About
Jon Cryer is an American actor who began his career in the 1980s with roles in films such as *No Small Affair* and *Pretty in Pink*. He is most recognized for his role as Alan Harper on the CBS sitcom *Two and a Half Men*, for which he won two Primetime Emmy Awards. Cryer has also appeared in films such as *Hot Shots!* and *Superman IV: The Quest for Peace*. His career includes both comedic and dramatic roles in film and television.
Career Timeline
Starts Career in Film
Early roles in 'No Small Affair' and 'Pretty in Pink'.
Pretty in Pink Success
Established his career with this popular film.
Two and a Half Men Premiere
Starred as Alan Harper on 'Two and a Half Men'.
Two and a Half Men peak
'Two and a Half Men' became a huge success, boosting his earnings.
Won Emmy for Two and Half
Won his second Emmy for his performance.
Two and a Half Men Ends
Continued roles in TV after the show ended.
Established TV Actor
Jon Cryer remains a well-known and successful actor.
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Last updated: February 21, 2026