The 90 Best Movies of the 1990s

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80. Bound (The Wachowskis, 1996)
For me, that the Wachowskis did not continue to make films in this vein after their stunning debut is one of the great tragedies of late 20th-century cinema. This deliciously taut, witty, intense neo-noir is lean and mean, produced on a low-budget but dripping with high style—shot in color but heavy on blacks, whites and blood red. Gina Gershon is an ex-con who gets involved—in every sense of the word—with gangster Joe Pantoliano’s girlfriend, Jennifer Tilly and, even if you correctly predict that a degree of plotting, scheming and double-crossing soon follows, there is no way to fully describe how much fun it all is.—David J. Greenberg

79. The Battle Over Citizen Kane (Thomas Lennon, Michael Epstein, 1996)
If it’s not “the” story of the 20th Century, it’s certainly a story that embodies huge chunks of it. Alternating between the rise of media mogul William Randolph Hearst and the rise of dramatic wunderkind Orson Welles, the Oscar-nominated documentary presents an impressively even-handed picture of both men so that, when their colossal clash of enormous egos erupts, it’s hard to feel complete sympathy for either. The film depicts two passionate men—a power hungry tycoon and an artistic genius—driven by not always pure motives.—David J. Greenberg

78. Boys Don’t Cry (Kimberly Peirce, 1999)
The unforgettable true story of transgendered teen Brandon Teena unfolded before our eyes in this powerfully disturbing drama. Hilary Swank (as Brandon Teena) and Chloë Sevigny (as Lana, Brandon’s partner) created a love story that was star-crossed for sure, although viewers unfamiliar with the true story were wholly unprepared for a brutal, tragic ending. Swank took home the Oscar for a moving performance that, one could argue, rocked a generation to its core. It would not be a stretch to say that Boys Don’t Cry helped shape the ongoing conversation about the experiences of LGBTQ individuals in our society today; without the story of Brandon Teena, this conversation is incomplete.—Shannon M. Houston

77. The Wrong Trousers (Nick Park, 1993)
Aardman Animation first introduced the stop-motion comedy duo of addle-minded inventor Wallace and his smart, unspeaking canine Gromit in 1989’s genial “A Grand Day Out,” but the follow-up proved to be a classic of animated comedy. Director Nick Park brings a love of heist flicks and Alfred Hitchcock thrillers to this tale of a deadpan penguin who drives a wedge between man and dog as part of a nefarious plot that includes a robotic pair of pants and the most hilariously peculiar train chase in movie history. I saw “The Wrong Trousers” at a 1994 animation festival and have never laughed harder in my life.—Curt Holman

76. Apollo 13 (Ron Howard, 1995)
Among the most impressive feats of this Ron Howard tour de force is the way that he took an incredibly well-documented true story where everyone knows the ending and made it into such an intensely dramatic nail-biter—thanks, in part, to some reportedly extensive script doctoring by an uncredited John Sayles. Meticulously researched and painfully attentive to accuracy, the film is never more concerned with the nuts and bolts of the science and technology than it is with the humanity of the characters. Tom Hanks, Ed Harris, Kevin Bacon and Bill Paxton are all at the top of their game here.—David J. Greenberg

75. Thelma & Louise (Ridley Scott, 1991)
Don’t call it a chick flick; it’s the ride-or-die movie to end all ride-or-die movies. Ridley Scott directed Susan Sarandon and Geena Davis in the critically acclaimed story about two friends on the road and on the run. In search of adventure they discovered crime, love and that all-too-real freedom that comes at a great cost. With knockout performances from an entire cast (which included Harvey Keitel, Michael Madsen, and baby boy Brad Pitt), Thelma & Louise is that brilliant pop-culture cult-classic that simply cannot be imitated.—Shannon M. Houston

74. As Good As It Gets (James L. Brooks, 1997)
Someday, hopefully far, far away, Jack Nicholson will no longer be making films. It’s a singularly good reason to clone human beings. If that doesn’t work, just repeatedly watch one of his greatest performances, As Good As It Gets. The actor brings all of his talents to the invention of a most fascinating creature: Melvin Udall, a successful romance novelist with a struggling obsessive-compulsive disorder who is also a supremely socially dysfunctional grouch. The man’s life is turned upside down by the violent assault of a gay neighbor (Greg Kinnear) and the medical problems of a waitress’ (Helen Hunt) young son. The interaction between the three adults is movie-making magic with some of the cleverest film dialogue of that decade. Both Nicholson and Hunt received Academy Awards for their roles with Kinnear getting a supporting nomination. But Nicholson performs at such a high level that he doesn’t even need to speak to pull you in. It only takes the raise of an eyebrow or a drop of a jaw. It is good, and it doesn’t get much better.—Tim Basham

73. Austin Powers: The Spy Who Shagged Me (Jay Roach, 1999)
I have a theory about Mike Myers: if you were not a teenage boy growing up in the late 70’s or early 80’s, you’re going to miss so much of his humor. With the “Powers” films and the two “Wayne’s World” films, Myers brilliantly, and hilariously captured something, that hodgepodge of pop culture from the ’60s that permeated the ’70s and morphed into something else in the ’80s. Essentially variations on one joke, a spoof of ’60s spy movies, the ’60s themselves and, by extension, the ’90s, the series began to run out of steam mid-way through this second installment but it certainly has its charms, notably the opening musical sequence.—David J. Greenberg

72. A Taste of Cherry (Abbas Kiarostami, 1997)
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The first Iranian film to win the Palme d’Or at the Cannes Film Festival, Abbas Kiarostami’s controversial Taste of Cherry is a masterpiece of contemplative cinema. In it, middle-aged Mr. Badii (Homayoun Ershadi) drives the dusty hills outside Tehran, seeking a stranger to do him a favor: He intends to kill himself; he’s already dug a grave; he just needs someone to bury him after he dies. It’s a distressing request, though, in a society whose Muslim strictures prohibit suicide. Kiarostami films Mr. Badii’s philosophical conversations with those he approaches—a shy Kurdish soldier who flees from the disturbing request; an Afghani seminary student who tries to talk him out of it; and a Turkish taxidermist who needs the money for his sick child—in long, uninterrupted takes inside his Range Rover. The pace is leisurely and the style minimalist, with lengthy periods of silence, culminating in an enigmatic shot of Mr. Badii, about whom we’ve learned nothing other than he wants to die, lying in his grave as a thunderstorm gathers and meta behind-the-scenes footage of the film being shot.—Annlee Ellingson

71. Sweet and Lowdown (Woody Allen, 1999)
Woody Allen  capped off the ‘90s by creating a character loaded with both tragic flaws and comic gold. Sweet and Lowdown arguably features the best performances both Sean Penn and Samantha Morton have given in their careers. In this pseudo-biopic, Penn plays Emmett Ray, the insecure second-best jazz guitarist of the 1930s, who deep down knows he’ll never be as good as the incomparable Django Reinhardt. Allen and Penn depict a lonely, miserable, thieving, unreliable drunk who happens to be a wonderful musician. In lesser hands, Ray might simply be a comedic buffoon, but Allen knows how to work it from all angles. Morton brings out the humanity with her unforgettable portrayal of a good-hearted mute girl who goes against better judgment to befriend the doomed guitar player.—Michael Dunaway

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