- 2009: Played Jennifer Aniston's yogurt mogul ex-boyfriend in the comedy, "Management"
- 2008: Cast opposite Will Ferrell in the 1970s-era sports comedy "Semi-Pro"
- 2008: Appeared as a blind pianist who befriends Will Smith's character in "Seven Pounds"
- 2007: Co-starred with Tommy Lee Jones and Javier Bardem in the Coen brothers' "No Country for Old Men"
- 2006: Starred in "A Scanner Darkly" a rotoscoped film by director Richard Linklater; adapted from the novel by Philip K. Dick
- 2006: Cast in Robert Altman's ensemble feature "A Prairie Home Companion," based on Garrison Keilor's radio program
- 2005: Cast opposite Julianne Moore in "The Prize Winner of Defiance Ohio" about a single mom who enters a commercial jingle-writing contest to support her ten children
- 2005: Played an idealistic lawyer in "North Country" a fictionalized account of the first major successful sexual harassment case in the United States
- 2004: Cast in the Spike Lee comedy "She Hate Me"
- 2004: Co-starred with Pierce Brosnan and Salma Hayek in "After the Sunset"
- 2003: Appeared opposite Adam Sandler and Jack Nicholson in "Anger Management" as Galaxia/Garry the Guard
- 2001: Acted in a four-episode story arc on "Will & Grace" (NBC), playing a love interest for Debra Messing's Grace
- 2000: Acted on stage opposite Nick Nolte and Sean Penn in "The Late Henry Moss" written by Sam Shepard
- 1999: Returned to Broadway as star of a revival of "The Rainmaker"
- 1999: Reprised character of Woody Boyd in an episode of "Frasier"; earned Emmy nomination as Outstanding Guest Actor in a Comedy Series
- 1999: Directed a revival of his stage play "Furthest From the Sun," starring Steve Guttenberg
- 1998: Had a high-profile cameo as Sergeant Keck in Terrence Malick's "The Thin Red Line"
- 1998: Portrayed a 1940s rancher in the contemporary Western "The Hi-Lo Country"
- 1997: Had supporting roles in "Welcome to Sarajevo" and "Wag the Dog"
- 1996: Earned a Best Actor Oscar nomination for his superb turn as magazine publisher Larry Flynt in "The People vs. Larry Flynt"; Stone was one of the producers
- 1995: Reteamed with Snipes for the disappointing "Money Train"
- 1994: Cast as one half of the murderous honeymoon team (with Juliette Lewis) in Oliver Stone's controversial "Natural Born Killers"
- 1993: Wrote, directed and acted in Los Angeles stage production, "Furthest From the Sun"
- 1993: Co-starred with Demi Moore and Robert Redford in "Indecent Proposal"
- 1992: Starred opposite Snipes in Ron Shelton's "White Men Can't Jump"
- 1991: Dropped as grand marshall of the New Orleans Mardi Gras parade and canned as a spokesman for the Miller Brewing Company for speaking out against the Gulf War
- 1991: First notable role in a theatrical feature, "Doc Hollywood"
- 1990: Formed own production company, Shepwood Productions
- 1988: Appeared off-Broadway in "The Boys Next Door"
- 1987: TV-movie debut, "Bay Coven" (NBC)
- 1986: Film debut, "Wildcats" opposite Goldie Hawn; first film with Wesley Snipes who also made his film debut
- 1985: TV series debut as Woody Boyd on "Cheers" (NBC); received five consecutive Emmy Award nominations (1987-1991) and won in 1989
- 1985: Understudied two roles, Roy Selridge and Joseph Wykowski, in the Broadway production of Neil Simon's "Biloxi Blues"
- 1983: Moved to New York City after graduating from college
- 1968: Father sent to prison for a contract killing
- Appeared in more than 25 plays at Hanover College
- Deemed dyslexic, hyperactive and psychologically disturbed as a child
- Moved with mother and brothers to Lebanon, OH
- Dropped by agent after becoming belligerent following an unsuccessful soap opera audition
- Mounted his own play, "2 on 2" (on the subject of basketball) with Edward Albee's "The Zoo Story" in Hollywood
- Father released after his sentence was reduced
- Began drinking heavily and getting into fights
- Born in Midland, Texas
- Placed in a school for children with behavioral problems; became deeply religious like his mother
- Father sentenced to life imprisonment for the contract killing of a federal judge while Harrelson was in college
- Reportedly had 17 jobs in one year
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