Made first TV appearance at age nine in NBC movie "The Execution of Private Slovik"; project starred his father Martin Sheen
Produced and directed over 200 Super-8 and video film shorts, including 16mm "R.P.G."
Landed first film appearance as an extra in Francis Ford Coppola's "Apocalypse Now," which starred his father
Made film acting debut in "Grizzly II ¿ The Predator"
Made TV movie acting debut in "Silence of the Heart" (CBS)
Appeared in "No Day at the Beach," a WWII episode of Steven Spielberg's "Amazing Stories" (NBC)
Landed first co-starring role in "The Boys Next Door"
Cast in breakthrough lead role in Oliver Stone's "Platoon"
Appeared in brother Emilio Estevez's directorial debut "Wisdom"
Re-teamed with Oliver Stone for "Wall Street," playing Gordon Gekko's (Michael Douglas) protégé; also teamed with his father, who played his onscreen parent
Landed a featured role in "Young Guns"
Contributed to the fine ensemble of "Eight Men Out" directed by John Sayles
Played a baseball pitcher nicknamed 'Wild Thing' in "Major League"
Acted with brother Emilio in "Men at Work"
Scored big as pilot Topper Harley in the comedy spoof "Hot Shots!"
Acted with father and brother Ramon in "Cadence," Martin Sheen's directorial debut
Reprised his role of Topper Harley in the sequel "Hot Shots! Part Deux"
Received a star on the Hollywood Walk of Fame
Played one of the titular swordsmen in "The Three Musketeers"
Reprised role of 'Wild Thing' in the sequel "Major League II"
Made his debut as executive producer and also starred in "The Chase"
Starred in the sci-fi flick "The Arrival"
Acted opposite Chris Tucker in "Money Talks"
Formed production company Sheen-Michaels Entertainment with Bret Michaels, ex-lead singer of Poison
Acted in "Free Money" with Marlon Brando, Mira Sorvino and Donald Sutherland; aired on Starz! (filmed in 1997)
Executive produced (also co-scripted with Bret Michaels) and starred with father in "No Code of Conduct"; aired on USA Network
Starred with brother Emilio Estevez in the Showtime movie "Rated X"
Joined the fifth season of ABC's political sitcom "Spin City," replacing Michael J. Fox in the lead role
Starred opposite Denise Richards in "Good Advice"; aired on HBO in lieu of a theatrical release
Cast as womanizer Charlie Harper on CBS sitcom "Two and a Half Men"; received Golden Globe (2004, 2005), SAG (2004, 2009) and Emmy (2006, 2007, 2008, 2009) nominations for Best Actor in a Comedy Series; fired from show March 2011 after several weeks of increasingly erratic behavior
Cast with Owen Wilson and Morgan Freeman in "The Big Bounce"
Launched a children's clothing line called Sheen Kidz
Reprised his role of Bud Fox with a cameo in Oliver Stone's "Wall Street: Money Never Sleeps"
Cast in minor role in comedy "Due Date," starring Robert Downey Jr. and Zach Galifianakis
Launched "The Torpedo of Truth: Defeat is Not an Option" tour in Detroit, MI
Made series television comeback with starring role on "Anger Management" (FX) as a former baseball player whose anger issues lead him to become a therapist
Played title role in "A Glimpse Inside the Mind of Charles Swan III," directed by Roman Coppola