Jon Cryer. Actor: Two and a Half Men. Jonathan Niven Cryer is an American actor, comedian and filmmaker. Born into a show business family, he made his motion picture debut as a teenager photographer in the 1984 romantic comedy No Small Affair; his breakout role came in 1986, in the John Hughes-written film Pretty in Pink. In 1998, he wrote and produced the independent film Went to Coney Island on...