When Woody Harrelson was 11 he wrote his first song, the subtly politically slanted “Better World.” Before his big break on Cheers in 1985, Harrelson was still connected to music and performing and was even cast in Neil Simon’s Broadway production of Biloxi Blues, starring Matthew Broderick, as a standby.
“Once I became this famous TV guy, I didn’t know how to go about being a musician again,” said Harrelson in a 1991 interview. He added “Music was always something I wanted to do. It’s always been cooking right below the surface.”
By the time Cheers ended its successful 11-year run on television and Harrelson had packed up his sweetly naïve character of Woody Boyd, he had already started exploring music and formed Manly Moondog and the Three Kool Kats. Fronting the group along with a team of musicians (the Kool Kats), Harrelson along with songwriting partner and guitarist Alphons Kettner, never released an album with the band but wrote enough songs to take them on the road in the early ’90s.
Throughout the decades, Harrelson slipped back into music and contributed to some of his film scores, singing several songs, including “Whoop-I-Ti-Yi-Yo,” and “Bad Jokes,” for the soundtrack to the 2006 musical comedy A Prairie Home Companion, also starring Meryl Streep and Tommy Lee Jones, along with a cover of Elvis Presley‘s 1972 “Burning Love” for his 2009 apocalyptic comedy Zombieland.
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His collaborations also span work with artists including Darius Rucker, Lenny Kravitz, Ziggy Marley, and more. He can even be heard reading a verse from the bible at the beginning of The Killers‘ Wonderful Wonderful track “The Calling.”
Harrelson has had a dynamic relationship with music throughout his career, in film, television, musical collaborations, and as a songwriter.
Though much isn’t known about the Manly Moondog era—or Harrelson’s revamp of his earliest song “Better World”—here’s a look at two songs he wrote during the ’90s with the band and another pair he collaborated on with other artists in the ’00s and 2010s.
1. “Celebrate Yourself” (1992)
Manly Moondog and the Three Kool Kats’ song “Celebrate Yourself” was inspired by 19th-century poet Walt Whitman. When introducing the song during an Amnesty International benefit concert that aired on the Lifetime network in 1992, Harrelson references Whitman’s 1855 poem Song of Myself.
“I’m a big fan of Walt Whitman who wrote ‘I celebrate myself, and sing myself,'” said Harrelson, “and sometimes I feel like we forget to celebrate ourself. We can love our neighbors sometimes, but do we love ourselves? … I wrote this little song. It’s called ‘Celebrate Yourself.'”
We’ve all been anointed / We’ve all been dethroned / On days like these I, I miss the boy I used to know sings Harrelson on the Caribbean-tinged song.
2. “Inside and Out” (1992)
“I’ve had a kind of metamorphosis in my life, from the more material, physical to the spiritual,” said Harrelson to a crowd during one of the band’s 1992 shows. “But some of the old songs still exist, and this song represents more of the physical aspects of my life.”
In the song, Harrelson sings about going to see the Grateful Dead, and his more libertine ways: I’ve had so many lovers but I don’t know what love’s about.
3. “Hold On,” Darius Rucker (2002)
Shortly after Hootie & the Blowfish released their third album, Musical Chairs, in 1998, Darius Rucker went to work on his debut solo album. Released in 2002, Back to Then features a collection of co-writers and special guests, including Snoop Dogg on the closing “Sleeping in My Bed.”
Harrelson also joined Rucker, and provided backing vocals on the track “Hold On,” but their friendship stretches beyond their musical collaboration. In 2014, Rucker shared a story about how Harrelson once saved him from drowning in a rough current in Hawaii.
“I’m in Hawaii with him [Harrelson] hanging out at his place, and we decided to go swimming,” shared Rucker. “We jump in the water—and I’m used to East Coast beaches with the beach right there—so we jump in the water, and all I can nothing but fish and there’s no bottom. So I start to freak out and I get caught in this current that’s taking me to the rocks.”
Rucker continued, “All of a sudden, here’s Woody Harrelson, and I’m telling you he literally saved my life. At one point we got so tired I said ‘Hey man, just let me go. I’m good,’ and he said ‘Not on my watch, man.’ We struggled for an hour and he got me out of that water. … I owe him a lot. He’s my guy. I love him.”
4. “Wild and Free,” Ziggy Marley (2011)
Harrelson duets with Ziggy Marley on the title track of the reggae artist’s fourth solo album. Written as a pro-marijuana song, “Wild and Free” was written by Marley and Harrelson in support of the Proposition 19 campaign in California to legalize recreational marijuana, which was eventually legalized in the state in 2016.
“I wanted a movement attached to the record, and the movement is the whole idea of using the cannabis plant for more than what it’s used for now,” said Marley of the song and the album, which largely promotes the free use of cannabis. “It can be used for environmental reasons, and industrial reasons, and nutritional reasons, to benefit the planet, not just for getting high.”
Photo: Gareth Cattermole/Getty Images
