Jon Cryer is the comic actor who plays opposite Charlie Sheen in the television series Two and a Half Men. Cryer made his film debut as a love-struck teen in the 1984 comedy No Small Affair (opposite Demi Moore), and he remains famous for one of his earliest roles, as "Duckie," Molly Ringwald's geeky pal in the 1986 movie Pretty in Pink. Cryer went on to appear in the movies Superman IV: The Quest for Peace (1987, starring Christopher Reeve), Dudes (1987) and Hot Shots (1991, with Sheen), but since the 1990s most of his work has been in television. After several failed series -- The Famous Teddy Z (1989), Partners (1995) and The Trouble with Normal (2000) -- Cryer hit it big in 2003 with the success of Two and a Half Men. Nominated four times for an Emmy, he won in 2009 as best supporting actor in a comedy.