Jimmy Buffett’s 6 Best Country Collaborations

Music

During his career, the iconic singer-songwriter recorded with artists including Kenny Chesney, Alan Jackson and Martina McBride.

Jimmy Buffett of Jimmy Buffett and the Coral Reefer Band performs during the 2022 New Orleans & Jazz festival at Fair Grounds Race Course on May 8, 2022 in New Orleans, Louisiana.

Tim Mosenfelder/WireImage

Jimmy Buffett, the musical troubadour known for his island-tinged, rum-soaked hits including “Margaritaville,” “A Pirate Looks at Forty” and “Cheeseburger in Paradise,” as well as his empire of businesses including his chain of Margaritaville cafes, died on Friday (Sept. 1) at age 76.

“Jimmy passed away on the night of September 1st surrounded by his family, friends, music and dogs,” an early Saturday morning (Sept. 2) post on his official website read. “He lived his life like a song till the very last breath and will be missed beyond measure by so many.”

The Mississippi-born, Alabama-raised Buffett was a globally-known star, thanks to his carefree hits and colorful stage shows, but much of his musical roots ran through Nashville. In 2021, Buffett and his Coral Reefer Band played a private show at Exit/In — five decades after he made some of his first performances at the tiny club on Elliston Place in Music City. The club would serve as a launching pad for Buffett’s musical career, while Buffett and artists including Steve Martin would help Exit/In become one Nashville’s most venerable music clubs, thus helping to launch what would be known as the city’s historic “Rock Block,” alongside businesses including The End and The Gold Rush.

Buffett moved to Nashville in the late 1960s with ambitions of a career in country music. He became a Nashville reporter for Billboard from 1969-1970, where he is credited with breaking the news of the breakup of bluegrass duo Lester Flatt and Earl Scruggs in 1969. His tenure at Billboard was brief, due to the release of his 1970 debut album, Down to Earth.

His follow-up, 1973’s A White Sport Coat and a Pink Crustacean (the title is a twist on a Marty Robbins hit) was recorded at Tompall Glaser’s Nashville studio, which would later be dubbed “Hillbilly Central.” Though the album owed more to Nashville than the islands, listeners can hear beginnings of the Key West vibes Buffett would become known for. The album also testifies to Buffett’s impact as a songwriter; it includes the Buffett/Jerry Jeff Walker-written “Railroad Lady,” which was also recorded by artists including Lefty Frizzell, Merle Haggard and Willie Nelson. Waylon Jennings covered another of the album’s songs, “He Went to Paris,” on his 1980 album, Music Man, while Doug Supernaw recorded the track in 1994. Buffett would also co-write “Happiness Alone” with Clint Black, a song that appeared on Black’s album No Time to Kill.

The 1970s and 1980s saw several of Buffett’s songs rank on Billboard‘s country charts, including “The Great Filling Station Holdup” (1973), “Come Monday” (1974) and his star-making 1977 songs including “Changes in Latitude, Changes in Attitude” and “Margaritaville,” which would reach the top 10 on the Billboard Hot 100 chart, as well as No. 13 on the Hot Country Songs chart. He also earned a top 20 country hit in 1985 with “If The Phone Doesn’t Ring, It’s Me.”

During his five-plus decades in music, Buffett earned two No. 1 hits on Billboard‘s Hot Country Songs chart, as well as three top 10 hits, in part thanks to his willingness to maintain ties within the country music community, collaborating with a range of artists.

Buffett’s 2003 collaboration with Alan Jackson — “It’s Five O’Clock Somewhere,” about an overworked, underpaid blue collar worker who dreams of escaping to the islands — became an eight-week No. 1 Country Airplay hit. The song also reached the top 20 on the Hot 100. That same year, Kenny Chesney earned a major hit with the island-themed “No Shoes, No Shirt, No Problems,” further proving Buffett’s brand of island escapism was a key influence on the genre.

But even as far back as his 1998 hit “How Forever Feels,” Chesney paid homage to Buffett with the lyric, “Now I know how Jimmy Buffett Feels,” while the video’s tropical vibe helped cement cowboy hat-meets-puka shell necklace, “Island Kenny” persona Chesney would become known for in later songs and videos such as “When the Sun Goes Down.” Also in 1998, Garth Brooks also earned a hit with the tropical-themed “Two Pina Coladas,” a song written by Benita Hill, Shawn Camp and Sandy Mason; the writers had originally thought of pitching the song to Buffett, before it was ultimately pitched to Brooks. With songs like 2009’s “Toes,” “Jump Right In,” and their 2011 No. 1 hit collaboration with Buffett, “Knee Deep,” Zac Brown Band forged their own island jam band vibe.

“When contemporary country took it to the beach, obviously we were a big part of that,” Buffett told Billboard during a 2021 interview.

Notably, Buffett earned the sole Billboard 200-topping album of his career in 2004, with License to Chill, a collection of mostly country collaborations with artists including Chesney, George Strait, Clint Black, Martina McBride, Jackson and Toby Keith.

Chesney, who was a surprise guest during Buffett’s 2021 Exit/In show, paid tribute to Buffett on social media, stating, “So goodbye Jimmy. Thanks for your friendship and the songs I will carry in my heart forever. Sail On Sailor.” The two hitmakers previously collaborated on “Trying to Reason With Hurricane Season.”

“To me that song is true poetry, and a true reflection of Jimmy’s ability to tell a story and to capture a moment and to paint a picture of that moment,” Chesney later said in a video about the song. He added, “I’m not sure that Jimmy gets the credit that he deserves as being a poet, like a true songwriter, storyteller poet, a lot like [Ernest] Hemingway was in his time.”

Below, we look at some of Buffett’s top country collaborations:

“Too Drunk to Karaoke” (With Toby Keith)

Keith was featured on this Buffett track, included on Buffett’s 2013 album, Songs From St. Somewhere.

This humorous tale centers on a night spent at a packed karaoke bar. The popular nightspot has a long line of karaoke hopefuls, and as the evening lingers on and the margaritas keep flowing, soon the song’s intoxicated narrator makes his way to the stage.

“Don’t have to rehearse, or even sing on key/ Just prove that theory of drunketivity,” they sing.

“Trying to Reason With Hurricane Season” (With Kenny Chesney)

Two of music’s most islands-affiliated artists, Buffett and Chesney, united on this Buffett-written song, which Chesney included on his 2018 album, Songs for the Saints. The album itself, which also included Chesney collaborating with Ziggy Marley and Mindy Smith, was inspired by the aftermath of Hurricane Irma, which ravaged areas including The Virgin Islands, the Bahamas and Jamaica in 2017.

“Trip Around the Sun” (With Martina McBride)

In 2004, this collaboration reached No. 20 on the Country Airplay chart. The song was included on Buffett’s 2004 album, License to Chill, a collection of collaborations with scores of country artists, including Kenny Chesney, Alan Jackson, George Strait and Clint Black.

“Hey Good Lookin'” (With George Strait, Kenny Chesney, Toby Keith, Clint Black & Alan Jackson)

Another song from Buffett’s 2004 License to Chill album, this time he creates an mega-star collaboration, gathering Clint Black, Kenny Chesney, Alan Jackson, Toby Keith and George Strait for this rendition of a Hank Williams, Sr. classic. The License to Chill album drove Buffett to the top of the Billboard 200 albums chart for the first time in his career.

“Knee Deep” (With Zac Brown Band)

This 2011 hit reached No. 1 on Billboard‘s Hot Country Songs chart. In 2010, ZBB’w John Driskill Hopkins told Billboard that the Buffett collaboration came from a chance meeting in 2009.

“We met him on a camping trip last year,” Hopkins said, “and just sat around the fire with him for awhile. That was a quick friendship. He’s a real cat, really down to earth and doesn’t have a whole lot of ego and just a super nice guy…We did a lot of vocals down at his place in Key West and he happened to come through, so we got him to sit in and it sounded great. It sounds like a Buffett song when he sings it. Whatever he sings sounds like a Buffett song, y’know?”

“It’s Five O’Clock Somewhere” (With Alan Jackson)

Leading the charge of Buffett’s most well-known country collabs is his 2003 hit with Jackson, “It’s Five O’Clock Somewhere,” thanks to Jackson’s signature musical intro, “What would Jimmy Buffett do? The song spent eight weeks atop the Country Airplay chart and earned a CMA Award for vocal event of the year.

It wasn’t the first time Jackson and Buffett had collaborated together; in 1999, Jackson teamed with Buffett for a collaboration of “Margaritaville,” included on Jackson’s covers album Under the Influence. In the liner notes of the project, Jackson wrote, “I’ve always been a big Jimmy Buffett fan…I like his music and the fact that he does what he wants to do.”

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