- 2009: Nominated for the 2009 Primetime Emmy Award for Outstanding Lead Actor in Comedy Series
- 2009: Nominated for the 2009 Teen Choice Award for Choice TV Actor: Comedy
- 2006: Launched clothing line for kids, called Sheen Kidz
- 2004: Cast with Owen Wilson and Morgan Freeman in "The Big Bounce"
- 2003: Cast as Charlie Harper in the CBS sitcom, "Two and a Half Men"; received Golden Globe (2004, 2005), SAG (2005) and Emmy (2006, 2007, 2008, 2009) nominations for Best Actor in a Comedy Series
- 2001: Starred opposite Denise Richards in "Good Advice"; aired on HBO in lieu of a theatrical release
- 2000: Joined the fifth season of ABC's political sitcom, "Spin City," replacing Michael J. Fox in the lead role
- 2000: Starred with brother, Emilio Estevez in the Showtime movie, "Rated X"
- 2000: Executive produced (also co-scripted with Michaels) and starred with father in "No Code of Conduct"; aired on USA Network
- 1999: Acted in "Free Money" with Marlon Brando, Mira Sorvino and Donald Sutherland; aired on Starz! (filmed in 1997)
- 1997: Acted opposite Chris Tucker in "Money Talks"
- 1996: Had lead role in the sci-fi flick "The Arrival"
- 1994: Again played 'Wild Thing' in sequel "Major League II"
- 1994: Debut as executive producer (also starred), "The Chase"
- 1993: Received a star on the Hollywood Walk of Fame
- 1993: Played one of the titular swordsmen in "The Three Musketeers"
- 1993: Reprised his role of Topper Harley in the sequel "Hot Shots! Part Deux"
- 1991: Scored big as pilot Topper Harley in the comedy spoof, "Hot Shots!"
- 1991: Acted with father and brother Ramon in "Cadence"; Martin Sheen's directorial debut
- 1990: Acted with brother Emilio in "Men at Work"
- 1989: Played a baseball pitcher nicknamed 'Wild Thing' in "Major League"
- 1988: Had featured role in "Young Guns"
- 1988: Contributed to the fine ensemble of "Eight Men Out" directed by John Sayles
- 1987: Re-teamed with Oliver Stone for "Wall Street"; also teamed with his father, who played his onscreen parent
- 1986: Appeared in brother Emilio Estevez's directorial debut "Wisdom"
- 1986: Breakthrough lead role, Oliver Stone's "Platoon"
- 1985: Appeared in "No Day at the Beach," a WWII episode of Steven Spielberg's "Amazing Stories" (NBC)
- 1985: First co-starring role, "The Boys Next Door"
- 1984: TV-movie acting debut, "Silence of the Heart" (CBS)
- 1984: Film acting debut, "Grizzly II - The Predator"
- 1979: First film appearance, an extra in Francis Ford Coppola's "Apocalypse Now" starring his father, Martin Sheen
- 1974: First TV appearance, at age nine, in the NBC TV-movie, "The Execution of Private Slovik" starring his father, Martin Sheen
- Produced and directed over 200 Super-8 and video film shorts, including the 16mm "R.P.G."
- Formed production company Sheen-Michaels Entertainment with Bret Michaels, ex-lead singer of Poison
- Wrote, produced and directed 35mm short, "R.P.G. II"
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