Jimmy Buffett: 15 Essential Songs

See that 86-year-old guy fishing, drinking and chilling out near the water? He seems fairly average, at least until you hear his story. Looking for adventure, he moved first to France and then England, met his life partner, had a baby and then lost it all, including one of his eyes, in the war. (We’ll presume World War II, but it’s not specified.) One of Buffett’s most harrowing and poignant story songs, this track from his album A White Sport Coat and a Pink Crustacean revealed early on that there could be unexpected depth beneath Buffett’s good-time persona. —D.B.

The opening track to 1973’s A White Sport Coat and a Pink Crustacean is a story-song about knocking over a gas station for 15 bucks, a can of motor oil, a jar of cashews, and a TV. It’s not exactly the Lufthansa heist, but Buffett and his pellet-gun-wielding accomplice celebrate it as such with one too many beers. Their drunken party ends with the cops showing up to rough ‘em, cuff ‘em, and toss them in the can. It’s a lighthearted romp, but stands as a prime example of the wry wit that Buffett would perfect in the years to come.  —J.H.

If there was ever a hint of a dark side to Buffett’s work, it could be found in this concert standard from his fifth album, A1A. The narrator, based on a real-life Buffett pal named Phil Clark, arrives at middle age looking back on a life of drug smuggling, drinking, and chasing women. Those days are gone: “I made enough money to buy Miami, but I pissed it away so fast,” Buffett sings. But the song is ultimately about wisdom and resilience, reflecting with a sense of loss but not regret, and Buffett makes the tale go down easy with an island-breeze melody that conveys a what-me-worry beach lifestyle before it all went south. — D.B.

At a time when most of his fellow singer-songwriters were relentlessly downcast and introspective, Buffett could display a lighter, more puckish touch; in other words, the dude had a sense of humor. Part of 1976’s Havana Daydreamin’, “My Head Hurts …” could easily be a country song: The narrator winds up in a bar, listening to Merle Haggard records, before hooking up with a fellow customer and waking up at her place, hungover, the next morning. From the use of the word “Darvon” (not a product you’d hear about in a country tune) to the intentionally corny countrypolitan backup choir in the arrangement, Buffett revels in country cliches and tweaks them at the same delicious time. —D.B.

The song that launched an empire, from a resort chain to a short-lived Broadway musical, is at its core a bit of a downer. The narrator is apparently alone near the beach, watching tourists and bumming over a relationship gone wrong. And let’s not forget the cut heel, the lost condiments and the “frozen concoctions that help me hang on.” As Buffett himself told RS in 2107, “There was a melancholy to Key West, and there is a melancholy to people who are escaping.” But there’s a reason “Margaritaville,” which Buffett said he wrote in five minutes at an airport, transcends its story and became his best-known and most loved song. The chorus instantly lodges in your brain, the song overall has a rakish charm, and you just have to root for the guy, who goes from admitting “it’s nobody’s fault” in the first chorus to “I know it’s my own damn fault” in the last. He may be a slacker, but at least he’s self-aware. —D.B.

Folk singer-songwriter Steve Goodman wrote and recorded this song about American expats enjoying the fruits of imperialism in Latin America, “spending those renegade pesos/On a bottle of rum and a lime.” Buffett infused Goodman’s social critique with a warm ambivalence and an honest sense of identification, as if he might’ve had people he’d met personally when he sang lines like, “Some of them are running to lovers/Leaving no forward address/Some of them are running tons of ganja/Some are running from the IRS.” The song came out in 1977, the peak year of punk rock. Rock critics would soon be rushing to congratulate bands like the Clash and the Gang of Four for interrogating the ambiguities and contradictions of capitalism “from the inside.” Buffett does that perfectly here (not that too many critics were listening), and he does it with a shrug and smile and a slice of lime in your drink to go with it.— J.D.

The utterly charming title track of the album that also gave us “Margaritaville” mines a similar pop-calypso feel, but it’s less melancholy than the far bigger hit. There’s still plenty of drinking (rum and red wine) and much rueful longing over the adventures of the previous year. But while the narrator of “Margaritaville” seems a bit lost, this Buffett is more at peace with his escapades and run-ins, and its key line — “If we couldn’t  laugh, we would all go insane” — deftly summed up the appeal of Buffett’s music and image. — D.B.

Buffett crafted the ultimate tale of maritime wanderlust with the title track to his 1978 album. There are geographical references to Trinidad, a grocery aisle’s worth of allusions to Caribbean delicacies (chief among them, rum), and enough sailing jargon to fill a manual. But the song is defined by its honest-to-goodness faith in the unknown. “Where it all ends I can’t fathom my friends,” Buffet admits near the end, before dropping one of the best payoff lines of his entire catalog: “I’m just glad I don’t live in a trailer.”  —J.H.

It’s the song that birthed the Parrothead salute — the meeting of palms above the head every time Buffett shouts “Fins Up!” onstage and shimmying like a fish. Sure, it looks silly as hell, but it’s as fun as this 1979 anthem about a beautiful warm-weather transplant fending off the advances of those “sharks that can swim on the land.” Originally appearing on Buffett’s Volcano album, “Fins” isn’t just a song, it’s a literal movement. —J.H.

In anyone else’s hands, this song — a lovely pop ballad and Buffett’s first top 40 hit — would have been utterly unrelatable. Starting with its opening line, about heading to San Francisco for “the Labor Day weekend show,” it hints at the drudgery of the rock touring lifestyle and leaving a loved one behind. But as the narrator clings to the thought of a reunion with his partner, the song soon becomes far more universal than just another on-the-road ramble. In an early indication of the way Buffett could also connect with his fans, he admits upfront he isn’t cool: “I got my Hush Puppies on/I guess I never was meant for glitter rock & roll.” But he was meant for plenty of other things. — D.B.

Big Meat owes Buffett a heifer-sized debt of gratitude for all he did to promote burger eating. While vegans may recoil at a song that pines for something ordered “medium-rare with Muenster,” “Cheeseburger in Paradise” kicked into high gear the salivary glands of carnivores everywhere. It’s not just a novelty song either. Rather, it’s a Zen-like reminder to appreciate the simple things. Like Warren Zevon (whose songs Buffett covered live in concert) said, “Enjoy every sandwich.” —J.H.

While technically an Alan Jackson song that features Buffett, this happy hour singalong is inextricably linked to the king Parrothead. He made it a staple of his live shows and performed it more than a few times with the country singer, who in the recorded version tees up his guest with a lyric that belongs on a T-shirt: “What would Jimmy Buffett do?” Enter Buffett, who sings a chorus before engaging in some ad-libbed back and forth with AJ about sailing off to Margaritaville.  —J.H.

This lovely reflection on aging was originally recorded with a meditative reggae lilt and a horn section by Texas singer-songwriter Stephen Bruton in 1998. Buffett and Martina McBride refashioned it as a wonderfully empathetic country duet for Buffett’s 2004 collection License to Chill, where he also appeared alongside Kenny Chesney, Bill Withers, Nanci Griffith, Toby Keith, and others. Against sunrise guitars, the pair get adorably comfortable in the strange space between resignation and contentment, between embracing the past and hanging on for tomorrow as best you can. —J.D.

By this time, Buffett had become a North Star for mainstream country music, which was producing big hits by coopting his beachy sounds and imagery. He leaned hard into radio-country himself with this track written by Music Row heavyweights Mark Irwin, Josh Kear, and Chris Tompkins about a rowdy bar on the Alabama border. “At the Bama Breeze,” Buffett sings, you could shoot pool, act a fool, and play it cool. While more polished than some of Buffett’s best songs, it proved he could compete with the country stars he so influenced.  —J.H.

Buffett could have easily called this song “A Pirate Looks at 67.” A  burnished, late-period gem from Songs from St. Somewhere, it returns to the themes of his youth but from an older, been-there-sailed-that perspective. “It seems to me my life’s still free and wild,” he admits, but the melody, far less jaunty than in the past, suggests he knows he’s starting to wind down. With its haunted pedal steel, the song is more reminiscent of mid-Seventies Neil Young than Buffett’s own work from that time. — D.B