Remember, the point of these things is to argue about them. Here goes:
Runners up: Gosford Park, Borat, Capturing the Friedmans, Punch-Drunk Love, Wall-E, Erin Brockovich, Syriana, Y Tu Mama Tambien, Far from Heaven, No Country for Old Men, The Royal Tenenbaums
20. Anchorman: The Legend of Ron Burgundy
19. Eternal Sunshine of the Spotless Mind
18. Requiem for a Dream
16. Pirates of the Caribbean: The Curse of the Black Pearl
15. Crouching Tiger, Hidden Dragon
13. Lost in Translation
11. Being John Malkovich
10. Grizzly Man
7. Iron Man
6. The 40-Year-Old Virgin
5. A Mighty Wind
4. There Will Be Blood
3. O Brother Where Art Thou
This and The Big Lebowski are still for my money better than anything the Coen brothers have done since. Perfect synthesis of kitschy stoner comedy and archetypal detective story.
2. The Lord of the Rings trilogy.
I am counting them together as one film. One of the great achievements in all of movie history. If I have to choose a favorite, I choose "The Two Towers."
1. The New World
My second-favorite film by my favorite director, Terence Malick. (Favorite would be Days of Heaven.) I love the way this movie really lets you see through the eyes of the first American settlers as they encounter the hopelessly alien "Naturals," their word for American Indians. Later, the film captures the same sense of strangeness for Pocahontas on her first encounter with Europe. It's also a disquisition on the (sometimes false) idea of paradise and the (sometimes prosaic) nature of love. And its nature photography is absolutely gorgeous.
I am not quite sure why, but I think my taste in television shows is much closer to the critical conventional wisdom than is my taste in music or movies. Arguably that makes this my most boring list. Still, these are all great shows:
15. The Colbert Report
13. The West Wing
12. Mad Men
11. The Sopranos
9. 30 Rock
8. Veronica Mars
7. Battlestar Galactica
6. The Daily Show
4. The Office (American)
3. Arrested Development
2. Buffy the Vampire Slayer
1. The Wire