Gene Hackman, Jon Cryer, and Christopher Reeve in Superman IV: The Quest for Peace (1987)

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

Jon Cryer, Leslie Mann, and Kat Dennings in Shorts (2009)

Mimi Rogers, Jon Cryer, Ashton Kutcher, Judy Greer, and Sophie Winkleman in Two and a Half Men (2003)

Jon Cryer and Sophie Winkleman in Two and a Half Men (2003)

Jon Cryer, Ashton Kutcher, Judy Greer, and Sophie Winkleman in Two and a Half Men (2003)

Jon Cryer and Judy Greer in Two and a Half Men (2003)

Mimi Rogers, Jon Cryer, and Judy Greer in Two and a Half Men (2003)

Jon Cryer, Ashton Kutcher, Angus T. Jones, and Sophie Winkleman in Two and a Half Men (2003)

Mimi Rogers and Jon Cryer in Two and a Half Men (2003)

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

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

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

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)

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

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)