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 in Hot Shots! Part Deux (1993)

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

Charlie Sheen, Leo Geter, Tom Hodges, Ray 'Boom Boom' Mancini, Philip McKeon, Jed Mills, Ralph Seymour, and Larry Spinak in Amazing Stories (1985)

Charlie Sheen and Jennifer Grey in Ferris Bueller's Day Off (1986)

Charlie Sheen and Izabella Miko in Anger Management (2012)

Charlie Sheen and Derek Richardson in Anger Management (2012)

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, Jon Cryer, and Angus T. Jones 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 and Mare Winningham in Bad Day on the Block (1997)

Charlie Sheen and Emilio Estevez in Rated X (2000)

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

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 Chris Tucker in Money Talks (1997)

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)