- Was arrested in Columbus (Ohio) in June 1983, charged with disorderly conduct - he was dancing in the street, halting traffic; he later jumped out of a moving police van, laughing maniacally, and finally punched one of the two arresting officers to the ground.
- Father Charles Harrelson (Charles Voyde Harrelson), who was a hitman, was arrested in 1979 for killing Federal Judge John H. Wood Jr. in San Antonio, Texas.
- Big fan of Bill Murray. Bill appeared in Zombieland (2009) as a favor to Woody.
- A jury in Beattyville, Kentucky dismissed a marijuana possession charge against him. He was arrested in 1996 for planting 4 marijuana hemp seeds in rural Kentucky and in his defence he said he was challenging a state law that makes no distinction between marijuana and hemp, even though hemp contains little of the drug found in marijuana and can be used to make a variety of industrial products. (August 25, 2000)
- Both he and his Three Billboards Outside Ebbing, Missouri (2017)'s co-star Sam Rockwell were nominated for an Oscar for their performances and Harrelson voted for Rockwell over himself.
- Lovingly refers to his three daughters as the "Goddess trilogy".
- Close friend of Michael J. Fox.
- Activist for the legalization of marijuana.
- Maintains his residence on Hana in Maui, and his neighbors include Kris Kristofferson and Willie Nelson. The three have been known to play poker together.
- Good friends with the Red Hot Chili Peppers.
- He climbed the Golden Gate Bridge and put up a sign that read, "Hurwitz. Aren't ancient redwoods more precious than gold?" in protest of MAXXAM/Pacific Lumber CEO Charles Hurwitz, who once stated, "He who has the gold, makes the rules".
- His father was Charles Harrelson, a contract killer for the Mafia, who claimed, without evidence, to have participated in the assassination of President John F. Kennedy.
- Admits to having been a sex addict.
- Woody and approximately a dozen other hemp activists and environmentalists took a bicycle tour down the west coast of America, starting in Seattle, Washington and 1000 miles later ending at the University of Santa Barbara in California. The tour was escorted by the Mothership, a Chicago city transit bus fueled by hemp oil and powered by solar panels. The journey was documented in the film Go Further (2003). (April 2001)
- He has played the same character (Woody Boyd) in three different series: Cheers (1982), The Simpsons (1989) and Frasier (1993).
- Lives with Laura Louie and their children in Costa Rica. (2004)
- In 1991 he went to Nairobi, Kenya and lived in a tent on the outskirts of town for a few weeks to experience Africa and get away from it all.
- He is the first and, as of 2005, only regular cast member from Cheers (1982) to receive a nomination for an Academy Award.
- Was cast in Benny and Joon but dropped out to do Indecent Proposal and because he dropped out so did Laura Dern.
- As of 2023, he has been in 4 films that were Oscar-nominated for Best Picture: The Thin Red Line (1998), No Country for Old Men (2007), Three Billboards Outside Ebbing, Missouri (2017), and Triangle of Sadness (2022). No Country for Old Men is a winner in the category.
- Wanted to play Jake Brigance in A Time to Kill (1996), but author John Grisham objected to his casting.
- His friends Darius Rucker, Mark Bryan, Dean Felber and Jim 'Soni' Sonefeld of the rock band Hootie & the Blowfish wrote the song "Woody" about him. The number can be found on the group's eponymous 2003 album.
- Friend of Owen Wilson.
- Is the owner of an oxygen bar in West Hollywood, California. (2001)
- Claims to have had 17 jobs in one year.
- Is close friends with Wesley Snipes.
- Moonlights as the lead singer in the band Manly Moondog and the Three Kool Hats.
- Has three daughters with Laura Louie: Denni Harrelson (b. February 26, 1993), Zoe Harrelson (b. September 22, 1996) and Makani Harrelson (b. June 3, 2006).
- Was considered for the role of Lester Burnham in American Beauty (1999).
- Graduated from Hanover College in 1983 with a degree in theatre arts & English. Member Sigma Chi fraternity.
- He and Nancy Simon were married in Tijuana, Mexico.
- The ex-son-in-law of playwright Neil Simon, one of Woody's first plays was Simon's "Biloxi Blues" in 1984.
- He became co-owner of the boutique organic hotel Inn at the Black Olive located in Baltimore, Maryland.
- Has worked with 8 directors who have won a Best Director Oscar: James L. Brooks, Oliver Stone, Michael Cimino, Milos Forman, Barry Levinson, Ron Howard, and Joel Coen & Ethan Coen.
- Was married to Neil Simon's daughter, Nancy Simon. Has had relationships with: Carol Kane, Ally Sheedy and Moon Unit Zappa.
- The longest he has gone without an Oscar nomination is the 13 years between The People vs. Larry Flynt (1996) and The Messenger (2009).
- He is on the board of the directors for the Ex'pression Center For New Media, an art school in Emeryville, California.
- Shares the same birthday (July 23rd) with his "Hunger Games" film series co-star Philip Seymour Hoffman.
- He was inducted into the Texas Film Hall of Fame in March 2003 in Austin, Texas.
- Attended Indiana's Hanover College with U.S. Vice President Mike Pence.
- Chosen by People magazine as one of the 50 Most Beautiful People. (1990)
- His ancestry includes English, Scottish, German, and distant Dutch and Welsh.
- Was sued by MGM for dropping out of playing the brother in 'Benny and June' when he was offered 'Indecent Proposal'.
- He considers Howard Zinn to be a personal hero of his.
- Brother of Brett Harrelson and Jordan Harrelson.
- Was set to star in the Danny Boyle's firefighter drama "Worcester Cold Storage" with Ed Harris, but the project never came to fruition.
- Was a singer with the group Madly Moondog and the Three Kool Kats.
- Roomed with good friend Rob Moran in New York when both were starting out.
- Attended the 2009 Comic-Con International in San Diego, California. (July 2009)
- Along with Owen Wilson, he attended the Sony Ericsson Open in Key Biscayne, Florida on April 5th. (April 2008)
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