The 90 Best Movies of the 1990s

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What follows is a very unscientific gathering of the approximate collective opinions of our editors and film critics on the best movies of the 1990s. There are gaping holes, to be sure (even with a dozen nations on the list, foreign films are highly underrepresented, for instance). But we just couldn’t resist sharing with you some of the fun we had in reminiscing about one of our favorite decades in film history. Share your picks in the comments section below.

20. Boogie Nights (Paul Thomas Anderson, 1997)

Although Boogie Nights was Paul Thomas Anderson’s first epic production with an ensemble cast, time and perspective show it’s his closest brush with perfection. The auteur specializes in building up characters to break them down, and no one in his 1997 exploration of the pornography business is exempt from his deconstructive impulses. Few films are simultaneously hilarious and harrowing, and even fewer rely on dramatic irony for both effects. Boogie Nights is amusing because its characters are hapless, but it’s their ignorance that’s heartbreaking. What makes them real is their earnest desire to make a good product, even if they don’t know what constitutes quality. His fictional pornographers might have desperately and futilely clung to a time before video and amateur acting, but Anderson himself managed to put out a two-and-a-half hour film that is careful to never overstay its welcome—even when it asks for “one last thing.”—Allie Conti

19. Jackie Brown (Quentin Tarantino, 1997)

Jackie Brown is certainly the most underrated and possibly the best of all Tarantino’s films. Certainly it’s the most human and touching. Robert Forster’s gently wise performance alone elevates the film above its competition, and that’s before you even get to Robert DeNiro and Bridget Fonda, or to the force of nature that is Pam Grier. Plus the best soundtrack of any film of the ’90s (that’s right, I said it). Sure, the signature Tarantino craziness is there, and Samuel Jackson and Chris Tucker play it masterfully, but when Forster and Grier are alone in her house, you’re seeing something very different from QT—a real, true-life, grown-up film.—Michael Dunaway

18. Crumb (Terry Zwigoff, 1994)

It’s only fitting that an artist with as singular and “other” a vision as Robert Crumb would get a documentarian as daring as Terry Zwigoff, and a film as profoundly weird, disturbing, and entertaining as this one. Zwigoff explores not only Robert’s neuroses (and they are deep), but also those of his brothers and the entire family. And more importantly, it draws the lines between those neuroses and the artists’s often-infuriating personality and often-disturbing work. Possibly the best artist documentary of all time.—Michael Dunaway

17. Being John Malkovich (Spike Jonze, 1999)

From the genius, and honestly sort of insane, mind of Charlie Kaufman, the script for 1999’s Being John Malkovich is not only completely bizarre, it’s incredibly entertaining. When paired with director Spike Jonze, and boasting a start-studded cast, including John Cusack and Cameron Diaz, the idea of traveling through a portal literally into the mind of the real John Malkovich doesn’t seem quite as loony.—Nicole Oran

16. Sling Blade (Billy Bob Thornton, 1996)

I once read that in Greek mythic tragedy, once you understand the setup and the characters, everything that will happen in the drama is already determined. All that remains is for everything to play itself out. From very early on in the film, Sling Blade feels just that way. Everything that happens in the film must happen—could not do other than happen. And yet watching it unfold is a thing of beauty.—Michael Dunaway

15. Toy Story 2 (John Lasseter, Ash Brannon, Lee Unkrich, 1999)

This 1999 film cemented Pixar’s reputation as the studio for whom the phrase “the new Disney” might actually be an insult—to Pixar. (Disney itself solved that by buying Pixar for $7.4 billion or so in 2006.) As celebrated as Toy Story 2 is as a revelatory chapter in the Pixar Story, it’s easy to lose track of why it is deemed so. John Lasseter’s film is pitch-perfect from start to finish, with a plot that’s both intricate, heartfelt and structurally pristine. (This is especially jaw-dropping considering that the film was originally meant to be a straight-to-video sequel.) In a more just world, Toy Story 2 would have been nominated for more than just “Best Original Song” at the 2000 Academy Awards.—Michael Burgin

14. The Usual Suspects (Bryan Singer, 1995)

The movie is a cheat and a fraud. It’s as manipulative as it is dishonest, but unlike many other far lesser films worthy of the same description, all this flick’s shamelessness is on purpose. When it was released The Usual Suspects left viewers gob smacked, staring at screens with expressions matching Michael Caine and Steve Martin on the runway at the end of Dirty Rotten Scoundrels: at first confused, then maybe a little angry, but then ultimately delighted by how fooled they’d just been. Perfectly paced, brilliantly scored by director Bryan Singer and editor/composer John Ottman—the film never lets the marks know they’re being conned by the irresistible ensemble or Christopher McQuarrie’s dark, mischievous script. And then like that…it’s gone…—Bennett Webber

13. Dead Man Walking (Tim Robbins, 1995)

Any film that addresses one of the big, divisive issues of our day (abortion, immigration, homosexuality, etc.) runs the risk of being preachy. But the subject of this death-penalty film isn’t some wrongly accused saint. Sean Penn’s Matthew Poncelet is a murderer and the point of view of the victims’ family isn’t belittled. Still, the story’s herione, the nun played by Susan Sarandon finds empathy for all involved, and seeing that play out in all its cosmic difficulty is wonderfully redemptive.—Josh Jackson

12. The Big Lebowski (Joel Coen, 1998)

Jeff “The Dude” Lebowski has plenty of time on his hands—enough to while away the days chasing down a stolen rug, at least—but he can hardly get himself dressed in the morning, chugs White Russians like it’s his job (incidentally, he doesn’t have a real one) and hangs around with a bunch of emotionally unstable bowling enthusiasts. Any mission you set him off on seems bound to fail. And yet that’s the great joy, and the great triumph, of the Coen Brothers’ The Big Lebowski and its consummate slacker-hero. The Dude is a knight in rumpled PJ pants, a bathrobe his chainmail, a Ford Torino his white horse. Strikes and gutters, ups and downs, he takes life in ambling, unshaven stride—and more than dashing good looks and unparalleled strengths, isn’t that something we should all aspire to?

11. Fight Club (David Fincher, 1999)

There were many cult classics that emerged in the ’90s, but with perhaps the best performances from Brad Pitt and Edward Norton, Fight Club still stands out. Based on the Chuck Palahniuk novel, the characters start an underground fight club, which slowly but surely turns into the pure living hell of the narrator’s insomnia-induced insanity.—Nicole Oran