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.