Made his debut as executive producer and also starred in "The Chase"
Formed production company Sheen-Michaels Entertainment with Bret Michaels, ex-lead singer of Poison
Reprised his role of Topper Harley in the sequel "Hot Shots! Part Deux"
Made TV movie acting debut in "Silence of the Heart" (CBS)
Acted in "Free Money" with Marlon Brando, Mira Sorvino and Donald Sutherland; aired on Starz! (filmed in 1997)
Acted with brother Emilio in "Men at Work"
Reprised role of 'Wild Thing' in the sequel "Major League II"
Starred in the sci-fi flick "The Arrival"
Played one of the titular swordsmen in "The Three Musketeers"
Received a star on the Hollywood Walk of Fame
Starred opposite Denise Richards in "Good Advice"; aired on HBO in lieu of a theatrical release
Starred with brother Emilio Estevez in the Showtime movie "Rated X"
Acted with father and brother Ramon in "Cadence," Martin Sheen's directorial debut
Appeared in brother Emilio Estevez's directorial debut "Wisdom"
Cast with Owen Wilson and Morgan Freeman in "The Big Bounce"
Executive produced (also co-scripted with Bret Michaels) and starred with father in "No Code of Conduct"; aired on USA Network
Landed a featured role in "Young Guns"
Launched a children's clothing line called Sheen Kidz
Scored big as pilot Topper Harley in the comedy spoof "Hot Shots!"
Acted opposite Chris Tucker in "Money Talks"
Appeared in "No Day at the Beach," a WWII episode of Steven Spielberg's "Amazing Stories" (NBC)
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
Played title role in "A Glimpse Inside the Mind of Charles Swan III," directed by Roman Coppola
Played the president of the United States in Robert Rodriguez's "Machete Kills," credited under his birth name Carlos Estevez
Cast in breakthrough lead role in Oliver Stone's "Platoon"
Joined the fifth season of ABC's political sitcom "Spin City," replacing Michael J. Fox in the lead role
Landed first co-starring role in "The Boys Next Door"
Landed first film appearance as an extra in Francis Ford Coppola's "Apocalypse Now," again starring his father
Made feature acting debut in "Grizzly II - The Predator"
Played a baseball pitcher nicknamed 'Wild Thing' in "Major League"
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
Cast as womanizer Charlie Harper on CBS sitcom "Two and a Half Men"; fired from show March 2011 after several weeks of increasingly erratic behavior
Contributed to the ensemble cast of baseball drama "Eight Men Out" directed by John Sayles
Made first TV appearance at age nine in NBC movie "The Execution of Private Slovik"; project starred his father Martin Sheen
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
Co-starred in the misguided drama "9/11," about the September 11, 2001 terrorist attacks