Charlie Sheen and Maxwell Caulfield in The Boys Next Door (1985)

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)

John Cusack, Charlie Sheen, David Strathairn, and D.B. Sweeney in Eight Men Out (1988)

Charlie Sheen in Hot Shots! Part Deux (1993)

Nastassja Kinski and Charlie Sheen in Terminal Velocity (1994)

Charlie Sheen and Chris Tucker in Money Talks (1997)

Charlie Sheen and Michael Biehn in Navy Seals (1990)

Charlie Sheen, Corey Haim, and Kerri Green in Lucas (1986)

Charlie Sheen and Emilio Estevez in Badlands (1973)

Charlie Sheen and Sara Foster in The Big Bounce (2004)

Charlie Sheen and Ryan Stiles in Hot Shots! Part Deux (1993)

Charlie Sheen in Two and a Half Men (2003)

Charlie Sheen and Valeria Golino in Hot Shots! (1991)

Charlie Sheen in Grizzly II: Revenge (2020)

Charlie Sheen in Saturday Night Live (1975)

Charlie Sheen and Angie Harmon in Good Advice (2001)

Charlie Sheen and Jon Lovitz in Good Advice (2001)

Charlie Sheen and Denise Richards in Good Advice (2001)

Charlie Sheen and Lisa Kudrow in Friends (1994)

Charlie Sheen and Valeria Golino in Hot Shots! Part Deux (1993)

Charlie Sheen and Chris Kattan in Saturday Night Live: Cut for Time (2013)

Charlie Sheen and Mare Winningham in Bad Day on the Block (1997)

Charlie Sheen and Emilio Estevez in Rated X (2000)

Morgan Freeman, Charlie Sheen, Bruce Willis, Natasha Henstridge, Amanda Peet, Matthew Perry, Kevin Pollak, Ben Stiller, Snoop Dogg, and Owen Wilson in The Big Bounce (2004)

Charlie Sheen and Kristy Swanson in The Chase (1994)

Cary Elwes, Charlie Sheen, Valeria Golino, Lloyd Bridges, Queen Latifah, and Jimmy Fallon in Johnny Dangerously (1984)

Cary Elwes, Charlie Sheen, Valeria Golino, and Lloyd Bridges in Hot Shots! (1991)