The 40-Year-Old Virgin

A romantic comedy directed by Judd Apatow in his feature directorial debut. Steve Carell (who co-wrote the screenplay) stars as Andy Stitzer, a 40-year-old electronics store employee whose co-workers discover he is a virgin and set out to help him lose his virginity. Catherine Keener co-stars as Trish, a woman Andy falls for. The film grossed $177 million worldwide and was named one of AFI's Top 10 Films of 2005