40. Once (2007): A super low-budget, completely charming modern day musical. The songs are lovely, the story simple and sweet. It's definitely movie you remember fondly.
39. 25th Hour (2002): For a Spike Lee movie, it's really only tangentially about race relations. It's mostly about regret, dreams, 9/11, and a deep love for the complexities of life in New York. The story concerns the last hours in New York of a drug dealer (Edward Norton) before he is sent to prison. If I saw this again, I have a feeling it might place even higher.
38. Monsoon Wedding (2002): One of those movies that just makes you feel good. Director Mira Nair paints a vivid picture of a modern Indian family gathering around the arranged marriage of their daughter. Definitely one that is just as enjoyable on repeat viewings.
37. 4 Months, 3 Weeks, and 2 Days (2008): This Romanian film is about a young woman (Anamarica Marinca) who tries to obtain an illegal abortion for her friend in communist-era Romania. Naturalistic, tense, and hard to shake.
36. Mystic River (2003): While I think Clint Eastwood's output has been a bit hit-and-miss this decade (although Million Dollar Baby almost made my list), this is a definite hit. A crime procedural with lots more going on under the service. Sean Penn, Tim Robbins, and Marcia Gay Harden are all superb.
35. Best in Show (2000): I've probably seen this Christopher Guest mockumentary movie more than any other film on the list. The portrait of dog show attendees is eminently quotable. My favorite characters? Eugene Levy and Catherine O'Hara as mismatched terrier owners.
34. American Splendor (2003): Based on autobiographical comic books by Harvey Pekar, this movie combines live action, comic books, and even a little documentary. The movie really captures the lives of those who live on the edge of mainstream society. It's really funny, really moving, and has great performances by Paul Giamatti and Hope Davis.
33. Wonder Boys (2000): If I was making a list of the most overlooked films of the decades, this would definitely be on it. Michael Douglas plays Grady, a college professor with writer's block and a weekend of interactions with others. Not a ton of plot, but the actors (including Frances McDormand, Tobey Maguire, and a pre-Tom Katie Holmes) and the atmosphere are so winning.
32. Milk (2008): Sean Penn again. He turns in a great performance as groundbreaking gay politician Harvey Milk. A biopic that, instead of being about an entire life, is really about a political awakening and a political movement. Timely and moving.
31. The Departed (2006): Martin Scorsese finally won his Oscar for this movie (which won Best Picture as well). While not Scorsese's masterwork, it's certainly the best he's been in years. A gripping and fun (despite the copious deaths and blood) cat-and-mouse game between organized crime and the Boston police. Jack Nicholson overacts a bit, but Damon and Dicaprio are the best they've been and Vera Farmiga proves her potential.
For this group, you have a few great movies from abroad (Once, Monsoon, 4 Months), Academy Award favorite (Milk, Mystic River, The Departed) and somewhat overlooked gems (25th Hour, Wonder Boys).
Thoughts on any of these films, readers?