While I plan on continuing this project for years, this pandemic didn’t exactly make this project easier. “Free time” really felt like a myth, so I ran out of time to revisit more of these titles, which might have resulted in a slightly different list, particularly in the 11-20 range. But this mix of old and new favorites once again shows us how good we once had it.
20. Unbreakable (dir. M. Night Shyamalan)
After the success of The Sixth Sense, anticipation was sky-high for his next film. Despite a fantastic trailer, the film couldn’t help but feel a little underwhelming. But given two decades, its deconstruction of superhero myths looks much better, especially as film and TV have been swallowed whole by comic book adaptations. Like Shyamalan’s best films, the genre trappings are a Trojan horse for quiet family stories and broken people forging connections .
19. Quills (dir. Philip Kaufman)
There’s really no biopic quite like Quills, which uses the Marquis de Sade’s last year at a French insane asylum as a springboard to explore sexuality, freedom, religion and power. Geoffrey Rush – in an Oscar-nominated turn – dazzles as de Sade, who lives life with no filter, a provocateur to the very end. While it bears little resemblance to real life, it’s an unforgettable film about the very real power of words.
18. Love & Basketball (dir. Gina Prince-Blythewood)
One of the most confident debuts of all time, Gina Prince-Blythewood shoots and scores. Sanaa Lathan and Omar Epps have chemistry that radiates off the screen, making the film romantic, sexy and compelling. (Harder than it looks.) While the film can’t help but come up against some clichés, it more than makes up for it by accurately depicting the gulf of opportunities for male and female athletes after college.
17. Hamlet (dir. Michael Almereyda)
Michael Almereyda updates Shakespeare’s revenge tale for the world of hostile corporate takeovers, capturing Ethan Hawke at his hipster peak. He delivers the famous “To be or not to be” monologue in a Blockbuster, a wild swing they pull off. Its use of modern (for the end of the 20th Century) technology actually keeps it from being dated. Instead, it gives it a surreal, detached quality that absolutely works in the film’s favor.
16. Wonder Boys (dir. Curtis Hanson)
Out of his long and storied career, this is my favorite Michael Douglas performance. Grady Tripp’s life and novel are a bigger mess than he’d care to admit, yet he’s constantly putting himself out there for other people. He walks through life with a smile and a joint. The film’s supporting cast is phenomenal, including the always reliable Frances McDormand and Rip Torn, plus a trio of actors pre-superhero fame (Katie Holmes, Tobey Maguire and Robert Downey Jr.) The crackling, Oscar-nominated script by Steve Kloves won him the gig adapting the Harry Potter series. But oh, what could have been if he’d taken a crack at other Michael Chabon novels.
15. American Psycho (dir. Mary Harron)
More than a decade ago, I cited Christian Bale as one of the best performances of the century so far. That’s still true, even as he’s given more intense and more nuanced turns in the years since. But American Psycho stands out for more than that. Mary Harron’s satirical, pitch black comedy improves on its source material in every way, with an exploration of the literally cutthroat world of Wall Street bros that hasn’t aged a day.
14. Requiem for a Dream (dir. Darren Aronofsky)
Here’s a movie I absolutely have no plans to revisit. Schools should just show this to kids instead of D.A.R.E. programs. There have been plenty of movies made about drug addiction, but none this visceral and horrifying. Ellen Burstyn should have won the Oscar for her portrayal of Sara Goldfarb, already teetering on the edge of sanity when she becomes addicted to amphetamines. Her son (Jared Leto) is even further down the hole of heroin addiction, dragging his friend (Marlon Wayans) and girlfriend (Jennifer Connelly) down into hell with him. It’s stylish but unrelentingly depressing. An experience you’ll never forget.
13. Remember the Titans (dir. Boaz Yakin)
For Millennials, it’s a safe bet that this is in their most rewatched films of all time. Or at least I’m assuming that to be the case, based on how many times teachers who just wanted to pop in a video and do some grading threw this on in middle school and high school. Denzel Washington and Will Patton – a pairing I wish had happened more often – are terrific, the football scenes are rousing, and the soundtrack is nothing but classics. But it’s also a stronger film about race relations than some recent Oscar nominees. (Looking at you, Green Book and Hidden Figures.)
12. Snatch (dir. Guy Ritchie)
This is Guy Ritchie at the peak of his powers: A wild, twisty, devilishly entertaining crawl through the London underworld in search of a diamond. The jewel, of course, doesn’t matter. It’s just a way to bring a bunch of dangerous but thrilling characters together. Chief among them is Brad Pitt’s Mickey, who steals the film in an unhinged turn as a nomadic fighter.
11. Beau Travail (dir. Claire Denis)
I didn’t totally connect with this extremely loose adaptation of Billy Budd when I first saw it a few years ago. But Denis’ images have burned into my brain. Denis Levant is the chain-smoking trainer of a battalion of the French Foreign Legion. In the sweltering Djibouti sun, he becomes obsessed with a new cadet (Grégoire Colin), and vows revenge when the feelings are unreciprocated. Even with minimal dialogue, its themes of desire, anger and desperation are the same in any language.
10. Bamboozled (dir. Spike Lee)
Bamboozled is an ugly film, both in topic and look. Shot on digital video in the format’s infancy, it’s tough to look at, but that’s the point. This is a media satire even more vicious than Network. Tired of his racist boss (Michael Rapaport), a burnt-out TV executive (Damon Wayans) comes up with an idea sure to get him fired: a modern day minstrel show. But just as in The Producers, he ends up with a massive hit on his hands. This might be the most in-your-face film Spike Lee has ever made, but it’s also one of his best.
9. O Brother, Where Art Thou? (dirs. Joel & Ethan Coen)
The Coens’ sepia-toned adaptation of The Odyssey is one of the most beloved by folks who aren’t Coen obsessives like me. It’s easy to see why: Everyone knows the story, the main trio are immediately engaging, it’s funny as hell, and that soundtrack of period-appropriate music was a full-blown phenomenon. But that undersells how deeply weird this movie is, and how committed it is to ahistorical fantasy. (The film ends by the townspeople rejecting a KKK member and politician.)
8. You Can Count on Me (dir. Kenneth Lonergan)
One of Lonergan’s gifts has always been in crafting flawed characters we can’t help but root for. He also excels at finding moments of levity in the aftermath of tragedy. His film debut is filled with both. When family screw-up Terry (Mark Ruffalo) comes to visit his uptight sister Sammy (Oscar nominee Laura Linney), their dynamic completely flips. Terry starts to get it together while Sammy starts acting out and falling apart. But they’re still there for each other and love each other, even if they have a funny way of showing it.
7. Traffic (dir. Steven Soderbergh)
Though its racial politics haven’t aged particularly well, this sprawling saga of the War on Drugs is appropriately bleak. There are no winners in this fight, only pawns and losers.
6. The Virgin Suicides (dir. Sofia Coppola)
A hipster urtext, Sofia Coppola’s debut is a marvelous thing, and the end of a tremendous run for Kirsten Dunst, who also starred in Dick and my No. 6 film of 1999. While the performances and writing are top-notch, the film’s strongest aspect is its intoxicating atmosphere.
5. State and Main (dir. David Mamet)
David Mamet has written better films, but he’s never written anything funnier. Giving his rapid-fire dialogue to an incredible ensemble cast, hardly a moment goes by without a hearty laugh. The troubled film production goes from bad to worse when the amoral cast and crew relocate to Vermont in search of a nonexistent mill. Only the pretentious screenwriter (Philip Seymour Hoffman) has anything resembling a conscience, and his desire to do the right thing exacerbates the on- and off-set crises.
4. Best in Show (dir. Christopher Guest)
The best of Guest’s mockumentaries, the weirdoes at this dog show are all indelible characters. While each of the competitors is extremely neurotic but quite endearing (except the insufferable yuppies played by Parker Posey and Michael Hitchcock), it’s Fred Willard who steals the show as the color commentator, constantly interrupting his expert co-host (Jim Piddock) with inappropriate questions.
3. High Fidelity (dir. Stephen Frears)
Top 5 things I love about High Fidelity:
5. Jack Black’s soulful rendition of “Let’s Get It On”
4. Lisa Bonet
3. The Bruce Springsteen cameo
2. Making Rob kind of an asshole, which keeps you from viewing him with rose-colored glasses
1. How incredibly relatable it is for a music nerd like me
2. Crouching Tiger, Hidden Dragon (dir. Ang Lee)
Martial arts films were certainly nothing new, but there had never been one on this scale before, or at this level of international success. (It’s still the only foreign language to make more than $100 million in the U.S.)
The action scenes are still jaw-dropping, putting most modern films to shame. The performances are terrific across the board, particularly Zhang Ziyi as the defiant Jen Yu. And everywhere you look, there’s something beautiful to see. This is filmmaking on the grandest possible scale.
1. Almost Famous (dir. Cameron Crowe)
An all-time favorite that’s only grown in my estimation over the last 20 years. Hired by Rolling Stone to cover Stillwater’s tour just as they’re about to hit the big time, William (Patrick Fugit) learns a lot of lessons the hard way. Yet Crowe, whose script is based on many of his real-life experiences, still makes life on the road seem magical. This is his masterpiece, and he got career-best performances from Fugit, the Oscar-nominated Kate Hudson, and Billy Crudup. How he didn’t become the biggest movie star in the world after this remains one of Hollywood’s greatest mysteries. Now one more time, here’s “Tiny Dancer.”
Billy Elliot (dir. Stephen Daldry)
Bring It On (dir. Peyton Reed)
But I’m a Cheerleader (dir. Jamie Babbit)
Cast Away (dir. Robert Zemeckis)
The Cell (dir. Tarsem)
Chicken Run (dirs. Peter Lord and Nick Park)
The Emperor’s New Groove (dir. Mark Dindal)
Fantasia 2000 (various directors)
George Washington (dir. David Gordon Green)
Ghost Dog: The Way of the Samurai (dir. Jim Jarmusch)
The House of Mirth (dir. Terrence Davies)
Jesus’ Son (dir. Alison Maclean)
Miss Congeniality (dir. Donald Petrie)
The Patriot (dir. Roland Emmerich)
Return to Me (dir. Bonnie Hunt)
Shadow of the Vampire (dir. E. Elias Merhige)
Shanghai Noon (dir. Tom Dey)
The Tao of Steve (dir. Jenniphr Goodman)
Tigerland (dir. Joel Schumacher)
Yi Yi (dir. Edward Yang)