20. My Big Fat Greek Wedding (dir. Joel Zwick)
In the running for my most rewatched film ever, Nia Vardalos’s sweet-natured rom-com has endured. While it lacks the sophistication of some of the genre’s masterpieces, its comic timing and sense of identity are top-notch. It also has time for little moments of pure humanity. It’s a shame none of her other ventures – including sequels to this film – found that register.
19. 13 Conversations About One Thing (dir. Jill Sprecher)
An early example of the decade’s trendy “hyperlink” movie (to borrow a phrase from the late, great Roger Ebert), it blows all the others out of the water, including a certain notorious Best Picture winner. Each of its four main characters rides high and gets laid low, and the film chronicles their journeys without judgment. But it wouldn’t work without its excellent cast, including a pre-renaissance Matthew McConaughey and the incomparable Alan Arkin, whose role as a weary insurance investigator fits him like a glove.
18. About Schmidt (dir. Alexander Payne)
Payne has often been accused of mocking his midwestern characters, but the joke is actually on the selfish, uptight Warren (Jack Nicholson, in his funniest role). After the death of his wife, he goes on a road trip to stop his daughter’s wedding. While his future in-laws are loud, crude and susceptible to pyramid schemes, they’re far more welcoming and vivacious than he ever was.
17. Road to Perdition (dir. Sam Mendes)
In what may or may not be a surprise to you, this was the first R-rated movie I saw in theaters. While it occasionally struggles with tone, this gorgeous adaptation of Max Allan Collins’s graphic novel features a powerful but restrained turn from Tom Hanks, a marvelously nasty villain role for Jude Law, and an early look at Daniel Craig’s greatness, playing the Fredo of this Irish crime family.
16. Chicago (dir. Rob Marshall)
Over the course of 20 years, I’ve gone back and forth on this movie. I was initially dazzled, but found it more style than substance as I grew older. Revisiting it recently, what struck me was the bone-deep cynicism, a hallmark of Kander & Ebb’s music. And while the film racked up four acting Oscar nods including a win, Richard Gere (who has somehow never been nominated) impressed the most as the gladly amoral Billy Flynn.
15. 24 Hour Party People (dir. Michael Winterbottom)
More biopics should follow the lead of this comedy: Some of it’s true, a lot of it’s exaggerated, and a little bit is just straight-up fiction. Steve Coogan is absolutely dynamite as the founder of Factory Records. He knows good music and how to throw a party, but knows zilch about business. It goes about as well as expected. It may not have been a sound enterprise, but it resulted in some killer tunes, as evidenced by the year’s best soundtrack.
14. The Quiet American (dir. Phillip Noyce)
Graham Greene’s novel about American and European interlopers in Vietnam got a morally repugnant adaptation in 1958, with an uncredited rewrite by the CIA, making the U.S.A. the good guys. This version stays true to the novel, but it’s not as if it turns Michael Caine’s Fowler into a hero. He’s already been morally compromised, but even he can see through the flat-out evil plan pushed into action by Alden Pyle (Brendan Fraser, in one of his best roles). Shelved for a year after 9/11, it is downright anti-American. It’s also clear that it must be.
13. Punch-Drunk Love (dir. Paul Thomas Anderson)
PTA harnessed Adam Sandler’s raging man-child energy into this lovely, stunning and concise romantic comedy. Jon Brion’s score, Philip Seymour Hoffman’s unhinged turn and a nagging sense it could all go awry at any moment make for a sneakily potent film.
12. Signs (dir. M. Night Shyamalan)
Internal logic be damned. This is my favorite film from the man who would be “The Next Spielberg.” While some of his other films might be tighter or more daring, this is a patient, nakedly emotional film about four broken people facing an inexplicable situation. While its religious themes and implications are clear, it’s a story about faith that can be applied pretty liberally. Even if you don’t believe in God or extra-terrestrials, you can believe in each other, even in the toughest of circumstances.
11. Talk to Her (dir. Pedro Almodóvar)
Spain’s finest director finally won a long-overdue Oscar for this script about two men and the comatose women they love. But his commitment not to judge his characters becomes a challenge when one of them does something unforgivable. But that’s just one of the incredible things about this film! Even though much of it takes place in hospital rooms (and later, a prison), there’s a ton of eye-popping color. And an X-rated black-and-white film within a film is magical, provided you’re not a prude. It may not be Pedro’s greatest film, but it’s one of his most emotionally complex and thoughtful.
