The 40-Year-Old Virgin(2005)
Better late than never.
Acclaimed writer/director/producer Judd Apatow made his big-screen debut with this R-rated Steve Carell-starring comedy. During an innocent poker game with his pals (Seth Rogen, Paul Rudd, Romany Malco), the unintentionally abstinent Andy (Carell) accidentally reveals that he's a virgin. His buddies, all stunned, make it their mission to get him laid. But when Andy starts to bond with a nice, single mother (Catherine Keener), the pressure only, er, mounts. Co-stars Elizabeth Banks, Kat Dennings and Leslie Mann.