The 99 Best Movies of 1999, Ranked

After the success of his 1994 low-budget hit Clerks and its more mainstream follow-ups Mallrats and Chasing Amy, slacker wonderkind Kevin Smith attempted this ambitious riff on Catholicism, which was deemed to be “polluted” by the American Society for the Defense of Tradition, Family and Property. The film’s Weimer Nineties casting is cute: Ben Affleck and Matt Damon are fallen angels trying to exploit a Papal loophole to get back into heaven; Chris Rock is a Black apostle written out of the Bible because of racism, Salma Hayek is a celestial muse turned earthbound stripper; George Carlin drops by as a New Jersey bishop trying to give the Church a cool new image; and Alanis Morrissette appears as God. By mish-mashing references to Star Wars, The Piano, and Home Alone in with its riffs on stuff like the Virgin Birth, Sodom and Gomorrah, and plenary indulgences, the movie also genuinely reflected the experience of Catholic kids raised in the Seventies and Eighties who’d transmogrified their ambivalence towards of the faith of their upbringing into an equally iconic embrace of a new moral system – the Church of Pop Culture. Today, we might call Smith’s attitude “lol something matters.” —Jon Dolan

You can understand why writer-director Troy Duffy’s crime thriller helped signal the end of a certain type of tough-guy movie that plagued the decade — even by the ’90s indie-filmmaker-watches-first-two-Tarantino-movies-too-many-times standards, the abundance of self-conscious flourishes, proto-edgelord offensiveness and performances for which “bad” is too kind a descriptive is a lot to take. But you also get why this film still has a cult following, especially once the Irish-American MacManus brothers (played by Sean Patrick Flannery and future Walking Dead MVP Norman Reedus) decide to go from South Boston ruffians to full-on vigilantes, one hail-mary at a time. Plus it has one of Willm Dafoe’s more gloriously eccentric performances, and considering we’re talking about this guy, that’s saying something. —David Fear

In West Canaan, Texas, they worship God, guns and the gridiron state champions known as the West Canaan Coyotes — just not in that order. In this community, star quarterback Lance Harbor (Paul Walker) is considered the second coming of Roger Staubach, and whatever Coach Bud Kilmer (Jon Voight) says is akin to gospel. As for the team’s second-string QB, Jonathan Moxon (James Van Der Beek), he’s content to warm the bench and read the paperback of Slaughterhouse Five he has stashed in his playbook. Then Harbor gets hurt, Moxon has to sub in, and he discovers firsthand the agonies and ecstasies of end-zone heroism. Director Brian Robbins’ fan favorite is best remembered today for its jock-jam soundtrack, the late Ron Lester’s performance as offensive guard/good ol’ boy Billy Bob, and extolling the seductive virtues of “whip-cream bikinis.” In terms of portraying high-school football’s cultural hold on Lone Star small towns, it isn’t fit to hold Friday Night Lights’ jockstrap. But it does give you a Hall-of-Fame sports movie villain in the form of Voight’s monomaniacal coach, whose tyranny on and off the field is truly terrifying. —D.F.

It may not reach the cinematic heights of his early classics Billy Madison and Happy Gilmore, but Adam Sandler’s contribution to the Class of ’99 features all the regular Sandler Players (Steve Buscemi as a bum, Rob Schneider as a delivery-man buddy) and hits all the reliable beats. To wit: Kinda-loser-with-heart-of-gold Sonny Koufax hatches a scheme to impress a pretty, accomplished woman, which involves cavorting around Manhattan with an “adopted” five-year-old son (played by twins Cole and Dylan Sprouse). While teaching the kid the joys of pissing on public buildings and tripping passing rollerbladers, Sonny ends up falling for a different very pretty, very accomplished woman — in this case, Nineties staple Joey Lauren Adams. Yes, the film’s attitude about the fairly random gay couple Sonny hangs with, while progressive-seeming at the time, reads much less so today. And yes, Sonny’s obsession with his friend’s fiancée (Leslie Mann) having waitressed at Hooters feels, dare we say, slightly misogynistic. But even at his knowingly frattiest, Sandler is nothing less than endearing. —Maria Fontoura

Wes Craven took a break from his master-of-horror duties to helm this based-on-a-true-story melodrama about Roberta Guaspari, a single mother who gets a job teaching the violin to kids in East Harlem. Everyone from her fellow teachers to the students’ parents are skeptical of what appears to be another stranger with a savior complex, until Guaspari ends up empowering these young musicians; when the successful program is later in jeopardy thanks to citywide budget cuts, a host of real-life virtuosos come to the rescue. After Scream became a hit, Craven leveraged his industry currency to convince his Miramax patrons he was the right man to bring this to the screen. The result feels like a lot of the other semi-schmaltzy the studio put out in the late 1990s, though it helps that Meryl Streep is playing Guaspari, and that everyone from Angela Bassett to Cloris Leachman to Gloria Estefan is filling out the supporting cast bench. —D.F.

Frank McCourt’s harrowing memoir of an Irish childhood characterized by poverty, hardship and tragedy got the prestige-lit event-movie treatment — it was released on Christmas Day in 1999 — and while it didn’t have quite the impact that the bestselling book did, it still left audiences dazed and reeling. No one would ever accuse Alan Parker (Midnight Express, Angel Heart, Pink Floyd: The Wall) of being subtle, and the director treats the squalor and the familial strife like he’s directing a war movie. What keeps this from devolving into standard poverty porn are the performances, notably Emily Watson as Frank’s long-suffering Ma; Robert Carlyle as his well-meaning drunk of a dad; Joe Breen as the young Frank (a literal poster boy, given that it’s his face peering out from a stark, black-and-white picture in the film’s marketing image); and Michael Legge as the teenage Frank, who manages to write his way out of hell and into heaven, i.e. the Statue of Liberty’s home. —D.F.

It will forever be known as the 007 movie starring Denise Richards as an American nuclear physicist named Christmas Jones. [Feel free to add your own snarky comment here.] Yet the 19th James Bond films, the third to star Pierce Brosnan, and the last time the MI6 agent was licensed to kill in the 20th century has its moments, including a riff on The Spy Who Loved Me‘s ski chase and Brosnan being both straddled and strangled by top-notch femme fatale Sophie Marceau. Throw in Robert Carlyle’s Renaud, a chilling variation on the unfeeling Bond villain in that he literally has lost his sense of touch, Robbie Coltrane reprising his Goldeneye Russian mobster and the longest pre-credits sequence in the series’ history, and it’s enough to make you forget the franchise was in danger of running in fumes. (You know this is a very much a late ’90s entry as well, given that Goldie plays a henchman and you can hear turntablist scratching added to John Berry’s theme music.) Brosnan would play Bond one more time, in 2002’s Die Another Day, before ceding the role to the actor who’d recast the iconic character for the 21st century. —D.F.

You can’t overstate the cultural saturation of Austin Powers in the late Nineties — he shagged the zeitgeist, baby! Mike Myers and Jay Roach created a global obsession with the Swinging London spy who got frozen in 1967, then defrosted to battle his nemesis, Dr. Evil. The original 1997 Austin Powers: International Man of Mystery was a comedy polished with love and finesse, and while the summer-of-’99 sequel was an obvious bash-it-out quickie, it was still popcorn-pukingly funny. You got Myers once again doing double duty; Heather Graham as CIA agent Felicity Shagwell; Verne Troyer as Mini-Me; a music interlude from Burt Bacharach and Elvis Costello, a lunar base divided into Moon Unit Alpha and Moon Unit Zappa; Madonna’s “Beautiful Stranger”; and the Russian assassin Ivana Humpalot. The third Powers entry may have sunk the franchise, but this second one kept the grooviness factor on 10. —Rob Sheffield

A.K.A. the movie in which a pre-Iron Man Robert Downey Jr. gets slapped by Mike Tyson — and that’s maybe the fifth or sixth wildest thing that happens in writer/director/accused sexual predator James Toback‘s satire on race, celebrity, and cultural appropriation. Brooke Shields is a documentary filmmaker making a movie about the impact of Black culture on white teens; Ben Stiller is a corrupt cop trying to get a basketball player (portrayed by New York Knicks’ Allan Houston) to throw a game; everyone from Claudia Schiffer to members of the Wu Tang Clan show up at one point another and improvise scenes. It’s the sort of film that opens with an explicit interracial threesome in Central Park and only gets more messy, outrageous and provocative from there. It’s unforgettable, at the very least. —D.F.

A 17th-century Italian violinmaker believes he has finally crafted the perfect instrument — then tragedy strikes, and after varnishing it in a blood-red hue, he demands this cursed item be stricken from his sight. Over the next few centuries, the violin will change hands a number of times, and end up affecting the lives of German child prodigy, a British wastrel, a Chinese apparatchik and an American appraiser (Samuel L. Jackson) who becomes obsessed with this legendary instrument when it comes up for auction. This multinational production from French-Canadian filmmaker François Girard (Thirty-Two Short Films About Glenn Gould) is a good example of the extravagant, globetrotting costume dramas that filled arthouses throughout the decade, and gives Jackson a nice chance to play against type. —D.F.

“I killed the teen dream. Deal with it.” With these gentle words, Rose McGowan takes her place in history as the teen-movie villain-queen canon. McGowan, Julie Benz, and Rebecca Gayheart play a trio of mean girls who rule the halls of Reagan High, until they accidentally snuff a rival with a piece of candy. It was arguably the darkest teen comedy since Heathers — and it remains one of the funniest. Writer/director Darren Stein made this a nonstop barrage of Wildean bitch-quips (“I don’t believe we’ve met, what with the cruel politics of high school and all”) and Nineties fashion. Plus it’s got a hell of a soundtrack, too, with the Donnas rocking the prom. McGowan chews up her “Satan in heels” role, especially when she orders her minions, “You are gonna walk into that school and strut your shit down that hallway like everything is peachy fucking keen!” —R.S.

Martin Scorsese reunited with his Taxi Driver screenwriter Paul Schrader for yet another nocturnal tour through the mean streets of New York City, and this time God’s Lonely Man isn’t a cabbie but a paramedic, perpetually working the graveyard shift and perilously perched on the edge of sanity. As played by somewhat restrained (for him) Nicholas Cage, this burnt-out EMT keeps hallucinating the ghost of a young woman he couldn’t keep from flatlining and getting paired with a series of increasingly more unstable partners. Salvation comes in the form of Mary (Patricia Arquette), who our hero meets during a call involving her father, but even she can’t totally save his soul. The closest thing to God in this world is a dispatch operator who keeps sending them through Gotham’s seven circles of hell, and is blessed with the voice of Scorsese himself. It’s a flawed movie, to be sure, yet it’s still proof that even the auteur’s minor works can still be wild rides. —D.F.

To say that time has not been kind to the Best Picture Oscar-winner of 1999 would be the understatement of the year — and that notion still applies even if you don’t factor what’s happened regarding the movie’s lead actor in the past seven years. Sam Mendes’ satirical look at the “perfect” American family was considered a significant statement on the fragile, fractured mindset of the paterfamilias at the end of the American century, and while you wouldn’t call Lester Burnham’s midlife crisis aspirational, the movie definitely treats regression back to his teen self as something like suburban liberation. The shot of a plastic bag whirling in circles, courtesy of Wes Bentley’s boy-next-door videographer, is no longer a shorthand for existential ennui or finding the finding the beauty in the mundane; the movie’s signature image of a teenage cheerleader naked under roses, however, has become twice as icky. Even at the time, the idea that this was the standout movie of a standout filmmaking year felt questionable. Yet it still went home with five Oscars, so…. —D.F.

The MCU was not even a glint in Kevin Feige’s eye when this parody of superhero teams — sprung directly from the pages of Bob Burden’s Flaming Carrot Comics — hit screens in the middle of ’99. (For context: The first X-Men movie was still a year away from being released.) When the beloved do-gooder Captain Amazing (Greg Kinnear) is kidnapped by his nemesis Casanova Frankenstein (Geoffrey Rush), Champion City suddenly finds itself without its main champion. For such Grade-Z superheroes as Mr. Furious (Ben Stiller), the Blue Raja (Hank Azaria) and the Shoveler (William Macy), however, this is finally the opportunity to prove they belong in the big leagues. Quicker than you can “Avengers Assemble!”, they’ve recruited a handful of equally ambitious also-rans under the moniker “Mystery Men” — such as Invisible Boy (Kel Mitchell), the Bowler (Janeane Garafalo) and Spleen (Paul Reubens), whose superpower is toxic flatulence — and try to save the day. At the dawn of the new millennia, this was a mildly funny comedy with a handful of alt-comedy and A-list talent. Now, in an age when every third-tier Marvel group gets their own franchise, it’s a hundred times more hilarious. —D.F.

Walter (Robert De Niro), a bigoted retiree who suffers a stroke, must learn to regain his speech by seeing a singing coach, a transgender woman named Rusty (Philip Seymour Hoffman). The odd-couple pairing, was one of the first Hollywood movies to focus on trans characters, a community that filmmaker Joel Schumacher had observed firsthand. (“The people that inhabit Flawless are very real for me,” the writer-director said. “Schumacher, “These are interesting communities and people pass them by without even noticing them.”) With modern eyes, we can see how this film would be made differently today — for instance, a trans actor would play Rusty, although Hoffman’s performance is exceedingly lovely and nuanced, eschewing stereotypes. Nonetheless, the movie stands as a bold step into a world that, to that point, mainstream American cinema had been too timid to touch. —Tim Grierson

Spike Lee returns to the long, hot New York summer of 1977, when a serial killer known as “the Son of Sam” had everyone in the five boroughs on edge. If you’ve read Jonathan Mahler’s invaluable history Ladies and Gentlemen, the Bronx Is Burning, then you know this was a crazy year, from the Yankees’ Reggie Jackson breaking records to looters breaking shop windows during an epic blackout. For Lee and his cowriters Victor Colicchio and a pre-Sopranos Michael Imperioli, all that terror and chaos was mostly a good excuse to dive into cultural divides and the neighborhood tribalism that’s still part of NYC’s DNA. It’s a bit of a spirit-of-’77 hodgepodge, complete with disco and punk scenes, a Plato’s Retreat interlude, and the era’s paranoia dialed up to 11, along with a straight-outta-early-Scorsese storyline in which John Leguizamo’s nice Catholic hairdresser struggles with a serious Madonna v. Whore complex. Both the camerawork by Ellen Kuras and the acting — notably Adrien Brody as a part-time male hustler and full-time CBGB’s habitue, and Mira Sorvino and Jennifer Esposito as two Brooklynites navigating respectively rocky relationship terrain — keep this from devolving into late ’70s cosplay. —D.F.

Many were thrown by the fact that David Mamet, the poet of the four-letter word, would be interested in something as genteel as Terence Rattigan’s play, set in upper-crust England in the 1910s. But at heart, Mamet has always cared about ethics and behavior — why we’re drawn to do the things that we do — and so it was no surprise that his adaptation would focus on moral codes and the sinister strictures of social mores. Sir Robert Morton (Jeremy Northam) is a renowned defense attorney hired to represent Ronnie Winslow (Guy Edwards), a teenage naval cadet accused of stealing a postal note, resulting in his expulsion. This is no simple courtroom drama, however, with Mamet equally focusing on how the trial affects the Winslow family — in particular, the boy’s prideful father (Nigel Hawthorne), who risks his reputation on the word of his son. Nobody drops a F-bomb, but the man behind Glengarry Glen Ross and The Spanish Prisoner remains fixated on duplicity, self-deception, and how the people around us are far more unknowable than we could possibly grasp. —T.G.

Celebrated author John Irving adapted his own bestselling novel, which tells the story of Homer Wells (Tobey Maguire), who grows up in an orphanage in Maine. The doctor who runs the home, Wilbur Larch (Michael Caine), also performs secret abortions, and trains young Homer, a reluctant pupil, in obstetrics. After Charlize Theron’s Candy shows up (on the arm of Paul Rudd, in a rare dramatic role as a World War II fighter pilot) in need of Larch’s services, Homer is suddenly inspired to leave the orphanage and experience life — which includes apple-picking (for work), fornicating with Candy (for pleasure), and uncovering dark family secrets about his fellow pickers that compel him to use his ill-begotten doctoring skills. Directed by Lasse Hallström, the film won Irving a screenplay Oscar as well as a second Best Supporting Actor statuette for Michael Caine. But its most lasting contribution to the culture may be Larch’s ritual bedtime farewell to his charges. Say it with us now: Good night, you princes of Maine, you kings of New England. —M.F.

A frustrated writer (Jeremy Theobald) begins pathologically stalking random strangers on the streets of London, partially out of a need for inspiration and partially out of boredom. One of his marks turns out to be a thrill-seeking thief named Cobb (Alex Haw), who is less interested in stealing things for profit than the perverse glee of disrupting people’s lives. Soon, the stalker is recruited to join as a partner in crime. Then he spies one of their victims in a bar — a sultry blonde (Lucy Russell) — and decides on a whim to approach her. Nothing is ever quite what it seems here, however. Made on a shoestring budget and shot in black & white, this modest, clever thriller played a few festivals and got a brief run in the spring of ’99. It might’ve been just another one of those come-and-go indie projects were it not for the fact that its first-time filmmaker, a 28-year-old named Christopher Nolan, was about to become one of the defining writer-directors of the 21st century. And when you watch this inside-out neo-noir now, you can see that so many of the thematic obsessions and stylistic tics associated with the Oscar-winner’s work were all there, right from the very beginning. —D.F.

Every screenwriter faces two great fears: losing their edge and losing their position in an industry that already treats them like lepers. Stephen Phillips, the sad-sack scribe at the center of writer-director-comic genius Albert Brooks’ comedy, happens to be dealing with both issues at once. Luckily, his best friend (Jeff Bridges) thinks he has the solution: work with a muse — it turns out they’re real! — who can help get his career back on track. Then Phillips meets this high-maintenance mythological woman played by Sharon Stone, and every aspect of his life is completely thrown into chaos. Brooks’ farce works better as a satire of Hollywood fickleness than a self-directed star vehicle for his neurotic persona (Martin Scorsese’s rant about remaking Raging Bull, “but with a thing guy… like, really thin!” remains a hilarious self-own, while the joke in which James Cameron is advised to “stay away from water” plays 20 times funnier post-Avatar sequel). To say Stone steals the movie suggests that Brooks didn’t hand this to her on a silver platter from the get-go; the divine-diva-run-amuck role feels tailor-made for her strengths as a comedian, and dear Zeus, does she ever make the most of it. —D.F.

It’s a scenario familiar to most of us: One minute, you’re making sweet, sweet love to your husband on your expensive boat, the next you’re waking up with his blood all over you, he’s nowhere to be found and the cops, unsurprisingly, have lots of questions. This revenge movie became one of the big surprise hits of 1999, and helped establish Ashley Judd as a name-above-the-title lead outside of the Indiewood world. Accused of murdering her spouse, her everywoman is sent to prison, only to discover that — spoiler alert! — her husband (Bruce Greenwood) faked his death and left her to take the fall. Thanks to the titular legal ruling, she can’t be convicted for the same murder twice, which clears the path for her to hunt him down and actually kill the rat bastard. Meanwhile, her parole officer Tommy Lee Jones, who has plenty of experience hunting down fugitives, is hot on her trail. Is it ridiculous? Of course! Is it also the sort of late ’90s star B movie that turns solid actors into A-list movie stars, and makes you miss when these kind of films were part of a well-balanced moviegoing diet? Also yes! —D.F.

Disney’s big animated movie of ’99 wasn’t a fairy tale, an ancient fable, or a princess-driven musical — instead, they opted for a tween-friendly take on Edgar Rice Burroughs’ famed king of the jungle. Raised by Glen Close’s motherly ape, the man-cub will grow up to sound like Tony Goldwyn, look like Eddie Vedder circa Ten and have the agility of Tony Hawk on a half-pipe. Everything’s hunky-dory until British explorers show up, complete with a hunter intent on bagging and selling the jungle’s simian residents. On the plus side, they’ve also brought a comely young lass named Jane (Minnie Driver) and, well, you know the rest. We may eventually forgive the soundtrack’s insipid Phil Collins’ song “You’ll Be in My Heart” for winning the Oscar over “Blame Canada!,” though that day won’t be today. But awards snafus aside, the Mouse House’s animation is particularly on-point, the set pieces move like gangbusters (see: this fight between Mama Ape and a leopard over Lil’ Tarzan) and Driver gives her heroine the perfect mix of wit, grit and romantic grace. —D.F.

It was the end-of-the-decade romp that set out to be a mash-up of every teen rom-com ever made—it’s practically a Now That’s What I Call High-School Prom Movies! sampler. But it’s pure charm, thanks to the power couple of Rachel Leigh Cook and Freddie Prinze Jr. It’s your basic Pygmalion-via-Breakfast Club makeover: Can the misfit art student turn into the prom queen just by taking off her glasses? Can the hero make a stupid bet but still win her heart at the end? Can you imagine a high school with Kieran Culkin, Paul Walker, Anna Paquin and Lil’ Kim? And most importantly, can Usher play the prom DJ who sends everyone home happy with “The Rockafeller Skank”? The answers are: Yes, yes, yes, and check it out now, the funk soul brother. She’s All That was the last movie Gene Siskel ever reviewed; he came through with his final thumbs-up. —R.S.

Jim Carrey went full Method-acting madness to play divisive comedian Andy Kaufman; he was so devoted to diving into the role that, in fact, that he drove everyone from his fellow cast members to director Milos Forman around him on set crazy. (Costar Danny DeVito looks like he’s ready to slug him at any moment.) The performance and the biopic remain remarkable, however, with one genius paying homage to another. Kaufman cannonballs from one outrageous subversion of celebrity niceties to another, from wrestling women to reading the entirety of The Great Gatsby to an audience in defiance of his club audiences. Few artist portraits are as playful or as combative, offering no middle ground for the viewer — you’re either on Kaufman’s (and Carrey’s) uncompromising wavelength or your sense of humor needs a tuneup. In a decade in which “selling out” was still considered a sin, Man on the Moon found hilarity and poignancy in an unapologetically joyous original insisting on being himself. —T.G.

The star of Bull Durham and Field of Dreams returns to the mound for one more affectionate ode to America’s pastime. You don’t need to know a splitter from a 98-mile-an-hour heater to appreciate the salty pathos Kevin Costner brings to Billy Chapel, an aging Detroit ace looking to close out his career with a perfect game — that is, if he can keep his mind from wandering to Kelly Preston’s dream-girl-who-got-away, introduced through flashbacks that lay out the bumpy course of their romance. Sam Raimi, the Evil Dead maverick calling the pitches, forgoes his usual demonic fastball in favor of a style as relaxed as a Sunday on the couch with a double header on the tube. It’s a right-down-the-middle Dad Movie — and a nice victory lap for an actor who always looks at home with his eyes on home plate. —A.A. Dowd