Vomiting on Steve Carrell in The 40-Year-Old Virgin (2005)
Leslie reunited with her producer/director hubby, Judd Apatow, for this raunchy 2005 flick. Leslie played a minor role as one of Andy Stitzer's dates, Nicky, but she felt her presence known in an infamous drunken car ride. Unbeknownst to Andy, Nicky was quite the wild child, (she even had her own blood alcohol monitoring device!) who had one too many daiquiris and proceeded to puke all over him. That definitely put a wrench into de-virginizing Andy!