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01
He was arrested in Columbus, Ohio in June 1983 for disorderly conduct after dancing in the street; he later jumped out of a moving police van and punched an arresting officer.
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02
His father Charles Harrelson was a hitman arrested in 1979 for killing Federal Judge John H. Wood Jr. in San Antonio, Texas.
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03
He is a big fan of Bill Murray, who appeared in Zombieland 2009 as a favor to him.
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04
Both he and his Three Billboards Outside Ebbing, Missouri 2017 co-star Sam Rockwell were nominated for an Oscar, and Harrelson voted for Rockwell over himself.
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05
A jury in Beattyville, Kentucky dismissed a marijuana possession charge against him after his 1996 arrest for planting four hemp seeds in rural Kentucky.
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06
He is a close friend of Michael J. Fox.
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07
He lovingly refers to his three daughters as the Goddess trilogy.
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08
He maintains a residence on Hana in Maui, where neighbors include Kris Kristofferson and Willie Nelson; the three have been known to play poker together.
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09
He is an activist for the legalization of marijuana.
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10
He climbed the Golden Gate Bridge and put up a sign protesting MAXXAM/Pacific Lumber CEO Charles Hurwitz, reading, ‘Hurwitz. Aren’t ancient redwoods more precious than gold?
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11
He is good friends with the Red Hot Chili Peppers.
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12
His father, Charles Harrelson, a contract killer for the Mafia, claimed without evidence to have participated in the assassination of President John F. Kennedy.
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13
He admits to having been a sex addict.
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14
He has played the same character Woody Boyd in three different series: Cheers 1982, The Simpsons 1989 and Frasier 1993.
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15
Woody and about a dozen hemp activists and environmentalists took a bicycle tour down the west coast, starting in Seattle and ending at the University of Santa Barbara, documented in the film Go Further 2003.
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16
He is the first and, as of 2005, only regular cast member from Cheers 1982 to receive an Academy Award nomination.
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17
He lives with Laura Louie and their children in Costa Rica.
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18
In 1991 he went to Nairobi, Kenya and lived in a tent on the outskirts of town for a few weeks to experience Africa.
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19
He wanted to play Jake Brigance in A Time to Kill 1996 but author John Grisham objected to his casting.
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20
He was cast in Benny and Joon but dropped out to do Indecent Proposal, causing Laura Dern to also leave the project.
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21
He is a friend of Owen Wilson.
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22
His friends Darius Rucker, Mark Bryan, Dean Felber and Jim Sonefeld of Hootie & the Blowfish wrote the song Woody about him, on their 2003 album.
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23
He is close friends with Wesley Snipes.
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24
He moonlights as the lead singer in the band Manly Moondog and the Three Kool Hats.
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25
He has appeared in four films 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 won.
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26
He claims to have had 17 jobs in one year.
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27
He has three daughters with Laura Louie: Denni b. February 26, 1993, Zoe b. September 22, 1996 and Makani b. June 3, 2006.
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28
He was considered for the role of Lester Burnham in American Beauty 1999.
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29
He and Nancy Simon were married in Tijuana, Mexico.
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30
He became co-owner of the boutique organic hotel Inn at the Black Olive in Baltimore, Maryland.
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31
He is the owner of an oxygen bar in West Hollywood, California.
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32
He graduated from Hanover College in 1983 with a degree in theatre arts and English, and was a member of Sigma Chi fraternity.
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33
He was the ex-son-in-law of playwright Neil Simon; one of his first plays was Simon’s Biloxi Blues in 1984.
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34
He was married to Neil Simon’s daughter Nancy Simon, and has had relationships with Carol Kane, Ally Sheedy and Moon Unit Zappa.
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35
He has worked with eight directors who have won Best Director Oscars: James L. Brooks, Oliver Stone, Michael Cimino, Miloš Forman, Barry Levinson, Ron Howard, and Joel and Ethan Coen.
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36
He shares the same birthday July 23 with his Hunger Games co-star Philip Seymour Hoffman.
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37
He was inducted into the Texas Film Hall of Fame in March 2003 in Austin, Texas.
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38
The longest gap between his Oscar nominations is 13 years between The People vs. Larry Flynt in 1996 and The Messenger in 2009.
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39
He serves on the board of directors for the Ex’pression Center For New Media in Emeryville, California.
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40
He was chosen by People magazine as one of the 50 Most Beautiful People.
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41
His ancestry includes English, Scottish, German, and distant Dutch and Welsh.
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42
He was sued by MGM for dropping out of Benny and Joon to take the role in Indecent Proposal.
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43
He attended Hanover College with U.S. Vice President Mike Pence.
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44
He considers historian Howard Zinn a personal hero.
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45
One of his films, No Country for Old Men 2007, has been selected for the National Film Registry by the Library of Congress.
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46
He roomed with friend Rob Moran in New York when both were starting out.
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47
He is brother to Brett Harrelson and Jordan Harrelson.
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48
He was set to star in Danny Boyle’s firefighter drama Worcester Cold Storage with Ed Harris, but the project never materialized.
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49
He was a singer with the group Madly Moondog and the Three Kool Kats.
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50
He attended the 2009 Comic-Con International in San Diego, California.