learning a car accident has killed her husband and child. Grief turns her cold; she’ll slowly, eventually thaw, but not before the filmmaker challenges the entire notion of liberté via his numbed heroine. Few have used the title colour so expressively, whether in the reflection of a sonogram or the swimming pool that Binoche uses to work out her sorrow. A highlight of the Polish director’s filmography and the decade’s arthouse explorations of life, death and rebirth. KYK

26. ‘Magnolia’ (1999)

A dying man calls out to the son he abandoned; a game show host numbs his illness with booze; a whip-smart kid crumbles in the spotlight; a former child prodigy loses his grip on reality. If anyone can thread these seemingly disparate character arcs together into a gripping narrative and pull off a modern-day plague of frogs, it’s Paul Thomas Anderson. Backed by a sorrowful Aimee Mann soundtrack and featuring Tom Cruise’s most memorable performance to date (“Respect the cock!“), this interconnected epic about wising up is a surrealist, quasi-biblical look at life and its odd, amphibian-filled coincidences. To paraphrase narrator Ricky Jay, strange things happen to us all the time – it’s how we choose to deal with them that ultimately define us. AS

25. ‘Out of Sight’ (1998)

Like a Bogart-Bacall romance rebooted for a post-Pulp Fiction world, Steven Soderbergh’s adaptation of Elmore Leonard’s novel pairs George Clooney and Jennifer Lopez as a bank robber and U.S. marshal, respectively, who meet cute in the midst of a prison break. Of course they look like movie stars; of course they fall in love. With its witty dialogue, gritty Detroit backdrop, a stellar cast of supporting players (including Ving Rhames, Don Cheadle, Steve Zahn and an uncredited Samuel L. Jackson) and a killer retro-jazz soundtrack by David Holmes, Out of Sight is loaded with low-key joys. But the film’s greatest thrills come from watching the sparks fly as Clooney (definitively proving he was more than the sum of his E.R. haircut and his nippled batsuit) and Lopez play cat and mouse with each other, despite knowing that their chosen professions will forever keep them apart. DE

24. ‘Rushmore’ (1998)

Wes Anderson’s second film quickly established the dapper, quirky auteur’s style and motifs: the Sixties British Invasion soundtracks, the distinctively attired characters, the cluttered dollhouse sets, the middle-aged mopes yearning for vanished glory. But the way he takes on this love triangle involving an over-scheduled private school teen (Jason Schwartzman), a depressed millionaire (Bill Murray) and a widowed teacher (Olivia Williams) then gives it such an unexpected emotional depth deflects all those he’s-just-a-twee-hipster-with-a-nice-record-collection digs. Even a scene of multiple generations dancing in slow motion to the Faces becomes a tear-jerker. And it’s ground zero for Murray’s incredible sad-sack career second act. NM

23. ‘Eyes Wide Shut’ (1999)

When Stanley Kubrick’s final, posthumous film – a dreamlike journey through a surreal underworld of sex, power and humiliation, starring then real-life husband-and-wife Tom Cruise and Nicole Kidman – opened in the final year of the millennium, there was plenty of grousing: Where was all the down ‘n dirty Tom-Nicole sex we’d been promised? Why did everything feel so slow and unreal? What were those weird music cues? Of course, similar gripes had greeted previous Kubrick films, including The Shining, and much as with that horror masterpiece, Eyes Wide Shut‘s reputation has steadily, deservedly risen. Everything here – from the grimy-yet-beautifully-textured cinematography to the incantatory dialogue, the heightened performances to the red herring-filled plot – serves to create the feeling of a waking dream, one filled with ineffable longing. BE

22. ‘Kids’ (1995)

A teensploitation film fed by fear of AIDS, Larry Clark’s controversial, verité-style debut nonetheless captured a raw, reckless day in the life of real New York City adolescents as told by one of their own: 19-year-old screenwriter/skater kid Harmony Korine. Boys and girls (but mostly boys) unhinge their jaws, and their insatiable appetites expose at least three characters to the HIV virus while another young woman (Chlöe Sevigny, in her breakout role) is sexually assaulted. Kids is a time capsule, and its Lou Barlow-helmed soundtrack gleefully suggests that teens in the Nineties had surrendered to apathy and excess without even an assist from Nirvana. But this putative cautionary tale turned to prophecy when two of the film’s stars (Harold Hunter and Justin Pierce) died tragically within a decade of its release. PR

21. ‘Barton Fink’ (1991)

“I’ll show you the life of the mind!” Joel and Ethan’s Tinseltown adventure finds the brothers at their most wonderfully baffling: Are any of the scenes happening inside the main character’s head? (And, seriously, what’s in the box?) John Turturro is the pompous New York playwright who cashes in on his Broadway success by selling out to Hollywood, which only results in writer’s block, murder and frequent visits from John Goodman’s sublimely unctuous insurance salesman. It’s as much a poisonous showbiz satire as it is a dark portrait of American anti-Semitism – and a film about creative stagnation in which the ideas and inventiveness never let up. TGr

20. ‘Dead Man’ (1995)

Filthy, nasty, funny, ponderous and peyote high, Jim Jarmusch’s anti-Western is the coolest black-and-white slow-burn in all the land. Johnny Depp, back when the man could do no wrong, plays William Blake, a timid accountant whose journey west quickly spirals into violence and vengeful justice. His companion is an unlikely Native American sidekick named Nobody (Gary Farmer); the whole thing may or may not take place in the afterlife. From Neil Young’s staggeringly great, broke-down Morricone-esque score to Iggy Pop as a campfire drag mother, Jarmusch’s deconstructed oater is like a 19th-century nightmare filtered forward into a country that’s no less dumb, guilty or lost. EH

19. ‘Fight Club’ (1999)

David Fincher’s brutally violent, visually stunning adaptation of Chuck Palahniuk’s novel is so perfectly pitched that flippant young punks can see it as call for antisocial mayhem and older establishment types could read it as a repudiation of Nineties nihilism. Give credit to stars Edward Norton and Brad Pitt, two leads who embody the yin and yang of macho self-destruction – especially when a certain killer twist kicks things into a different gear. Though it keenly described the rootlessness of middle-class Gen-Xers, its insights into a specific end-of-the-century alienation still apply: to the anti-materialistic progressives and the alt-right; to #NotAllMen activists and GamerGaters; and to any recklessly angry type who find a community that allows them to indulge their worst impulses. NM

18. ‘Paris Is Burning’ (1990)

Before Madonna appropriated ball culture in “Vogue,” first-time director Jennie Livingston trained her camera on the Harlem-based scene, where “houses” hosted wildly inventive drag battles and functioned as surrogate families for gay men and trans women of colour. Performers speak eloquently on how racism, homophobia and poverty have deferred their lifelong dreams of fame and fortune; one starry-eyed young dancer is murdered. Detractors have accused Livingston of exploiting her subjects, but the film remains a crucial snapshot of a community whose influence might otherwise have been erased by a mainstream culture that plundered it for ideas. JB

17. ‘Toy Story’ (1995)

Nothing looked like Pixar’s tale of action figures and the kid who loves them when the company’s inaugural offering hit screens – fast-forward one decade-and-beyond later, and nearly everything looks like it. As the first full-length computer-animated movie, it was destined to be a historic achievement, but what John Lasseter’s instant classic proved, beyond the obvious marvels of technique, was that CGI could have all the whimsy, warmth and depth of hand-drawn animation in the right hands. The digital sandbox may be cutting-edge, but Woody, Buzz Lightyear and the rest of the gang’s spirit of friendship and adventure feels as old as childhood. ST

16. ‘Reservoir Dogs’ (1992)

Quentin Tarantino’s debut feature set the table for everything that followed: the skewed-chronology storytelling, which turns it into heist movie without a heist; the pop culture references, like the opening disquisition on the true meaning of Madonna’s “Like a Virgin”; and the eclectic soundtrack, which will forever associate Stealers Wheel’s “Stuck in the Middle With You” with the gruesome spectacle of a cop getting his ear sliced off. But Reservoir Dogs would end up being even bigger than than its creator – it’s the opening salvo to an indie revolution. After an era dominated by Merchant/Ivory productions, a wave of bloody genre films suddenly turned the arthouse into the grindhouse. Things would never be the same. ST

15. ‘The Matrix’ (1999)

The major sci-fi film of 1999 was supposed to be The Phantom Menace – and then a true mind-bender emerged, setting the agenda for the next century’s blockbusters. The Matrix is a dazzling combination of radical political messaging, kick-ass action sequences and a brilliant premise: Anonymous hacker Thomas Anderson (Keanu Reeves) learns that he’s living in an elaborate simulation orchestrated by robots that have enslaved humanity; naturally, only he can stop it. Filmmakers Lilly and Lana Wachowski brought the world bullet-time visual effects and wire-fu fight scenes, grafting a postmodern hipness onto a classic hero’s journey. But just as meaningfully, they tapped into the culture’s pre-millennium tension, envisioning a frightening near future in which humanity would be ruled by the very technology it had created. TGr

14. ‘Boogie Nights’ (1997)

Imagine Robert Altman’s Nashville raunchily transplanted to the San Fernando Valley – with a couple of bloody, Tarantino-esque shoot-outs thrown in for kicks. And boom, you have Paul Thomas Anderson’s sprawling tale of the late Seventies/early Eighties porn business, an epic group-character study that totally nails the effervescent sleaziness of the last days before AIDS without ever settling for easy disco-ball nostalgia. Julianne Moore, Don Cheadle, John C. Reilly, William H. Macy and Heather “Rollergirl” Graham are all unforgettable as members of director Burt Reynolds’ dysfunctional porn family, while Mark Wahlberg’s breakout turn as priapic prodigal son Dirk Diggler put his Marky Mark days behind him forever. It’s the announcement of a bold new filmmaking talent, a beautiful look back and a hint of things to come. DE

13. ‘Fargo’ (1996)

Joel and Ethan Coen’s darkly comic snowbound noir stars William H. Macy as Minnesota car salesman Jerry Lundegaard, a Midwestern every-schmo who hires a couple of small-time criminals (Steve Buscemi and Peter Stormare) to kidnap his wife in the hopes of pocketing the ransom money once her wealthy father pays up. Like almost everything this would-be criminal mastermind touches, though, the plan goes wildly off the rails. People end up dead, things fall apart and pregnant police chief Marge Gunderson (Frances McDormand in a iconic, Oscar-winning performance) is determined to doggedly trace the blood trail back to its hapless source. It’s a startlingly original procedural, one that deftly pairs sweet-natured satire – those accents! – with shocking violence – that woodchipper! – and slowly, ever-so-politely emerges as one of the standout gems of the Coens’ considerable career. GM

12. ‘Beau Travail’ (1999)

Behold, the Foreign-Legion reimagining of Billy Budd you never knew you needed. French director Claire Denis takes Herman Melville’s final novel of military life and mancrushes, drops it into modern-day West Africa and turns the story of a handsome rookie recruit (Grégoire Colin) and an envious sergeant (Denis Levant) into an impressionistic dismantling of first-world masculinity. Cinematographer Agnes Godard films scenes of blinding daytime marches and late-night club revelries with a palpable sense of heat; using everything from opera arias to Neil Young’s “Safeway Cart,” Denis transforms the troops’ manoeuvres into musical numbers. Coming at the end of the decade, this landmark movie felt like a breath of fresh, and equally humid-as-hell air blowing into an often stale late-Nineties’ Euro-arthouse scene. And just when you think things can’t get anymore dynamic, Corona’s “Rhythm of the Night” comes on, Levant hits the dance floor and you fall into a state of delirium. DF

11. ‘Groundhog Day’ (1993)

Caddyshack meets A Christmas Carol in Harold Ramis’s warm-hearted, wisdom-filled comedy, as Bill Murray’s self-important TV weatherman gets his karmic comeuppance by reliving the same small-town Pennsylvania day over and over until he gets it right. The movie star is at his wise-guy best here, playing a blithely sarcastic sexist who initially views his metaphysical predicament as a license to indulge in bad behaviour consequence-free. Then he bottoms out and eventually realises that he’s better off becoming a standup guy. Nineties rom-com queen Andie MacDowell is the woman who wins his heart. (Bonus rewatch surprise: a young Michael Shannon in his feature film debut as one half of a newly married couple very excited about Wrestlemania tickets.) Repeat viewings are essential. GM

10. ‘The Piano’ (1993)

Merchant-Ivory monopolised prestige period films until Jane Campion’s strange, unruly, expressionistic fable shattered everything. Holly Hunter stars as Ada, a mute 19th century mail-order bride sent with her precocious young daughter (Anna Paquin) from Scotland to New Zealand to be with a fussy husband (Sam Neill). Her piano is her only voice, refused until a rough neighbour (Harvey Keitel) trades land for the instrument. The brute agrees to return it to Ada for lessons that belie his burgeoning love – and, eventually, hers. The startlingly original gothic romance beguiled the Cannes Film Festival, making Campion the first woman ever to win the Palme d’Or. Oscar noticed, too: Hunter and Paquin nabbed acting awards, while Campion won Best Screenplay. SG

9. ‘Chungking Express’ (1994)

You only need to watch Wong Kar-wai’s ode to all the lonely people once to permanently alter your consciousness – after that, you’ll never be able to hear “California Dreamin'” without imagining Faye Wong dancing to it. The Sixties rock song is only one of many all-over-the-map influences the Hong Kong-based director imports into the fluorescent-lit film’s twinned tales of the lovelorn and the lost. Characters sewn together from spare bits of Old Hollywood and French New Wave archetypes sip Mexican Sol Cerveza and frequent a takeout joint where gyro meat spins on vertical rotisseries. The heroes of this chaste romance are two cops struggling to move on after breakups; one becomes infatuated with an outlaw in a blonde bombshell wig, while his doppelganger is covertly courted by a gamine who sneaks into his apartment to clean. More distinctive than even the lovers’ charming quirks is Wong and cinematographer Christopher Doyle’s smudgy, impressionistic visual style, which immerses the viewer in a celluloid dreamscape that only adds to its swooning potency. JB

8. ‘Malcolm X’ (1992)

Spike Lee had hoped that his biopic about the slain Civil Rights leader would have the epic sweep of classic movies like Lawrence of Arabia and Gandhi. In fact, the director achieved something even greater: A historical drama, a compelling character study and a political essay all at once. As we watch Malcolm (played by Denzel Washington in one of the finest performances anyone anywhere has ever given) go from happy-go-lucky party-boy to smalltime hoodlum, convict to rabble-rouser, political leader to family man and beyond, we see how the cumulative impact of the lives he’s lived come to transform his thinking. This is not a historical portrait captured in amber; it’s a living, breathing movie that is as much about the here and now as it is about the mercurial era of its subject or the moment the movie was released into theatres. BE

7. ‘Slacker’ (1991)

The London Calling of Nineties cinema arrived at the exact pivot between one decade (and one America) and the next. Richard Linklater’s career-long obsession with time – what it does to us and what we make of it – starts right here. Dispensing with plot, recurring characters and fixed locations, this free-form excavation of Lone Star eccentricity wanders around Austin, Texas, trailing the talky troubadours of a generation defeated by Reagan and prepped for Clinton-era cynicism. It’s a chronicle of its moment, encapsulating the bar-stool conspiracies and nihilistic philosophies of a very specific post-post-hippy college town, while also absolutely nailing an evergreen sense of uneasy freedom, U.SA.-style. All this and Madonna’s pap smear results, ready for sale. EH

6. ‘Close-Up’ (1990)

Awakening Western eyes to a global strain of sympathy that knew no borders, Iran’s Abbas Kiarostami was the art-house “discovery” of the 1990s: a tenderhearted humanist who gave lie to the reductive politics of the day. Kicking off the decade he would come to dominate, Kiarostami released this radically original docu-fiction hybrid, flecked with sneaky humour and a deeper anxiety about borrowed notions of identity. On its surface, the film is the story of a con artist: Hossain Sabzian loves movies and wants to be famous. Somehow, he doesn’t have a problem lying to a stranger that he is well-known Iranian director Mohsen Makhmalbaf. One thing leads to another, and our bogus hero is invading a family’s home under false pretences, all while digging himself deeper into a colossal pit. Close-Up extends the ruse into a feature-length cringe – until it drops its gloriously compassionate endgame, a meta-touch that helped push the medium into uncharted territory. JR

5. ‘Pulp Fiction’ (1994)

Take two chatty hitmen. Add in a coke-snorting femme fatale, her mobster husband, a boxer on the run, some basement dwelling hillbillies and a low-rent Bonnie and Clyde robbing a diner. Drench the whole thing in the comprehensive pop cultural obsessions of its creator, and voila – you have the Royale With Cheese of 1990s independent cinema. No other film of the decade had the instant adrenaline-shot-to-the-heart impact of Quentin Tarantino’s love letter to the films that formed his cinemania – it doesn’t feel like a defining movie of the decade so much as the Nineties itself, achingly hip and deliriously footnoted and endlessly quotable. Posters hung on dorm walls; parodies sprouted up overnight; even the soundtrack, filled with extremely well-curated surf rock and vintage smooth R&B, was inescapable. Building on the rat-a-tat dialogue and funny-to-violent whiplash of his debut Reservoir Dogs, Tarantino’s sophomore movie is where his signature style really comes into its own – few other filmmakers can claim to have their surname turned into a adjective after just two features. We’re still feeling the aftershocks of this seventh-art earthquake decades later. BT

4. ‘The Silence of the Lambs’ (1991)

The infamous mask, those giant moths, the grotesque handiwork of not one but two chillingly nicknamed homicidal maniacs, “I ate his liver with some fava beans and a nice Chianti” – it’s been decades since Jonathan Demme’s serial-killer thriller swept the Oscars and scared the beejesus out of audiences, and none of its indelible images or best lines have faded from our collective memory. The late, great director and screenwriter Ted Tally immediately makes you complicit in this Faustian bargain between Jodie Foster’s promising FBI cadet Clarice Starling and Anthony Hopkins’ savage bon vivant Hannibal Lecter – every conversation with Hannibal Lecter turns into a strange, singular flirtation. (Which doesn’t mean the creators ignore the era’s casual chauvinism; check out the way Demme frames the library assistants staring Starling down.) Everything plays out like a perverse Pygmalion: She deciphers his enigmatic clues while he isolates the trauma that makes her tick and schools her in the proper etiquette of the psychopath. Clarice is warned not to let Hannibal into her head, but she does – and now we’ll never get him out of ours. PR

3. ‘Safe’ (1995)

It starts with a truck farting out fumes, or maybe it’s that “totally toxic” new couch: For some reason, San Fernando Valley housewife Carol White (Julianne Moore, brilliantly brittle) is sick. The spooky genius of Todd Haynes’ near-abstract masterpiece is that it never pins down an answer (Fruit diet? A chemical-heavy perm?), putting us on exploratory paths that few movies dare. Set in a soulless, deodorised 1987 but very much of its right-here-right-now moment, Safe plays like an indictment of suburban America: “Where am I?” Carol asks, on the verge of mental collapse. Hyperventilating at a friend’s baby shower, she could be reacting to expectations she can’t meet. Unspoken by name is the AIDS virus, for which the film is often read as a metaphor. But this indie-cum-disease-of-the-week thriller extends far beyond even that diagnosis, into the kind of existential ennui that would make Michelangelo Antonioni beam. Provocatively, Haynes gives his timid character the impulse to make a change – but at what cost to her freedom? It’s a movie that will frighten you of just about everything. JR

2. ‘Hoop Dreams’ (1994)

The movie that smuggled long-form observational documentary into multiplexes, gave birth to a generation of filmmakers and made mass audiences reckon with the challenges of being young, poor and black in America – the one that Roger Ebert called “the great American documentary.” Shot over six years and presented over three breathless hours, this Oscar-nominated epic from filmmakers Steve James, Frederick Marx and Peter Gilbert follows teenagers William Gates and Arthur Agee, wildly talented basketball players from Chicago’s south side, as the young men go from playground to gymnasium, from courtside dramas to myriad struggles at home. Even a quarter of a century later, with its protagonists having drifted into middle age, Hoop Dreams still plays like a buzzer beater. And that’s because it tells a story still largely unheard in popular art, one that comes alive through a gathering of complex, intimate details, and takes the time to trace the twists and turns, thrills and indignities that only real life can offer. It’s a full-on, time-tested American masterpiece. EH

1. ‘Goodfellas’ (1990)

“As far back as I can remember, I always wanted to be a gangster.” Martin Scorsese’s woozy, dizzy adaptation of Nicholas Pileggi’s slice-of-Mafia-life book Wiseguy is many things: a social anthropology study, an epic look at the American Dream, a coked-up nightmare, a nostalgic look back at an age when made men were made men, a head-spinning display of virtuosic filmmaking, the blueprint for the modern organised-crime saga and a peerless look at a world where you might be slapped on the back or shot in the face. “Mob guys love it, because it’s the real thing,” Pileggi told GQ. “They say, ‘It’s like a home movie.'” And as you watch Ray Liotta’s Henry Hill go from up-and-coming crook to cosa nostra bigwig to Witness-Protection-Plan “average nobody,” you realise you’re getting a funhouse-mirror reflection of an old-fashioned U.S. of A. bootstrap success story, complete with bespoke Italian suits, bulging cashrolls and Bolivian-marching-powder meltdowns.

Every performance, from the holy trinity of Liotta, Robert De Niro and Joe Pesci (“Funny like I’m a clown, I amuse you?”) to the round-the-way guys in the background, feels pitch-perfect. Its movie-mad references run the gamut from The Godfather to The Great Train Robbery; its soundtrack incorporates everything from Bobby Darin to Donovan, the Stones to Sid Vicious. (After that murder montage, filmmakers are essentially forbidden from using Layla’s coda to score a scene ever again.) Its influence is incalcuable – you don’t get a million moving-camera showstoppers without that Copacabana tour, and you definitely don’t get the Tarantino, et al., mix of black humour and horrifying violence without Goodfellas‘ getting that combination down to a science first. And though Scorsese had made great movies before and would make great ones after this, this Mob-flick hit feels like a summation of his culturally specific, universally thrilling cinema about men on the edge. There are movies that may be more emblematic of the Nineties, but this was the one that set the pace for the entire decade – a high mark that left most other contenders to the throne looking like schnooks. DF