Jon Cryer and Ashton Kutcher in Two and a Half Men (2003)

Charlie Sheen, Jon Cryer, and Angus T. Jones in Two and a Half Men (2003)

Charlie Sheen and Jon Cryer in Two and a Half Men (2003)

Jon Cryer and Conan O'Brien in Conan (2010)

Charlie Sheen and Jon Cryer in Conan (2010)

Jon Cryer and Ashton Kutcher in Conan (2010)

Andrew McCarthy and Jon Cryer in Brats (2024)

John Hughes, Andrew McCarthy, and Jon Cryer in Brats (2024)

Jon Cryer, Donald Faison, Abigail Spencer, Sofia Capanna, and Finn Sweeney in Extended Family (2023)

Jon Cryer, Donald Faison, and Abigail Spencer in Extended Family (2023)

Jon Cryer in Superman IV: The Quest for Peace (1987)

Molly Ringwald, Jon Cryer, and Annie Potts in Pretty in Pink (1986)

Molly Ringwald, Andrew McCarthy, and Jon Cryer in Pretty in Pink (1986)

Jon Cryer and Harry Dean Stanton in Pretty in Pink (1986)

Demi Moore and Jon Cryer in No Small Affair (1984)

Gene Hackman, Mariel Hemingway, Jon Cryer, Christopher Reeve, Jackie Cooper, and Margot Kidder in Superman IV: The Quest for Peace (1987)