The 99 Best Movies of 1999, Ranked

In 1988, Stephen Frears’ Dangerous Liaisons arrived in theaters and got a bunch of Oscar nominations. Director Roger Kumble’s 1999 update of the same material may not have taken the Academy Awards by storm, but it’s admittedly a lot more fun. This modern-day spin on the French novel by Pierre Choderlos de Laclos stars a supremely bitchy Sarah Michelle Gellar as the conniving and coke-snorting Kathryn Merteuil, who bets her stepbrother Sebastian (Ryan Phillippe, offering so many sexual awakenings), that he can seduce their high school’s virginal new girl Annette Hargrove (Reese Witherspoon). It’s an over-the-top marvel — see: the spit dangling between Gellar and Selma Blair’s mouths as they practice kissing — but also a devilishly smart bit of translating something so wonderfully trashy from page to screen. —E.Z.

A One Flew Over the Cuckoo’s Nest for a new generation, this somber drama drew from the memoir of Susanna Kaysen, who at 18 was forced into a psychiatric hospital and diagnosed with borderline personality disorder. Winona Ryder plays Kaysen, and director James Mangold surrounds her with some of the then-brightest up-and-coming actors, including Clea DuVall, Elisabeth Moss, Jared Leto, and the late Brittany Murphy. But, of course, the film is best remembered for Angelina Jolie’s volcanic performance as Lisa Rowe, a fellow patient who has spent much of her life institutionalized. A rebel spirit and a deeply troubled soul, she’s the film’s bruised heart, and Jolie brought her to such impassioned life that her Oscar win for Best Supporting Actress was practically a foregone conclusion. —T.G.

Take a hit of dramamine before cueing up Oliver Stone’s note-perfect take on the NFL, made just as the organization was exploding in commercialism and excess. Centered on the fictional Miami Sharks, the film is as much an exploration of politics, power, greed, and warfare as any of the director’s other works, featuring a cutthroat owner (Cameron Diaz), an aging star QB (Dennis Quaid), an upstart third-stringer with an overactive ego (Jamie Foxx), and a coach in his twilight (Al Pacino, finally finding a role in which SHOUTING certain WORDS is wholly appropriate). Yes, it can feel like being sucked into an episode of MTV Spring Break on an eight ball. But it’s also a prescient look at a powder-keg league rife with problems, from liberal use of painkillers to highly questionable concussion protocols. Throw in some incredible NFL-great cameos — from Lawrence Taylor as, what else, a linebacker and Jim Brown as a defensive coach to Easter-egg appearances by the likes of Dick Butkus, Barry Switzer, and Johnny freaking Unitas — and it’s got a reasonable claim to being one of the best football movies of all time. —M.F.

In which director Stephen Sommers conjures up an old-fashioned Thirties-serial-style romp that had been D.O.A. since Indiana Jones hung up his fedora after the original trilogy, and Brendan Fraser makes a strong case for being one hell of an action hero. The shambling, bandaged creature had been considered by many to be the weak link in the Universal monster stable back in the day (though for the record, we stan a legend regarding Boris Karloff’s supremely creepy take on Imhotep). Reimagined for this late-Nineties blockbuster, however, the Egyptian high priest — awakened from his millennia-long slumber by Fraser’s treasure hunter and Rachel Weisz’s aspiring archeologist — is an unstoppable, supernatural force of immense CGI evil. Throw in flesh-eating scarabs, a whole army of zombies, a sandstorm that takes the face of the vengeful holy man, and some great chemistry between the two leads, and you have the basis for a potent thrills-chills-spills throwback. You can thank this franchise for Dwayne Johnson’s screen career as well, since its spinoff The Scorpion King helped sell the wrestler as big-screen crossover material. —D.F.

Released mere weeks after The Matrix captured the zeitgeist on the way to becoming a blockbuster, David Cronenberg’s loopy, entrancing sci-fi/horror offered its own take on alternate realities — one with far more gross-out shocks than bullet-time razzle-dazzle. Set in the year 2030, when a celebrated virtual-reality game designer (Jennifer Jason Leigh) is about to unveil her coolest product yet — right before she’s nearly assassinated — Cronenberg’s vision of the future simply seemed too perverse for its era. (His reliable penchant for designing high-tech gizmos that look disgusting and/or sexual remains an easy way for him to scare off the fainthearted.) But now that the 2030s are in spitting distance, this disturbingly hilarious portrait of a hellscape in which humanity has inexorably merged with its technology feels all too prescient during an age when social media dominates our lives and A.I. willfully distorts our conception of what’s real. Sure, Existenz’s prediction that we’d be jacking our video games directly into our spines was off — at least so far. But don’t get too smug: We’ve still got six years until his “future” is right at our doorstep. —T.G.

“Oh, and this one time, at band camp…” Director Paul Weitz’s tale of four high school friends trying to lose their virginity before the end of senior year melds the gross-out comedies of the early 1980s with the sensitive, more realistic John Hughes teen movies of the mid-Eighties, and somehow finds the perfect middle ground while updating it for the Blink-182 era. (Bonus: You even get to hear Mark Hoppus himself sing “Go Trig Boy, it’s your birthday!”) Has there ever been a more awkward father-son sex talk than Eugene Levy trying to explain the birds and the bees to son Jason Biggs via porn mags? Or a more cringe-inducing deployment of premature ejaculation(s) as a punch line than the Porky’s-friendly sequence involving Shannon Elizabeth, a webcam, and Biggs’ striptease fail? It inspired dozens of sequels and spin-offs, and introduced the greater world to a gaggle of next-gen talent (Chris Klein, Natasha Lyonne, Tara Reid, Mena Suvari, Seann William Scott), the regrettable term MILF, and the joys of fucking apple pies. And Alyson Hannigan’s banger of a prom-night confession, delivered in the sunniest manner possible, remains the best spit-take-inducing joke of ’99. —D.F.

After directing a series of acclaimed shorts, Lynne Ramsay made her remarkable feature debut — a haunting Scottish drama about a boy (William Eadie) who accidentally drowns a friend while rough-housing. He’s then forced to carry the guilt for a killing he can’t tell anyone about. One film in, and the filmmaker who would one day give us We Need to Talk About Kevin was already displaying an impressive understanding of the complexity of childhood, shaping a period drama in which poverty and poetry coexist. Yet she also focuses on the immediacy of her characters’ reality, showing how James’ unhappy life nonetheless contains moments of fleeting joy and wonder. It was the beginning of what continues to be one of the most impressive filmographies of the 21st century. —T.G.

In 1997, many American music-lovers were unfamiliar with the talents of Cuban musicians like Ibrahim Ferrer and Rubén González. Then came Buena Vista Social Club, an album (masterminded by American producer Ry Cooder) that gathered together the island’s best singers and players for a showcase of songs and musical styles that had been largely unheard outside of the country. Wim Wenders’ ravishing documentary chronicles both the making of the record and the celebratory concerts the musical collective later gave in Amsterdam and the U.S., all of which suddenly turned these once obscure artists into international superstars. Like the LP, the movie became one-stop-shopping for outsiders seeking a guide to the country’s rich musical history, and thanks to Wenders’ clear affection for these Cuban legends, we were all invited to share in this very special club. —T.G.

Remember how batshit everyone went when the trailer dropped for the first new Star Wars movie in 16 years? It teased new worlds, new creatures, new characters — like some guy who looked the devil and had a double-edged lightsaber!!! Liam Neeson and Samuel L. Jackson would play elder Jedis. Natalie Portman was cast as the future mom of Luke and Leia. Ewan McGregor would give us Obi-Wan Kenobi in his younger, hotter years. No less than George Lucas himself was coming back to direct what would be the first in a new trilogy of prequels, which would trace how Annakin Skywalker started his journey from being a boy kicking it on Tattooine to the wheezing embodiment of evil. It was arguably the single most-anticipated movie of all time, people lined up for days outside of theaters to be the first to see it, and… well, you know the rest. You only have to say “Jar-Jar Binks” to start a full-blown argument among fans. In 1999, The Phantom Menace looked like it was coasting on being something from out of the past. Watch it now, however, and you’ll realize that this divisive addition to a beloved franchise doubles as a sneak peek at what the next quarter-century of movies would like. Dis is nutsen, indeed. —D.F.

It’s The Taming of the Shrew, teen-comedy style. Located right at the genre’s midpoint between Clueless and Mean Girls, this spin on the Bard’s romance relocates the bawdiness and bickering to a high school in Tacoma, Washington, where Bianca Stratford (Larisa Olyenik) is being wooed by not one but two suitors: a handsome, douchey big-man-on-cambus (Andrew Keegan) and a shy, sweet new student (Joseph Gordon-Levitt). She can’t date anyone until her older sister Kat (Julia Stiles) does, however. So the resident school rebel Patrick (Heath Ledger) is “hired” to take her out, instantly butting heads with this independent woman — and that’s when director Gil Junger’s movie finds its spark. The chemistry between Stiles and Ledger is off the charts; though the latter is still years away from his lovelorn cowboy and psychotic clown roles, you can see the this-guy’s-a-movie-star charisma radiating off him. Yes, some of it has not aged gracefully — the Save Ferris and Letters to Cleo performances carbon-date the proceedings, and let’s never again mention how Kat gets her prospective beau out of detention. But watch Ledger sing “Can’t Take My Eyes Off of You,” or Stiles drunkenly dancing on a table to Biggie, or any moment when they share the screen together. You can instantly think of a million things you love about it. —D.F.

After Pulp Fiction redefined independent cinema in the mid-1990s, everyone and their mom started making movies populated with smooth-talking criminals and ironically intersecting storylines. By the time screenwriter John August and director Doug Liman got around to contributing their reluctant addition to this sub-subgenre near the decade’s end, however, they’d wisely ixnayed the pulp hipsterdom and simply kept everything else that worked. The result is leagues better the era’s typical Tarantinoesque clones, starting with an exchange between three grocery store employees (Sarah Polley, Katie Holmes, and Desmond Askew) and branching off into a triptych of misadventures: a desperate, amateur drug dealer gets in way over her head; a trip to Sin City — Vegas, baby! — goes awry; two closeted actors have two dangerously close calls with fate. Mind-reading cats, car chases, and a tantric threesome that ends in a three-alarm fire get thrown in for good measure. The soundtrack makes for a great millennium’s-end time capsule (“Gangster Trippin’,” “Steal My Sunshine,” a remix of “The Macarena”), and it gives a taste of what was to come from Liman, Polley, a pre-Deadwood Timothy Olyphant, and Taye Diggs. The movie’s title isn’t just a command issued in all three narratives — given the movie’s barreling forward momentum, it’s closer to a statement of purpose. —D.F.

Normally, the news that aspiring author Harper Stewart (Taye Diggs) would finally be publishing his debut novel should be a cause for celebration among his tight clique of old college buddies. Except one of his pals has procured an early copy of the book, which is a thinly veiled take on the gang’s misadventures, indiscretions, and hush-hush hookups. And once everybody reunites for the wedding of their good friend Lance (Morris Chestnut), a shit-ton of revealed secrets and rekindled old flames — notably between Harper and Jordan (Nia Long), a.k.a. the one that got away — threaten to derail the celebration. Writer-director Malcolm D. Lee uses this typical Big Chill-ish scenario as excuse for a lot of real talk about love, sex, monogamy, fidelity, and the curse of the wandering eye; there are a few bull sessions between Diggs and the male members of the group that are so raw that you feel like you’re eavesdropping. It helps that Lee has also assembled one of the best ensemble casts of the class ’99: Diggs, Chestnut, Long, Harold Perrineau, Terrence Howard (who nearly steals the movie), Sanaa Lathan, Monica Calhoun, and a pre-Scary Movie Regina Hall. It deservedly spawned a sequel and a limited series that revisited the characters battling the middle-aged blues. —D.F.

Meet Fred A. Leuchter, Jr., who made a career out of trying to develop a more humane form of capital punishment. He’s an awkward individual who seemed to have noble intentions — so how exactly did he go from there to becoming an infamous Holocaust denier? Documentarian Errol Morris has often been drawn to complicated, sometimes infuriating individuals (who else has devoted entire movies to Robert McNamara, Donald Rumsfeld and Steve Bannon?), but 25 years later, Leuchter stands as perhaps the director’s most baffling and pathetic subject, a man seduced by his faulty logic and desire to be liked, even if it’s by neo-Nazis. Back in 1999, it was perhaps easy to laugh off Mr. Death’s portrait of vanity and stupidity. Now, it feels like a warning we didn’t heed. —T.G.

Jim Jarmusch brings his deadpan-cinephile, downtown-cool sensibility to that most popular of crime-flick stories — a hit man on the run — and adds in bits of Japanese samurai dramas, Chinese martial-arts movies, Italian Mafia sagas, and NYC hip-hop culture to spice things up. Forest Whitaker is the professional killer they call Ghost Dog, an enigmatic figure who communicates with his syndicate connect via carrier pigeon and adheres to a strict, centuries-old Bushido code. When he shows mercy during a job, the local capos decide he needs to be rubbed out. Bad decision, guys. Coming shortly after his revisionist Western masterpiece Dead Man (1995), this homage to a half-dozen genres was seen as a baby step backward by a lot of Jarmusch’s die-hard fans. But time has been extraordinarily kind to his singular remix of an old warhorse narrative, Whitaker’s muted Zen-master performance now seems like a strong career-best contender, and RZA’s score still sounds both perfectly of its time and ahead of it. Bonus points for letting Cliff Gorman get in a couple of bars of “Cold Lampin’ With Flavor Flav” before his demise via a clever sink-drain assassination as well. —D.F.

It was the 1999 movie that boldly goes where no other comedy has gone before, courtesy of a high-concept question: What if the cast of a vintage, cult sci-fi TV show were mistaken as a real-deal starship crew by actual aliens, and were recruited to fight an actual extraterrestrial bad guy? Any similarity to IRL series with beaucoup nerd cachet is, of course, not the least bit coincidental. Yet the movie’s ribbing of overzealous Trekkies, the cosplay-convention circuit and actors milking their bygone 15 minutes of fame is nothing if not affectionate. Plus it’s blessed with a to-die-for ensemble, all on point: Tim Allen nails the Shatneresque bluster, Sigourney Weaver counters his chaunvinistic come-ons with a first-rate eye roll, Alan Rickman hits the perfect note of disdain (“I played Richard III! There were five curtain calls!”), Tony Shaloub plays it cool as an unflappable faux-engineer and Sam Rockwell frets about the mortality rate of former bit players. Released at Christmas time with little fanfare and few expectations, Galaxy Quest ended up becoming a cult favorite about the joy of taking cult favorites seriously. Superfandom — the final frontier. —D.F.

A salute to Douglas Sirk, motherhood, All About Eve — and to acting itself — Pedro Almodóvar’s most celebrated film finds him fully erasing the line between camp and tearjerking drama in this story of Manuela (Cecilia Roth), who’s coping with the tragic death of her teenage son by seeking out his long-absent father. Along the way, she meets several individuals (including Penélope Cruz as a pregnant, HIV-positive nun) in need of a mother figure. Here’s where Almodóvar began his ascension from beloved international filmmaker to mature artist, sacrificing none of the impish humor of his early work while marshaling an emotional sophistication and cinematic mastery (including some lovely references to Hollywood’s classic era) for a movie that, at its core, is a valentine to those whose invisible labor holds up society. —T.G.

The late Iranian auteur Abbas Kiarostami (Close-Up, Taste of Cherry) capped off his remarkable decade with this beautiful, slippery meditation on life, death and the tension between haves and have-nots. A filmmaker (Behzad Dourani) from Tehran travels with a skeleton crew to a small Kurdish town, in order to document the presumed imminent death of a 100-year-old woman and the village’s unique grieving rituals. But as he gets to know the townspeople, his project hits an unlikely roadblock: The elderly resident won’t die. Kiarostami often told stories about people in rural or impoverished settings. Here, he’s questioning how much he’s exploited such people for such artistic expression, and that self-critique adds another dimension to a movie that’s invites us to look beyond our preconceived notions and consider the delightful complexity of those around us.   —T.G.

It was the film that asked the eternal question: Can a normie bookstore owner find true happiness with one of the most famous movie stars in the world? The answer: Yes, but only if she is just a girl, standing in front of a boy, asking him to lover her; and he is Hugh Grant. One of the best romantic comedies of the ’90s, screenwriter Richard “Four Weddings and a Funeral” Curtis and director Roger Michell’s modern riff on Roman Holiday benefits from the meta-casting coup of having Julia Roberts play a dream version of an A-list celebrity not unlike, well, Julia Roberts. The idea of pairing her with fellow rom-com royalty Grant — post-scandal but very much at his charming, stammering best — and a number of supporting players from the Curtis repertory company (Gina McKee, Tim McInnery, Emma Chambers, Hugh Bonneville) now seems like a no-brainer in retrospect, and not even the occasional cloying exchange can keep this from being a high point of the genre. Bonus points for Rhys Ifans’ “masturbating Welshman” take on the world’s worst roommate. —D.F.

So much of the 1990s was spent chasing the next potential Tarantino, leaving nothing but a glut of smooth-talking criminals and empty-calorie coolness in its wake. Still, when word started percolating from across the pond that a young British filmmaker had finally figured out how to mix the ha-ha, the bang-bang and the hip music cues in a way that felt fresh, American ears perked up. And sure enough, when Guy Ritchie’s debut about a group of colorful underworld types united by a pair of stolen vintage guns finally hit our shores in March of 1999, folks were relieved that the movie lived up to its hype. This mash-up of grifters, geezers, cockney slang and a whole lotta U.K. lad culture introduced the world to future action hero Jason Statham, and kicked off a whole new wave of odds-and-sods Brit crime flicks. It was such a successful formula that Ritchie himself would keep returning to it (see: The Gentlemen) even after he’d established himself as a go-to Hollywood guy. It’s definitely dated — but still well worth a butchers. —D.F.

1999 was the breakout year for the ultra-prolific Japanese auteur Takashi Miike, courtesy of the double shot of his unhinged cop-vs.-yakuza epic Dead or Alive and this deceptively calm, altogether more unsettling J-horror movie hitting international film festivals. It’s the latter that most people bring up first when they talk about Miike’s ability to get under your skin, however, thanks to the way he literally gets under the skin of his unlucky protagonist here. Following the overall arc of Ryu Murakami’s novel, this instant classic observes a widower (Ryo Ishibashi) setting up a fake TV-show in order to “audition” a new wife. He settles on a former ballet dancer named Asami (Eihi Shiina), who appears to be the epitome of the docile, dutiful female. Spoiler: She isn’t. Once a still, lumpy sack in the background of a shot suddenly starts moving around, the film shifts into another gear entirely — and even with that warning that the power dynamic will change, you’re still not prepared for what comes next. Even hardcore horror fanatics had to cover their eyes during the final 20 minutes. A psychotronic star was born. —D.F.

Patricia Highsmith’s upwardly mobile sociopath had slithered his way to the screen a number of times, from Alain Delon’s Adonis-lookalike drifter in Purple Noon (1960) to Andrew Scott’s shifty-eyed grifter in the recent Netflix series Ripley. Director Anthony Minghella’s adaptation gives us what may be the most user-friendly version of Tom Ripley to date, courtesy of a fumbling, forever yearning Matt Damon — yet don’t be fooled by the baby face. Popular literature’s chameleonic Great Pretender is still as class-thirsty as ever here, still craves the good life that’s been denied him, and still willing to kill to keep from being exposed as a fraud. Not even Minghella’s lean toward sympathy for his antihero near the film’s end can wash away the talented young man’s sins. The retro ring-a-ding glamor of late 1950s Europe looks incredible, Jude Law and Gwyneth Paltrow radiate the exact kind of taken-for-granted privilege that make the upper crust seem envious and exploitable, and both Cate Blanchett and Philip Seymour Hoffman prove that first-rate actors can make even the most peripheral supporting roles unforgettable. (The latter’s noxious, aristocratic party boy even gets the film’s best entrance.) —D.F.

Right at the moment that Pixar was shaping animation’s future through dazzling computer graphics, Brad Bird reminded viewers of the pleasures of the old school, merging hand-drawn warmth with more cutting-edge techniques. A creative consultant during The Simpsons’ glory days, he crafted his first feature as a gentle tribute to the familiar boy-and-his-dog narrative — except, in this case, the dog just so happened to be an interstellar robot who crash-lands on the East Coast during the height of the Cold War. Without irony or preciousness, The Iron Giant was simple but not simplistic, focusing on the budding friendship between the lovable everyday kid Hogarth (voiced by Eli Marienthal) and the kindly Iron Giant (a pre-Groot Vin Diesel), who the government thoughtlessly wants to destroy. Bird would later team up with Pixar for the hip, stylish Incredibles films, but this E.T.-like gem has even greater heart. Indeed, it’s hard for either adults or their children to watch this movie’s emotional ending without blubbering — you’ll believe a robot can be Superman. —T.G.

It’s absolutely hard to deny the power of the central image that defined German director Tom Tykwer’s breakout hit: Star Franka Potente, hair dyed Little Mermaid-red, running through Berlin in a tank top and light green pants. (Frankly, this hero would look as at home in 2024 Bushwick as she did in 1999 Berlin.) She’s Lola, a woman on a desperate mission to find 100,000 marks so her boyfriend won’t be killed after leaving the money on a train. But this rocket-fueled blast is also a burst of creativity from start to finish, and the filmmaker (who also co-wrote the propulsively clubby music) throws everything at the wall — animation, flash forwards, fantasies, rewinds, you name it — to keep the forward momentum going. And going. And going…. —E.Z.

It wouldn’t be so dismaying to see Pixar become a franchise factory if every sequel was as good as the studio’s first. Originally conceived for a direct-to-video release before all involved saw the potential to go bigger and bolder, the second adventure for the prized playthings of Andy’s room doesn’t just match the dazzling, whirligig slapstick of its predecessor. It also deepens that classic’s themes, confronting cowboy doll Woody with a bona fide moral dilemma that puts his values — alongside his frayed fabric limbs — under the microscope. Meanwhile, a flashback of love and innocence lost, accompanied by a Sarah McLachlan ballad, pioneered Pixar’s diabolical tendency to leave not a dry eye in the room. This is the kind of richly realized continuation that redeems the very idea of sequels. —A.A.D.

Mike Judge may not have set out to make the ultimate workplace comedy — or one of the most quotable movies of the past quarter century — with this story of a frustrated, uptight white-collar grunt (Ron Livingston) who’s accidentally hypnotized into a IDAGF state of Zen. But go up to almost any group of people between the ages of 25 and 55 and ask them if they’ve put one of the new cover sheets on their TPS reports, or how much “flair” they’ve got on, or who took your red stapler. Most of them will start parroting Office Space lines back to you ASAP. It’s impossible to single out one comic performance out of the dozen or so that Judge’s crack ensemble deliver (though we stan the legend that is Diedrich Bader’s mulleted next-door neighbor), but what makes this takedown of the everyday indignities of professional cubicle life so hilarious is how recognizable this collection of archetypes are. If you’ve ever worked in an office, you almost assuredly know some like Gary Cole’s oily boss, David Herman’s rap-loving bro, Stephen Root’s social misfit or Richard Riehle’s middle-aged worrier. And really, who hasn’t wanted to beat a malfunctioning printer to death?! —D.F.

Kimberly Peirce was a film student at Columbia University when she happened to read an article in the Village Voice, about a trans man who’d been murdered in Texas. After her debut feature was released, the name Brandon Teena became synonymous not just with the dangers faced by trans people in a world hostile to their existence, but also the joy and liberation of living one’s truth. Hilary Swank deservedly won an Oscar for playing Teena, who forges a strong romantic bond with Chloe Sevigny’s would-be singer Lana Tisdel and finds his own little Lone Star oasis before things go bad. Peirce doesn’t try to soft-peddle what happened to Teena the night that he was assaulted and killed, but she’s making the opposite of a true-crime tragedy. That’s ultimately the power of Boys Don’t Cry — it’s as much a story about love as it is about hate. —D.F.

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. —R.S.

Once upon a time, three student filmmakers went into the Maryland woods in search of an urban legend. They never came back — but what they shot on their camcorders did. The breakout sensation of Sundance ’99 and the movie that kickstarted the modern found-footage-horror boom, directors Eduardo Sánchez and Daniel Myrick had been seeding the notion that this story was the real deal via a fake website for months leading up to its premiere. By the time it finally hit theaters in July of that year, the buzz had grown so loud about this purposefully amateurish chronicle of an investigative true-crime doc gone very, very wrong that the hoax-or-no-hoax question was almost beside the point — audiences were already turning this guerrilla mockumentary into one of the biggest indie-movie success stories of all time. The image of Heather Donahue crying “I’m so scared” while hovering above her camera was already being parodied a week after the movie opened. And the cryptic ending, in which all shaki-cam hell finally breaks loose, still creeps us the fuck out to this day. —D.F.

At the time, people wondered if Trey Parker and Matt Stone could successfully convert and sustain their hit Comedy Central cartoon South Park into a full feature-length movie. Bigger, Longer, & Uncut not only proved they could stretch the show’s gags to uproariously absurd lengths — it helped extend the legacy and pop cultural currency of the series by several decades and counting. Plus it’s a musical! No cultural product had ever crammed this much foul language into so little space, and arriving on the heels of Eminem’s Slim Shady LP, it seemed to herald a new era of jaw dropping, ear-scorching permissibility. These days, the most shocking thing about this movie is how watchable it still is. Songs like “Uncle Fucka” and “Blame Canada” remain genuinely lol-worthy, and while the hypocritical anti-censorship crusades that Parker and Stone lampoon here have gone the way of the V-chip, the comedic power of Cartman, Kyle, Stan, and Kenny remains eternal. The corporate powers that be thought they were getting one last cash-in on a hit show that they were sure would be here-and-gone soon enough. Instead, they got a stone-cold classic. —J.D.

Most people knew Mike Leigh as a poet of Britain’s everyday people, chronicling the trials and triumphs of the working and middle class without ever really going full kitchen-sink-miserablist. So the idea that the filmmaker would turn around and suddenly mount an extravagant biopic about W.S. Gilbert and Arthur Sullivan creating their 1885 opera The Mikado surprised more than a few folks at the time. Yet it was immediately recognized as one of his best works to date when it premiered late in 1999, and it’s only gotten better as the years have passed. As played by Jim Broadbent and Allan Corduner, his Gilbert and Sullivan are cranky, mercurial, often weak and, when their long-term partnership hits the rocks, passive-aggressive to a fault. Yet they’re artists first and foremost, and when inspiration strikes after Gilbert visits an exhibition of Japanese culture, you can feel the two men feeding off each other’s talent in the most mutually beneficial of ways. Even if this wasn’t filled with members of Leigh’s usual rep company — Broadbent, Timothy Spall, Lesley Manville, Alison Steadman, Shirley Henderson, Katrin Cartridge — you’d recognize this as a valentine to both performers and those who give them a stage on which to rage. “I decided that it would be good to make a film about what we do, what we all go through,” he said, in reference to those who create for a living. Mission accomplished, sir. —D.F.

Stanley Kubrick’s final film was more than a decade in the making — and who knew that the master of painting humanity in bleak terms would come up with such a slyly funny look at love and marriage, which too rarely have much to do with one another? Tom Cruise cannily played against type as Bill, a cocky Manhattan doctor who finds out just how little he knows about relationships, sex or the stirrings of the human heart. Provoking his metaphysical nocturnal journey across the city — Is it all in his imagination? Does it matter? — is a shocking confession of a near-infidelity by his wife Alice, portrayed by Cruise’s real-life spouse Nicole Kidman. Many went to Eyes Wide Shut to watch its married-couple stars, hoping to obtain a glimpse into their high-profile relationship. Instead, they got what might be Kubrick’s most personal statement. Wed to third wife Christiane for 40 years before his passing, he was an unerringly faithful family man — the dismay he had for the human race was at odds with the great love he experienced at home. And yet Eyes Wide Shut laid bare the fear and desire that lingers in even the happiest couplings. Now a Yuletide staple, his swan song fashions a unique perspective on that beloved, fraught holiday, arguing that we should spend it with those closest to us — even if they have secrets we may be better off never knowing. —T.G.

From the same Sundance that gave us a horror movie you might mistake for a documentary (see No. 18 on this very list) came a documentary you might mistake for a fictional comedy. Not that any screenwriter could have invented Mark Borchardt, the hapless horror buff and stubbornly persistent Wisconsin filmmaker at the center of this cult sensation. Some have accused director Chris Smith of poking fun at his subject, whose quixotic quest to finish a low-budget occult potboiler becomes a sometimes farcical tug-of-war between ambition and competence (or lack thereof). But the film is more of a Rorschach test, challenging the limits of an audience’s belief in creative pursuit. If you have any affection for the indefatigable spirit of this Midwest answer to Ed Wood — to say nothing of the vividly captured America of the title — it will be mirrored right back at you. And few films, nonfiction or otherwise, have better captured the Sisphyean task of making a movie with little more than gumption to your name. —A.A.D.

David O. Russell’s first two movies, Spanking the Monkey and Flirting With Disaster, suggested an impish, talented indie filmmaker who relished coloring outside the lines of established genres. With Russell’s third picture, however his ambitions exploded. Set during the waning days of the Gulf War in early 1991, Three Kings captured the insanity of combat — and the stupidity of the United States’ gung-ho foreign policy — by finding the dark humor in a group of macho U.S. soldiers (George Clooney, Mark Wahlberg, Ice Cube and Spike Jonze) looking for ill-gotten gold, only to wind up in a world of hurt. Clooney and Russell famously clashed on set — this summer, the Oscar-winning actor referred to the director as a “miserable fuck” — and even decades later, one can feel the film’s chaotic tension, the sense that this modern-day Treasure of the Sierra Madre could go careening out of control. And yet, that coiled insanity only makes this semi-satirical war movie all the more gripping. When the film hit theaters, the Gulf War seemed like ancient history after two terms of Bill Clinton, but the horror of 9/11 was just two years away — and, then soon after, America would return to Iraq, having learned nothing. Russell was looking back in anger, never realizing he also was foretelling the future. —T.G.

Envy those who went into M. Night Shyamalan’s spooky phenomenon unaware. The same word-of-mouth that drove people to this summer sleeper also let its big secret slip. Not that it was really possible to spoil the movie: The real twist is how much it transcends its legendary final minutes, which pull the rug out from under what’s otherwise a startlingly elegant supernatural drama about disconnection, loneliness, and purpose. Rare is the blockbuster with performances as sensitive as those delivered by an unusually reserved Bruce Willis and a young, Oscar-nominated Haley Joel Osment, playing an adolescent clairvoyant haunted by his gift. And for as much as Shyamalan nurtures his inner Rod Serling, he also exhibits the other major hallmark of the divisive career to come: a careful, classical sense of craft that once caught him comparisons to Hitchcock and Spielberg. —A.A.D.

Everyone was scrambling chronology in the post-Pulp Fiction indie-movie landscape of the late ’90s, but few did so as purposefully, seductively, aand stylishly as Steven Soderbergh. Following his nonlinear Elmore Leonard adaptation Out of Sight, the director returned to elliptically fracture the fish-out-of-water story of an English thief (Terence Stamp, ferocious and heartbreaking) who travels to Los Angeles to get to the bottom of his daughter’s death. The screenwriter, Lem Dobbs, famously took umbrage with how Soderbergh chopped up and rearranged his script, leading to one of the liveliest and most contentious commentary tracks in DVD history. But the ruthless elisions are the key to the movie’s tremendous power; they transform a simple, gritty revenge yarn into something more psychologically rich, placing us inside the mind, memories, and regrets of Stamp’s bereaved force of vengeance. Soderbergh’s coolest trick: repurposing footage of the actor from an old movie, Poor Cow, as subliminal visions of his youth. —A.A.D

Remember how we mentioned there was one exception to the qualification rule? It’s this one — Wes Anderson’s sophomore feature technically had a brief run at the tail end of 1998. But it didn’t go wide until February 19th of 1999, and there are few films that better exemplify the spirit of this maverick, gamechanging year than this one. Anderson’s second movie dropped on a world that had missed his debut film, the underdog Texas heist flick Bottle Rocket (1996). And all people knew about co-writer Owen Wilson was that he was one of the first to die in Anaconda. So Rushmore came as a shock, presenting a fully-formed sensibility — it’s really the first movie in which the director became Wes Anderson, American auteur and lover of fetishistically organized pop-cultural bric-a-brac. Jason Schwartzman broke out as Max Fischer, an eccentric prep-school playwright who forms strange friendships with businessman Bill Murray and widowed teacher Olivia Williams. Still in his 20s, Anderson turned this affectionate, bittersweet dramedy into a trailer for his entire future career, complete with a soundtrack full of British Invasion deep cuts by the Kinks, the Creation, and the Stones. That final scene is a tearjerker: some of the year’s most miserable movie characters dancing to the Faces’ “Ooh La La.” As for Murray, his umpteenth comeback attempt turned out to be the charm — he started over as an arthouse king. —R.S.

“I want you to hit me, as hard as you can…” Yes, we know, the first rule about Fight Club is not to talk about Fight Club, etc. — but you can’t discuss the Class of ’99 without singling out David Fincher’s twisted, visceral take on Chuck Palahniuk’s novel, in which a group of emasculated dudes find existential bliss at the end of a bloody fist and then funnel their energies into tearing it all down. (Thankfully, society was never, ever bothered by angry groups of bros again. The end.) And like the best of the year’s movies, this sick joke of a satire feels both completely of its time yet still timely as hell, not to mention eerily prescient. Brad Pitt’s Tyler Durden remains the poster boy for alpha-male anarchy, Edward Norton’s self-harming everyman continues to resonate with anyone who’s felt alienated by modern consumerist culture, and the Pixies’ “Where Is My Mind?” will always be the soundtrack cut that allows the film to go out not on a whimper but a bang. Look at Fight Club, and you see a glorious bygone moment in American filmmaking, before the superheroes took over. You also see the present, however, and, God help us, the future. —D.F.

David Lynch spent most of the decade giving us some of the most unsettling, surreal visions of a world steeped in sex, violence, and sheer weirdness. And then, in 1999, he made a Disney movie. It might have been the oddest fit of director and studio in modern history, and while The Straight Story is maybe Lynch’s most quote-unquote normal movie, that doesn’t make it any less spectacular than his more outwardly experimental work. Based on the real life story of Alvin Straight, a man who road a lawnmower from his home in Iowa to Wisconsin to visit his estranged brother, The Straight Story this gentlest of films was a passion project of Lynch’s frequent editor Mary Sweeney, who wrote the script along with John Roach. To play the 73-year-old in failing health who makes this slow journey, Lynch cast Richard Farnsworth, who brings a stoic grace to Alvin’s determination. The saga is episodic: Along the way Alvin meets a variety of different people, including a young pregnant woman who has run away from home and a group of bicyclists who ask him about getting old, to which he replies, “The worst part of being old is remembering when you was young.” It’s a sweeping piece of Americana, and a vision of the country that is rooted in connection, with Farnsworth’s empathetic portrayal of Alvin at its core. —E.Z.

Pick Flick! Alexander Payne’s scathing take on Tom Perrotta’s novel starts off as a revenge movie: Matthew Broderick’s likable midwestern version of Mr. Chips is angry that his fellow educator got deservedly busted and ousted for having an affair with Reese Witherspoon’s underage Tracy Flick. Punishment, in his eyes, is denying this hyperambitious senior her “destiny” in becoming the student body president, which is why he enlists Chris Klein’s hunky, dimbulb football hero to run against her. Soon, a third-party candidate enters the race, running on a platform of “Nothing matters, sheeple!” — and then the shit really hits the fan. More than a few folks would late make the comparison between the movie’s blond, female striver and a certain 2016 presidential candidate; more than a few folks have also stopped to wonder why, in 1999, most assumed Flick was the movie’s de facto villain. In the decades since Payne’s peerless political satire hit screens, it’s jabs at petty grudges that metastasize into scandals, contested election results, curdled entitlement and nihilism as a populist ideology have only cut more to the bone. Twenty-five years ago, Election was a surefire winner for being one of the best movie of a perversely great year for American moviemaking. Now it seems way too prescient for comfort. —D.F.

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’ maneuvers 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. —D.F.

As soon as audiences caught wind of the first frames of Sofia Coppola’s still sensational debut feature—images of a languid suburban summer punctured by violence—it was clear she should not be written off as a lesser scion to her father, Francis. Her personal vision flows through this adaptation of Jeffrey Eugenides’ novel of the same name, melding fantasy with melancholy as she tells the story of the five Lisbon sisters, the beautiful blondes siblings who all meet tragic ends. They can be almost heavenly—that indelible portrait of Kirsten Dunst’s Lux Lisbon, overlaid in the sky against perfect clouds! — but movie also captures the grim realities of their suicides, and the oppressive ways in which their parents (played by Kathleen Turner and James Woods) refuse to acknowledge the depression that haunts their family. While The Virgin Suicides launched Coppola’s career, it also marked the start of her fruitful collaboration with Dunst, who embodies the themes that would preoccupy Coppola’s career: the pain and pleasure of being a teenage girl. Her smile is intoxicating, but so is the sadness in her eyes. —E.Z.

Michael Mann has made more popular films, more financially successful films, more technically groundbreaking films and more quotable films than this drama about Jeffrey Wigand, a former executive who helped expose Big Tobacco, and Lowell Bergman, the 60 Minutes producer who fought tooth and nail to broadcast his story. But pound for proverbial pound, there may not be a better Michael Mann movie than The Insider, and the way in which the director, working from an absolute banger of a script by Eric Roth, turns this talky drama into an airtight, tense thriller without sacrificing an ounce of gravitas is still astounding to this day. It’s a tale of not one but two whistleblowers, both of whom find themselves at the mercy of their corporate overlords: For Wigand, it’s the businessmen making polite threats and sending goons to harass his family; and for Bergman, it’s the network bigwigs at CBS, who fear being mired in lawsuits if their news division runs this story in full. Each of them have their share of issues. But each of them are willing to risk it all to get the truth out there.And while you expect the usual across-the-board great performances — Mann has always been a first-rate director of actors — there’s a reason that people continue to single out Russell Crowe and Al Pacino’s work here. The future Gladiator star is a twitchy, anxious mess, playing a family man coming apart at the seams who’s likely to pull the plug on the whole endeavor; it’s one of the more nuanced turns in this particular run of his career. And Pacino makes good use of his dynamic range here, keeping things Corleone-like calm one second and going Full Shouty Al the next. (Regarding Christopher Plummer’s volatile Mike Wallace, the fact that he didn’t get nominated for an Oscar for this is a crime.) Mann has always talked about his fascination with professionals who not only do their jobs well but display god-level grace under pressure. In telling the story of two men battling against the tide, he himself has lived up to that code. It’s the All the President’s Men of broadcast-journalism movies. —D.F.

A depressed puppeteer hatches a scheme to cheat on his wife with a coworker. He ends up discovering a portal straight into the mind of… John Malkovich. It’s plenty wild that such an outrageous premise made it to movie screens completely intact, with a $10 million budget and a cast of Hollywood actors like John Cusack, Cameron Diaz, and Catherine Keener game to play unhappy, unflattering neurotics. What’s wilder still is that the logline doesn’t begin to convey the full, deranged genius of this metaphysical tragicomedy from the mad screenwriter Charlie Kaufman and the music-video visionary Spike Jonze, both making their feature debuts. You think the premise sounds out there, and then you get to the sequence shot from the POV of a traumatized chimpanzee. Or the one where Malkovich climbs through the portal himself and ends up experiencing a hilariously nightmarish feedback loop of his own consciousness, a look at life through the Malkovich filter.Over the years since, the idea of stepping into someone’s mind has come to look like a handy metaphor for Kaufman’s whole career — the way every one of the movies he’s written and/or directed has functioned like a peek into his warped imagination. Of course, this gonzo meditation on desire, creation, and identity isn’t the brainchild of just one brainiac. It also announced Jonze as an impish new maverick of American fantasy, a filmmaker with one foot planted in scraggly bohemian reality and the other in a dazzling surrealism. His casually virtuosic staging keeps the whole crazed enterprise afloat, even as Kaufman’s dark insecurities drag it down. With Being John Malkovich, the two emerged together, fully formed. The very existence of the movie practically refutes the pessimism it expresses: While their characters rattled the cages of their own personal prisons, Kaufman and Jonze found freedom in rare, uncompromised Hollywood expression. —A.A.D.

It’s no great exaggeration to say that Hollywood action cinema can be divided into two eras: before and after Neo. If anything, that binary downplays the seismic impact of this landmark cyberthriller blockbuster, which hit movie screens like a helicopter kissing the glass surface of a skyscraper and sending ripples in every direction. The Wachowskis, coming off the success of their brilliant neo-noir Bound (the best erotic thriller of them all, by the way), found the future in the past. Their vision of a world plugged unwillingly into a shiny, digital mirage borrowed freely from other movies, connecting the wire-fu of Tsui Hark, the bullet opera of John Woo, and the technophobic doomsaying of James Cameron like clusters of code. But the result was so stylishly, inventively synthesized that it created a new model of popcorn entertainment, as dedicated to its dorm-room philosophy as it was to the lizard-brain spectacle of Keanu Reeves defying the laws of gravity and motion.Twenty five years ago, everyone knew the movie would revolutionize special effects. But its aftershocks have reached much further than bullet time. Reeves achieved an action-hero immortality, becoming the perfect vessel for ongoing exercises in East-meets-West martial-arts glory, like John Wick and its pretenders. And the film’s depiction of life as a computer program took on symbolic heft, with the red pill hijacked by misogynistic memelords before Lana and Lilly set the record straight, reclaiming Morpheus’ truth capsule as a moving metaphor for gender dysphoria. Hell, even the proliferation of simulation theory owes a debt to the ideas the Wachowskis send pinging across multiplex screens. Ultimately, the larger power of their premise lies in how it got people thinking about the nature of reality itself. In that respect, The Matrix rewired minds as well as movies. Whoa indeed. —A.A.D

Near the end of the press tour for Boogie Nights, Paul Thomas Anderson decided he wanted to jump into making another movie right away — the 26-year-old writer-director was scared that his breakthrough film had set the bar high in terms of people’s expectations, “and I thought I could cut them off at the pass.” The idea was to make something closer to his 1996 debut movie, Hard Eight; it would be small, modest, and the sort of run-and-gun production that characterized the Indiewood touchstones from the beginning of the decade rather than the end of it. Just shoot something quickly, with friends and maybe one or two members of his usual repertory company. Nothing too big or dramatic.What Anderson came up with instead was a sprawling, multi-character ensemble piece that follows a group of Angelenos, each in a state of respective reckoning and crisis. It has close to dozen main characters and a once-in-a-lifetime cast (Jason Robards, John C. Reilly, Julianne “Shutthefuckup” Moore, Phillip Baker Hall, Phillip Seymour Hoffman, William H. Macy, Melinda Dillon, Melora Walters and Tom Cruise — who should have won the Oscar). The constantly moving camera and cross-cutting between narratives, combined with Jon Brion’s melodic yet menacing score, kept the tone pitched at the heightened levels of an opera. And that’s before Anderson drops in an actual aria from an opera. And choreographs a music video featuring his actors singing Aimee Mann’s “Save Me.” And unleashes a biblical plague of frogs on the San Fernando Valley.More than anything else released during this annus mirabilis of American moviemaking, Magnolia exemplifies everything that made the class of ’99 so memorable. It was gloriously messy, magnificently obsessive and excessive, and wore its emotions not just on its sleeve but its whole jacket. His attempt to weave disparate threads into a tapestry depicting society having a collective nervous breakdown — asked by the studio head about balancing six storylines, Anderson corrected him by saying, “I’m trying to make one story” — was still expansive enough to encompass love, death, loneliness, trauma, addiction, forgiveness, magical realism, game shows and toxic masculinity before it had a name. PTA not only proved that he wasn’t just a two-and-done wonder, but made a strong case for being his generation’s Robert Altman. (And he was just getting warmed up.) There was no shortage of ambition on display among filmmakers in 1999, but this empathetic look at people clawing their way out of self-dug holes remains the year’s high point of following an artistic vision no matter what, and achieving something perilously close to perfection. —D.F.