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)

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

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)

Molly Ringwald and Jon Cryer in Pretty in Pink (1986)

Andrew McCarthy and Jon Cryer in Brats (2024)

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

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)