35) The 40 Year Old Virgin (2005, dir. Judd Apatow)
Starring Steve Carrell, Paul Rudd, Kathrine Keener, Romany Malco, Seth Rogen
One of my favorite comedic auteurs of the 2000s was Judd Apatow. His season long creation Freaks and Geeks still stands as one of the most enjoyable and thoughtful portraits of adolescence and the one I feel the most connection to. His feature film debut was just as thoughtful, though also a full of ribald humor. The plot concerns, Andy (Carrell), an electronics store employee whose secret that he is still a virgin in his 40s comes out during a coworker poker game. His coworkers (Rudd, Rogen, Malco) take it upon themselves to di-virginize Andy in attempts that don't end at all how they intend. Andy eventually meets Trish, a single mom who had immediate chemistry with him. As the relationship progresses, Andy feels the pressure of sex increasing. While there are lots of f-bombs and sex humor, the film is not making Andy the butt of the joke but rather his more sexually experienced coworkers. For all their conquests they are buffoons and in the end its Andy who discovers the most honest and true version of love.
34) Wet Hot American Summer (2001, dir. David Wain)
Starring Janeane Garafalo,David Hyde Pierce,Michael Showalter,Paul Rudd,Michael Ian Black,Christopher Meloni
This was my first exposure to the brilliant comedy troupe known as The State. After having a successful skit series on MTV in the 1990s for three years, the group worked individually until the majority of them were reunited for this feature. The plot is loose satire of 1980s summer camp movies, but instead of being simple parody the writers and actors chose to make it full of high absurdity. The humor goes to dark, extremes that increases the shock laughs. The story follows Coop (Showalter) who has a stereotypical "geek loves hot girl" crush and is challenged by the girl's boyfriend (Rudd). Simultaneously, camp director Beth (Garafalo) is smitten with astrophysicist, Henry. Their relationship plays out with hilarious absurdity and culminates with a 20-sided die diverting an astronomical disaster.
33) Donnie Darko (2001, dir. Richard Kelly)
Starring Jake Gyllenhaal, Jena Malone, Maggie Gyllenhaal, Patrick Swayze
As time has gone on, the magic of this film has decreased slightly for me but it still holds a certain sentimentality that sticks. Richard Kelly made a very strong debut with this film that tells the tale of the mentally disturbed Donnie Darko. Set in Virgina during 1988, Donnie suffers from sleepwalking and ends up wandering from the house one night and encountering a man in a skull-faced rabbit suit. The man tells him the world has 28 days remaining. While Donnie is out of the house his room is flattened by a jet engine that has mysteriously fallen out of nowhere. Life continues and Donnie's bizarre trances increase and he discovers an enigmatic tome that informs him about time travel. While the ending of the film provides more questions than answers, it is a very tightly written script. Kelly has a very stark aesthetic influenced by many 1980s directors, particularly Robert Zemeckis. Sadly, Kelly has yet to live up to this debut.
32) Brokeback Mountain (2005, dir. Ang Lee)
Starring Heath Ledger, Jake Gyllenhaal, Michelle Williams, Anne Hathaway
Director Ang Lee continually surprises me with how he can genre jump like no other. From Sense & Sensibility to The Ice Storm to Crouching Tiger Hidden Dragon to Hulk, I don't believe there is another director so adept at taking on such diverse styles. With Brokeback Mountain, Lee tells a love story that is taboo to many people but does so in a quiet, respectful way. Ennis (Ledger) is a ranch hand looking for work in Wyoming in 1963. He ends up herding sheep for the summer alongside Jack (Gyllenhaal). The two men maintain a quiet relationship until one night when Jack makes a sexual pass at Ennis. Ennis responds and the two men make love, spending the summer growing closer and closer. At the end of their time working, Ennis distances himself believing that whatever they had cannot continue further. Despite moving on and marrying, the two men find opportunities to reunite and try to recapture that time on their own. Brokeback Mountain is one of the most beautiful and tragic love stories of the decade and earned Lee a very well deserved Oscar win.
31) American Splendor (2003,dir. Robert Pulcini & Shari Berman)
Starring Paul Giamatti, Hope Davis, Judah Friedlander, James Urbaniak, Harvey Pekar
American Splendor is one of the most unusual comic book adaptations of the 2000s. While this is an origin story, there are no capes or tights. Instead its vintage records and perpetual scowls. Cleveland native, Harvey Pekar began chronicling his life in underground comic books in the 1970s after befriending cult comix artist Robert Crumb. The film works as a docudrama, that features the real Pekar commenting on his life mixed with Giamatti acting out the anecdotes. Even the illustrations from the comic books are animated and spliced amongst the live action sequences. The entire form and style of this film is unlike any other I have seen and have not seen it attempted since. Giamatti does an excellent job mimicking Pekar, but if you have seen the film you can agree nothing surpasses the natural curmudgeon of the original.
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