Many people, myself included, consider 1999 to be the best movie year ever. I’m even reading a book called just that. It seemed like the last time multiple studios were willing to gamble on unique visions and give sizable budgets to things that weren’t based on previously existing properties. So I figured 2019 was the perfect time to kick off a project picking the 20 best movies from 20 years ago. Unfortunately, with so much time devoted to Best of the Decade posts, that can got kicked down the road. Better late than never, I suppose.
20. 10 Things I Hate About You (dir. Gil Junger)
Were it not for Amy Heckerling’s Clueless, this would be the best high school movie of the ’90s. I’m sure it’s not a coincidence both are based on classic British literature. This ultra-hip (loose) adaptation of Shakespeare’s The Taming of the Shrew has the unstoppable charm of its main cast, including the late Heath Ledger, but it’s also got a murderer’s row of a bench, with the likes of Larry Miller, Allison Janney and Daryl “Chill” Mitchell providing even more laughs as the adults who are just as immature as the kids. It’s also got an all-time villain in Andrew Keegan’s Joey, a skeevy, vain senior, who responds to a well-deserved punch in the face with, “Shit, Bianca! I’m shooting a nose spray commercial tomorrow!”
19. The Blair Witch Project (dirs. Daniel Myrick, Eduardo Sánchez)
When it came to pre-social media discussions, only Star Wars: Episode I – The Phantom Menace was talked about more. While this low-budget found footage horror flick ended up as the most profitable movie of all time, it didn’t do much for me when I saw it on VHS as a kid. But once you know its tricks, you’re far more open to appreciating its craft (exceptional for first-time feature directors) and how a bunch of drunk assholes getting lost in the woods is actually a more terrifying and realistic scenario than whatever evil it is they find out there. But then and now, its shocking ending strikes a nerve.
18. Fight Club (dir. David Fincher)
It’s best to view David Fincher’s adaptation of Fight Club as a movie about cults. The misguided men who follow Tyler Durden (Brad Pitt, magnetic and slyly hilarious) aren’t any smarter after learning about the evils of capitalism and consumerism. They end up picking fascism, blindly following Tyler just like they were the banal lifestyles they were living before. They’d rather show off with brash, pointless stunts and beat the shit out of each other than actually cause a revolution. But I guess that’s why it’s just called Project Mayhem. It’s not wrong that so many college bros are obsessed with this movie. It’s got exceptional craft and it’s a vast improvement over its source material. But like the members, they’re too blind to see beyond how cool it is.
17. Notting Hill (dir. Roger Michell)
The platonic ideal of the ’90s romantic comedy, Notting Hill has it all: Pitch-perfect performances and chemistry between its two leads (Julia Roberts and Hugh Grant), a goofy roommate/best friend (Rhys Ifans), and Richard Curtis’s richly drawn supporting characters (including future lord Hugh Bonneville). While its climactic line has often been mocked, I’m just a critic, standing before my readers, reminding them it’s perfect.
16. Being John Malkovich (dir. Spike Jonze)
A comedy so overflowing with ideas that some of them spill over and don’t get resolved, the brilliant marriage of Charlie Kaufman’s script and Spike Jonze’s direction explodes into the most creative film of 1999. Unlike the future world of Her, pretty much everyone in Being John Malkovich is a selfish prick, pushing everyone in their small space out of the way to get a little bit of a new experience. The cast is turning in some of their best work, but the movie wouldn’t get to that next level without John Malkovich’s wild turn as himself.
15. Election (dir. Alexander Payne)
As humorists try to wring something, anything out of our current climate, Jim Taylor and Alexander Payne were nailing the ultimate political satire in their adaptation of Tom Perrotta’s novel. Reese Witherspoon shines as Tracy Flick, a straight-A student who wants to be class president. Not because she has any radical ideas or brilliant policies, but because it will be another feather in her cap on her way to a prestigious school. Standing in her way are a petty teacher (Matthew Broderick, marvelously pathetic), the dim-bulb athlete he recruits to run against her (Chris Klein), and the jealous sister (Jessica Campbell) who enters as a third-party candidate, rightfully pointing out no one’s lives will be measurably improved by either of them. The jokes cut more sharply here because all of its characters have devious ulterior motives (except naive Paul), making it all the more representative of our elected leaders.
14. The Limey (dir. Steven Soderbergh)
Soderbergh’s lean revenge thriller becomes something more powerful thanks to its unusual editing techniques, its curdled vision of Laurel Canyon artists, and its crucial decision to include flashbacks in the form of scenes from Ken Loach’s Poor Cow. Terence Stamp is phenomenal as the lifelong criminal who travels to L.A. to hunt down his daughter’s killer, using his confidence and daring when he’s outnumbered and outmatched. Think of it as Taken for people who subscribe to the Criterion Channel.
13. American Movie (dir. Chris Smith)
Few scripted films are funnier than Chris Smith’s essential documentary. Mark Borchardt is a Wisconsin burnout working with limited funding and even more limited talent to finish Coven, a black-and-white horror short, hoping to turn what he sees as its inevitable success into financing for Northwestern, a feature-length Gen X epic. Alas, between back taxes, child support, poor carpentry skills and a lack of time, the rush to finish Coven never feels like a sure thing. But the marvelous cast of characters (including the sublime Mike Schenk, with a flowing mane of hair and a never-ending supply of drug stories) keep you laughing and keep you rooting for Mark the whole way.
12. Toy Story 2 (dir. John Lasseter)
Initially slated to go straight-to-video, Pixar eventually put all their resources into their first sequel ever (and first of three sequels to Toy Story). While Woody’s quest for belonging would continue to be explored in 3 and 4, it’s most poignantly told here, as he learns he’s part of a collector’s series of Western-themed toys tied into the Howdy Doody-esque Woody’s Round-up. Its smartest choice is introducing Jessie, terrifically voiced by Joan Cusack, responsible for the first classic Pixar tear-jerker.
11. Go (dir. Doug Liman)
After this, Liman would exclusively direct big-budget fare, but he went out on a high note with this low-budget (and occasionally permit-free) dark comedy about drug pushers and users, and their intersecting lives on Christmas Eve. Sarah Polley plays a broke cashier out of her depth in the rave scene, her co-worker (Desmond Askew) has ditched work for a crazy Vegas weekend, and two actors (Jay Mohr and Scott Wolf) are forced to work a drug bust for a handsy detective (William Fichtner). Connecting them all is Todd (Timothy Olyphant), the charming dealer who can turn menacing on a dime. Seen initially as a Tarantino knock-off (the DVD cover even boasts a pull-quote from Entertainment Weekly calling it “Son of Pulp Fiction“), it’s endured because of its excellent cast, terrific soundtrack and go-for-broke energy.
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