Best known for playing Alan Harper on Two and a Half Men (CBS, 2003-2015, 12 seasons) and Duckie Dale in Pretty in Pink (1986); also notable for The Trouble with Normal and extended voice work.
Films
- Hit by a BusDan2024
- The Big BangRoger2021
- Tales of an Ancient EmpirePrince Aedan2010
- The Nate and Margaret Show(voice) Nathan2009
- Devil’s ArithmeticAaron1999
- Hot Shots! Part DeuxJim ‘Wash’ Washington1993
- Hiding OutAndrew Morenski / Max Hauser1987
- Pretty in PinkPhilip F. ‘Duckie’ Dale1986
- No Small AffairCharles Cummings1984
TV shows
- The DropoutDr. John D. at Gwyneth Paltrow’s ski resort (cameo)2022
- SupergirlLex Luthor (3 episodes)2016
- Two and a Half MenAlan Harper (262 episodes)2003
- The Trouble with NormalZach Mango (13 episodes)2000
- PartnersBob (2 episodes)1996
- The Famous Teddy ZTeddy Zakalokis (20 episodes)1989
- Head of the ClassAlan Pinkard (1 episode)1986
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About Jon Cryer
Jon Cryer is an American actor, comedian, and producer who rose to fame in the 1980s with his iconic role as Duckie in Pretty in Pink. He achieved massive television success as Alan Harper on the sitcom Two and a Half Men, earning two Primetime Emmy Awards. Beyond acting, Cryer has directed and produced, and remains active in television and film.
FAQs
What is Jon Cryer’s most famous role?
His most famous role is Alan Harper on the CBS sitcom ‘Two and a Half Men’, which he played for 12 seasons (2003-2015).
Has Jon Cryer won any awards?
Yes, he won two Primetime Emmy Awards for Outstanding Supporting Actor in a Comedy Series for his work on ‘Two and a Half Men’ in 2009 and 2012.
Did Jon Cryer appear in the Arrowverse?
Yes, he played Lex Luthor in the TV series ‘Supergirl’ (2016) and later reprised the role in a crossover event.
What was Jon Cryer’s first major film role?
His first major film role was as Charles Cummings in ‘No Small Affair’ (1984), but his breakthrough was as Duckie in ‘Pretty in Pink’ (1986).
Is Jon Cryer also a director or producer?
Yes, he has directed episodes of ‘Two and a Half Men’ and other series, and also produced the sitcom ‘The Trouble with Normal’.
Sources & where to watch: IMDb · Wikipedia · Where to watch (JustWatch UK) · Updated June 2026