In the battle to decide the greatest movie year in American history, 1999 can duke it out with the best of ’em. The year has some very worthy opponents—most notably, Hollywood’s Golden Year, 1939, which saw an increase in theater attendance and a dazzling array of classics like The Wizard of Oz, Mr. Smith Goes to Washington, Gone With the Wind, and more. But even a quick scan of movies that premiered in 1999, 60 years later, reveals a near-dizzying, exhaustive list of box office hits and flops-turned-cult classics that remain just as relevant in pop culture today as they were 22 years ago. Esquire once declared 1999 “The Last Great Year in Movies,” and though the distinction can (and will) be endlessly debated, 1999 was indeed a special year in American cinema.
The eve of the new millennium prophesied an entirely new era in Hollywood, one characterized by advancements in computer-generated imagery, avant-garde original storytelling, and the rising influence of digital video. The emergence of new auteurs like M. Night Shyamalan and Spike Jonze stole the film scene. Whereas today, Hollywood is so often focused on reboots, remakes, spinoffs, and franchises, many of the movies of 1999 were well-executed projects born from exciting original ideas. A concept!
From innovative science fiction masterpieces like Lana and Lilly Wachowski’s The Matrix, to internet-savvy “found footage” horror flick The Blair Witch Project, read on for a collection of some of the best movies of 1999.
The Sixth Sense
M. Night Shyamalan’s psychological ghost thriller gave the world the memorable line: “I see dead people.” It also gave people one of the most famous twists in film history. The film follows a child psychologist (Bruce Willis) as he tries to help a young boy (Haley Joel Osment) who can talk to ghosts.
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The Matrix
The influence of this mind-blowing, ahead-of-its time masterpiece still radiates through the sci-fi genre today. To attempt to summarize it is a futile exercise, but here goes: Keanu Reeves plays a computer programmer/hacker who discovers he is living in a simulated reality. As Morpheus says: “Unfortunately, no one can be told what the Matrix is. You have to see it for yourself.”
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Fight Club
Everyone knows the first rule of fight club. But evidently no one followed it, because David Fincher’s Fight Club is one of the most talked-about films of the Y2K era. The cult classic, based on the Chuck Palahniuk novel, follows an unnamed insomniac narrator (Edward Norton) who forms an underground fight club with a handsome, reckless soapmaker (Brad Pitt).
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The Talented Mr. Ripley
An adaptation of the Patricia Highsmith novel, The Talented Mr. Ripley asks the thrilling question: what if you could live someone else’s life? The combination of the stunning Amalfi coast setting and a stacked young cast (Matt Damon, Jude Law, Gwyneth Paltrow, Cate Blanchett, Philip Seymour Hoffman) creates a film that shimmers with a darkness at its core.
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Eyes Wide Shut
Stanley Kubrick’s last film is an erotic thriller that unfolds like a nightmare, drifting between dream and reality. The story follows Bill and Alice Hartford (Tom Cruise and Nicole Kidman, who were married in real life at the time) as they explore the sexual underworld of 1990s New York City.
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Being John Malkovich
Spike Jonze‘s and Charlie Kaufman’s feature debut is a bizarre and clever spoof on celebrity culture, in which an unemployed puppeteer (John Cusack) takes a temp job and discovers a hidden portal into the mind of movie star John Malkovich.
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Boys Don’t Cry
Kimberly Peirce’s independent film is based on the true story of Brandon Teena, a young trans man who fell in love with a woman in a small Nebraska town, and was heinously killed in a hate crime in 1993. The film has a complex and nuanced legacy today, but remains vital for its role in paving the way for trans representation in film.
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Election
In this political satire, Reese Witherspoon nails the role of Tracy Flick, an overachiever who campaigns to be high school president, and will stop at nothing to win—no matter her opponent (Matthew Broderick, as her meddlesome teacher).
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The Blair Witch Project
As the story goes, three film students went into the woods to make a documentary about a terrifying local legend, only to vanish. The shaky “found footage” and manufactured internet mythology made for a massive blockbuster that popularized the documentary-style horror genre.
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The Green Mile
Tom Hanks shines in this moving supernatural drama based on Stephen King’s novel of the same name. Hanks plays a death row correctional officer who’s confronted by a man with miraculous powers, whom he suspects has been wrongfully convicted of murder.
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American Pie
It’s a time-honored teenage comedy setup: a group of high school guys try to have sex before prom night. But American Pie endures because it’s one of the grossest, funniest, most ridiculous spins on the setup. It will have you shaking your head even as you laugh at the cast (Jason Biggs, Tara Reid, Alyson Hannigan, Seann William Scott, Natasha Lyonne) and their many shenanigans.
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Austin Powers: The Spy Who Shagged Me
In the peak of the blockbuster franchise, Mike Myers’s iconic spy travels back to the groovier times of 1969 to save the world from Dr. Evil and recover his “mojo.”
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10 Things I Hate About You
As far as modern spins on Shakespeare go, high school romantic comedy 10 Things I Hate About You is very, very good. See: Heath Ledger’s performance of “Can’t Take My Eyes Off You” or Julia Stiles drunkenly dancing to “Hypnotize” in one of the greatest party scenes around.
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Go
Go is a Tarantino-esque youth culture dramedy that unfolds over the course of a single day, following three interweaving perspectives on a drug deal and a wild night.
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The Hurricane
In this biographical sports film, Denzel Washington gives a remarkable performance as Rubin “The Hurricane” Carter, a boxer whose championship dreams were shattered when he was wrongfully convicted of murder in 1967.
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American Beauty
Of all the films on this list, American Beauty may have aged the most poorly. The darkly comedic portrayal of suburban strife has a disturbing Lolita factor, and Kevin Spacey as its star. (Big yikes). But the film won Best Picture and made an undeniable, if divisive, mark on pop culture with its rich visual palette and attempt to beautify a plastic bag.
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Office Space
Mike Judge satirizes workplace culture in this cult classic, in which a software company employee decides he wants to get fired and winds up teaming up with his two laid-off friends to embezzle money from the company.
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The Virgin Suicides
Sofia Coppola’s feature debut adapted the Jeffrey Eugenides novel and sparkled with artful cinematography, a fantastic soundtrack, and dreamlike, somber performances from its young cast. The story follows a group of neighborhood boys as they fantasize about and analyze the Lisbon sisters, who are isolated in their house under strict watch by their parents after the youngest sister attempts suicide.
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Magnolia
Paul Thomas Anderson‘s follow-up to Boogie Nights is a very long (3+ hours) psychological drama with a phenomenal ensemble cast. If you give it your time, you’ll be met with a moving portrait of interconnecting stories about loneliness and the human condition.
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The Insider
Based on a Vanity Fair article, The Insider is director Michael Mann’s fictionalized account of a tobacco industry whistleblower (Russell Crowe) and the 60 Minutes producer (Al Pacino) who fought to bring his truth to light.
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Anna Grace Lee
Anna Grace Lee is an editorial fellow at Esquire, where she covers pop culture, music, and entertainment.
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