Five Jimmy Buffett Ballads you Shouldn’t Ignore

Like so many Florida kids, I came of age to a steady calypso-influenced soundtrack of “Boat Drinks” and “Changes In Latitudes, Changes In Attitudes.” I was heartbroken to wake up on Saturday morning to the news that, after having battled skin cancer for the past four years, Jimmy Buffett has died. He was 76.

Growing up here in Jacksonville, I spent most weekends on my parents’ pontoon boat, fishing for reds near the mouth of the St. Johns River. Buffett’s four-disc box set, Boats, Beaches, Bars & Ballads, was the only music I have any memory of hearing out on the water. In an age where every millennial is hunting for ways to access their “inner child,” Jimmy Buffett’s tunes are a quick way to transport me back to sunburnt days near Fort George Island, wiping Publix fried chicken grease on my towel before jumping back into the brackish river. At age eight, I even named my pet fish Mr. Utley after a member of Buffett’s Coral Reefers Band—at one point during the song Volcano, Buffett cries out “Mr. Utley!” in reference to longtime band director Michael Utley.

While Buffett was best known for songs about island escapism with hits like Margaritaville and Fins, it was his ballads that came to mean the most to me. I’ve rounded up five Buffett ballads that we should definitely be paying attention to as part of his legacy. 

“A Pirate Looks at Forty“

A1A, 1974

“Mother, mother ocean, after all the years I’ve found

My occupational hazard being my occupation’s just not around”

While this song was written in 1974, its lyrics manage to feel more and more relevant to me as time marches on. Were I to hear these lines today for the first time, it might feel like Buffett was referring to industry obsolescence among Hollywood writers. Instead, he’s singing about the longtime dream of being a pirate. Every Buffett ballad is packed with wisdom and longing, but one element he never neglects is character development.

“Come Monday“

You Had to Be There, 1978

This one is, hands-down, Buffett’s most romantic song. Those sweeping strings! That tender pedal steel solo! It’s a musical replication of the feeling of falling in love. Plus, it contains one of the loveliest lines in music: 

“We can go hiking on Tuesday

With you, I’d walk anywhere” 

“Grapefruit – Juicy Fruit“

A White Sport Coat and a Pink Crustacean, 1973

Buffett was a lyrical master of lightening the mood in order to will his listener into darker territory. Beginning with tropics-centric references—grapefruit, a bathing suit, Juicy Fruit gum—the song moves into references of committing “moral sin,” feeling “so damn lonely.” But the lightness returns during a musical break, when Buffett calls out, “Ladies’ choice! Everybody dance.” Lyrically and sonically, he holds the good and the bad parts of life together in the same hand.

“Son of a Son of a Sailor“

Son of a Son of a Sailor, 1978

Another excellent example of developed character in Buffett’s lyrics, this modern-day shanty is coated with sentimentality, though not the cheap, sticky kind—he wrote the song as a tribute to his grandfather. A stray ship’s bell breaks occasionally through a whirring organ, tangled 12-strings, and a heartfelt chorus of backing harmonies.

“Hear the bells ring as the tight rigging sings

It’s a son of a gun of a chorus”

“Pacing the Cage“

Beach House on the Moon, 1999

Buffett at his most earnest, which is the artist I’ll be remembering. This song taught me that this musician is capable of so much more than “Cheeseburger in Paradise.” Originally written by Bruce Cockburn, the lyrics begin:

“Sunset is an angel weeping, holding out a bloody sword

No matter how I squint I cannot make out what it’s pointing toward”

I can’t even type out those lyrics without getting full-body chills, and I imagine Buffett felt the same way when he sang them. After all, a cover song isn’t necessarily about the cover itself—it’s about the decision to meditate on a certain song thoroughly enough to perform it. And that’s what comes through to me about Buffett’s creative process. He wasn’t swilling margaritas and joining the conga line the way so many of us have always imagined him. For the most part, he was out on the water, thinking and feeling and longing for something greater, or at least some greater understanding. He was pacing his cage.