Jimmy Buffett Was Your Favorite Country Singer’s Biggest Influence

The Outlaws’ legacy isn’t going anywhere, but the sound of the past two decades was tiki bars, beaches, and Buffett

Today’s country artists love to namecheck icons like Hank Williams, Johnny Cash, and Waylon Jennings in their songs and during interviews. But sonically, they owe their greatest debt to Jimmy Buffett, whose tropical vibes, beachy imagery, and ocean escapism has shaped the last two decades of mainstream country. Buffett died Friday at 76, leaving an undeniable legacy that is still heard in the songs of country radio and warrants future induction into the Country Music Hall of Fame.

While artists like Garth Brooks were mining bits of the tiki-bar sound with songs like “Two Piña Coladas” in the late Nineties, the Buffett big bang in country music can be traced roughly to 2002 with Kenny Chesney’s No Shoes, No Shirt, No Problems. After first nodding to Buffett a few years earlier in a verse of 1999’s “How Forever Feels,” Chesney buried his feet deep in the sand with the title track of No Shoes, No Shirt, No Problems, a 9-to-5 daydream about blowing off work, charting a course for Mexico, and packing “tank tops and flip-flops, if you got ‘em.” (If not? See the song’s title.)

“No Shoes” altered the trajectory of Chesney’s career and speeded his transformation from a “She Thinks My Tractor’s Sexy” country boy to the Caribbean cowboy he would become on albums like When the Sun Goes Down, Lucky Old Sun, and Hemingway’s Whiskey. His success in introducing Buffett’s island attitude to country music helped spawn a crush of similarly sunny hits: Blake Shelton’s “Some Beach,” Toby Keith’s “Stays in Mexico,” Zac Brown Band’s “Toes,” Billy Currington’s “People Are Crazy,” Sugarland’s “All I Wanna Do,” Dierks Bentley’s “Somewhere on a Beach,” Little Big Town’s “Day Drinkin’,” Luke Bryan’s “One Margarita,” Old Dominion’s “I Was on a Boat That Day,” the entire catalog of Jake Owen, and on and on.

But none of those exist without Jimmy Buffett.

“Jimmy painted pictures and short stories in all the songs he wrote,” Chesney said in a statement to RS. “He taught a lot of people about the poetry in just living, especially this kid from East Tennessee.”

That a songwriter born on the Gulf Coast in Pascagoula, Mississippi, could have such an impact on landlocked country singers — like Chesney from Tennessee, Keith and Shelton from Oklahoma, Brown and Bryan from Georgia — was apparent in the hours after Buffett died. Along with tributes from Paul McCartney, James Taylor, and President Biden, there were reams of messages and remembrances from mainstream country artists, all of them bowing to the king Parrothead’s impact.

Chesney posted a pre-dawn video of himself singing Buffett’s “A Pirate Looks at Forty” on an island. “The pirate has passed,” Keith tweeted. “Tremendous influence on so many of us.” Old Dominion thanked him for “providing countless musicians like us a comfortable, welcoming place to create our own music.” And Sugarland’s Kristian Bush acknowledged Buffett’s overt effect on his boozy new EP of tiki songs, Drink Happy Thoughts.

But Buffett’s sway wasn’t just tangential. Around the same time as Chesney’s “No Shoes, No Shirt, No Problems,” he made his own appearance on country radio by guesting on Alan Jackson’s escapist singalong, “It’s Five O’Clock Somewhere,” a monster Number One hit that earned Buffett his first CMA Award, for Vocal Event of the Year in 2003. While Buffett was a Nashville presence back in the Seventies — the first artist to play historic club Exit/In in 1971 — he was now fully in the Music Row orbit.

A year after the “Five O’Clock Somewhere” juggernaut, Buffett released a proper country album on RCA Nashville, License to Chill. Chesney, Jackson, and Keith all guested, along with George Strait and Clint Black, and it topped the country charts. He followed it up in 2006 with Take the Weather with You, another country chart-topper led by the radio single “Bama Breeze” that was written not by Buffett, but by Music Row heavyweights Mark Irwin, Josh Kear, and Chris Tompkins. The video, with Buffett strumming his guitar in a dilapidated Gulf Coast saloon, was in heavy rotation on CMT.

In 2011, he teamed with Zac Brown Band for “Knee Deep,” his second appearance on a country-radio hit. The year before, ZBB and Buffett played Buffett gems like “Son of a Son of a Sailor,” “A Pirate Looks at Forty,” and “Margaritaville” for an episode of CMT’s live-music series Crossroads. “Hope you’re knee deep in the water somewhere in paradise today,” Brown posted Saturday after Buffett’s death, and paid further tribute to him with a cover of “Margaritaville” at a concert that night in New Hampshire.

Yet for all of Buffett’s influence on contemporary country music, there’s something missing in many of the songs that he inspired when compared to his own work. Yes, the tropical sound is as noticeable as a sunburn and the living-for-the-moment messaging is as bold as a T-shirt slogan, but that extra layer of depth, introspection, and melancholy is often absent.

In “Come Monday,” Buffett poked holes in the gleaming hull of rock stardom, where all he wants is to be back with the one he left behind. In “He Went to Paris,” the old man at the center of the story-song survived a life well lived — but just barely. He ended up in the islands, fishing bridge pilings and drinking Johnnie Walker not out of leisure, but to dull the pain of losing his wife, his kid, and an eye. Even “Margaritaville,” the song that birthed a clothing line, a series of hotels, a chain of eateries, and a mindset, is deeper than the what-me-worry shorthand it has become: It’s a song of slowly realized blame and regret that can only be dulled by the tequila (without salt, no less!) that “helps me hang on.”

The narrator of “A Pirate Looks at Forty,” meanwhile, is consumed by taking stock of his four decades thus far, an existence of womanizing, drinking to oblivion, and literally sailing away from his problems. “Never meant to last,” Buffett repeats twice, to make sure we heard him. He wants us to fully grasp that everything is fleeting.

Chesney was one of those who got the message. While you may not hear it in some of his more breezy radio hits, he wove that Buffett melancholy throughout his 2005 masterwork Be as You Are (Songs From an Old Blue Chair), a collection of beach-centered songs all co-written by Chesney. It’s mainstream country’s best representation of the island life.

And none of it happens without Jimmy Buffett.