Best Jon Cryer Movies & TV Shows

The 22 best movies and shows starring Jon Cryer, ranked by weighted audience score on 3eyedraven — their strongest work first. Each includes cast, ratings, trailers and where to watch.

Two and a Half Men 2003 ★ 7.5

Big Time Adolescence 2020 ★ 7.2

aka Charlie Sheen 2025 ★ 7.5

Pretty in Pink 1986 ★ 6.7

Company 2011 ★ 6.9

Hot Shots! 1991 ★ 6.6

BRATS 2024 ★ 6.0

Cannes Man 1996 ★ 5.5

Dudes 1987 ★ 5.7

Hiding Out 1987 ★ 5.7

Penn & Teller Get Killed 1989 ★ 5.6

Unstable Fables: 3 Pigs and a Baby 2008 ★ 5.8

Morgan Stewart's Coming Home 1987 ★ 5.1

Weather Girl 2009 ★ 5.6

Shorts 2009 ★ 5.9

No Small Affair 1984 ★ 5.5

Tortured 2008 ★ 5.5

O.C. and Stiggs 1987 ★ 4.5

Stay Cool 2011 ★ 4.8

Holy Man 1998 ★ 5.2

Ass Backwards 2013 ★ 4.4

Superman IV: The Quest for Peace 1987 ★ 4.6