4. The 40 Year-Old Virgin (2005)
Director: Judd Apatow
Stars: Steve Carell, Catherine Keener, Paul Rudd, Romany Malco, Seth Rogen, Elizabeth Banks, Jane Lynch, Kat Dennings
The movie that turned Judd Apatow from failed TV producer into film comedy god is two solid hours of hilarious jokes on a can't-beat premise, and that's not counting the awesome outtakes. You know we know you're gay if you didn't cut for this flick.