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Harrelson was born in Midland, Texas, the son of Diane Lou (née Oswald) and Charles Voyde Harrelson, who divorced in 1964; he has two brothers, Jordan and Brett, the latter of whom is a professional motorcycle racer. In 1979, in San Antonio, Federal Judge John Howland Wood was shot and killed by rifle fire by Charles Harrelson, who was a free-lance contract killer.[1] He was convicted and eventually died during his life sentence in maximum security prison. Harrelson grew up in Lebanon, Ohio, with his mother. Harrelson attended Lebanon High School and later Hanover College in Indiana, becoming a member of the Sigma Chi Fraternity, and receiving a Bachelor of Arts in Theater Arts and English in 1983.

After graduation, Harrelson moved to New York City. In 1985, he was cast as the naive but genial Midwestern bartender Woody Boyd on the classic television series Cheers, and won an Emmy for the role. His first film was 1986's Wildcats with Goldie Hawn. Harrelson became friends with Wesley Snipes and starred with him in the box-office hits White Men Can't Jump and Money Train. He appeared in mostly minor roles until he starred in Robert Redford's Indecent Proposal in 1993, a role which helped open doors for Harrelson in the film industry. In 1994 Harrelson starred in arguably his best known role to date, Mickey Knox in Oliver Stone's Natural Born Killers. During this time he also starred in the Farrelly brothers cult classic Kingpin. In 1996, he starred in the title role of the controversial film The People vs. Larry Flynt, for which he received a nomination for the Academy Award for Best Actor. Following this performance Harrelson went to star in films such as Wag the Dog, EDtv, The Thin Red Line and Palmetto. More recently, he had a fairly long run on the NBC sitcom Will & Grace as Grace's love interest Nathan and played FBI agent Stan in 2004's After the Sunset. His most recent films are A Prairie Home Companion, A Scanner Darkly, and No Country for Old Men which were released in June and July of 2006 and November of 2007, respectively.

In 1985, Harrelson married Nancy Simon, daughter of playwright Neil Simon, in Tijuana. The two intended to divorce the following day, but the storefront marriage/divorce parlor was closed when they had returned to it, and the two remained married for ten months. On January 11, 1998, Harrelson married Laura Louie, his former assistant of two years and a co-founder of Yoganics, an organic food delivery service. The couple, who have been together since 1990, have three daughters, Deni Montana (born February 28, 1993), Zoe Giordano (born September 22, 1996), and Makani Ravello (born June 3, 2006). When announcing Makani's birth, the couple referred to the three as their "goddess trilogy".

Harrelson is a supporter and activist for the legalization of marijuana and hemp in the US. On June 1, 1996, he was arrested in Kentucky after he symbolically planted four hemp seeds to challenge state law that failed to distinguish between industrial hemp and marijuana. Harrelson won the case. Harrelson is also an environmental activist. He once scaled the Golden Gate Bridge in San Francisco with members of North Coast Earth First! group to unfurl a banner that said, "Hurwitz. Aren't ancient redwoods more precious than gold?" in protest of PALCO CEO Charles Hurwitz, who once stated, "He who has the gold, makes the rules". Harrelson, an ethical vegan and raw foodist, has also denounced animal experiments in the cosmetics industry. He has travelled the American West Coast on a bike and domino caravan with a hemp oil-fueled biodiesel bus (the subject of the independent documentary, Go Further) and has narrated the documentary Grass. Harrelson briefly owned an oxygen bar in West Hollywood called "O2". He is also a peace activist and has often spoken publicly against the 2003 invasion of Iraq.