Jimmy Buffett, who died on Friday at age 76, was the rare singer-songwriter who was keenly aware of the songs that comprised his core songbook.

Almost all of those tunes were written and recorded in the 1970s, the decade when he carefully assembled his signature beach bum persona by bringing country rock to the Florida Keys. He’d strike pay dirt with “Come Monday” and, especially, “Margaritaville,” songs that brought him into the pop mainstream and established the foundation of a career that brought him from the beach into Wall Street boardrooms. Buffett stayed on the road for decades, establishing new business ventures while also writing and recording fresh material. Still, he never lost sight of the handful of songs known as “The Big 8” that he had to play at every show.

“The Big 8,” which include such crowd-pleasers as “Cheeseburger in Paradise” and “Changes in Attitude, Changes in Latitude,” are at the core of Buffett’s catalog and they remain surprisingly resilient, retaining many of their roguish, silly charms after decades’ worth of repetition. As popular as they are, they don’t necessarily show the full range of Buffett’s skill as a songwriter. He excelled at character sketches and storytelling, developing an eye for geographical and generational details that made his best songs portraits of a particular time and place.

Here are 12 essential Buffett songs:

1. “He Went to Paris” (1973)

A character sketch inspired by a meeting with a Spanish Civil War veteran, “He Went to Paris” is an early example of Buffett marrying vivid imagery with economical storytelling. Buffett doesn’t hide a sentimental streak but he doesn’t overplay it either, landing upon a conclusion that extends far beyond this particular story: “Some of it’s magic, some of it’s tragic, but I had a good life all the way.”

2. “Death of an Unpopular Poet” (1973)

One of two songs Bob Dylan cited as proof of why Buffett was one of his favorite songwriters, “Death of an Unpopular Poet” contains some ties to “He Went to Paris.” Where the subject of “He Went to Paris” was a survivor, the poet here died before he could be celebrated. Buffett’s song chronicles the poet’s afterlife, once he had a verse published in “the Times,” leading everybody to scurry to find the genius, only to find that he left everything to his old hound. As bemused as it is bittersweet, it’s unmistakably Buffett in how it celebrates life lived on the margins.

3. “Grapefruit — Juicy Fruit” (1973)

“Grapefruit—Juicy Fruit” isn’t precisely a song about whiling away the hours on a beach but the mellow groove certainly feels like it was designed to soundtrack a peaceful afternoon. Buffett wrote “Grapefruit — Juicy Fruit” remembering the nights he’d take dates to a drive-in movie theater, a place where “you guzzle gin / Commit a little mortal sin.” The lightly jazzy swing keeps the song from wallowing in nostalgia; it’s less about the past as it is the amusement the memories generate.

4. “Peanut Butter Conspiracy” (1973)

    A galloping country and western saga, “Peanut Butter Conspiracy” finds Buffett turning stories of his early years as a troubadour struggling to keep himself fed into a riotous myth. The winding, witty storytelling and the distinct country bent underscore his debt to such early idols as Jerry Jeff Walker, an influence that would later be absorbed and never felt quite so clearly as it is here.
    5. “Pencil Thin Mustache” (1974)

    A laid-back number that flirts with Western swing, Buffett rhapsodizes about an outdated style of facial hair that conveys a certain classic Hollywood suavity. Buffett’s memories of Ricky Ricardo, Disneyland and “jazz musicians smokin’ marijuana” are delivered with lively, colorful wit.

    6. “Come Monday” (1974)

    His first pop hit, “Come Monday” is a gorgeous soft-rock single in which his pining for a distant lover feels comforting, not sad. Its warmth emanates from the loveliest Buffett melody ever composed — it sighs and sways with romantic grace.

    7. “A Pirate Looks at Forty” (1974)

    Written when Buffett was not yet 30, “A Pirate Looks at Forty” became something of a touchstone for the remainder of his career. The narrator isn’t quite precisely an outlaw: He’s a rogue who can feel his days of smuggling starting to fade, so he concentrates on fishing, drinking and chasing younger women. It’s a precise rendering of a specific kind of middle-aged melancholy that resonated with a singer and an audience that wound up growing old together.

    8. “Changes in Latitudes, Changes in Attitudes” (1977)

    The title itself conveys the notion that it’s possible to leave all your worries behind if you just head to another city far, far away. Buffett isn’t specifically rhapsodizing about beaches in the Florida Keys: he may wish he was sailin’ again, but he also wants to drink red wine in Paris, to go any of the places that have brought him pleasure.

    9. “Margaritaville” (1977)

    “Margaritaville” seems too unassuming to be a song to launch an empire; the vibe is blissfully mellow and the melody never pushes too hard, the lyrical details so carefully rendered they appear conjured, not written. The vaguely Caribbean breeze that blows through the song is so airy that it suggests a world without worry, whereas the song is actually about a drunk coming to the realization that his loneliness might be his own damn fault — a subtle detail but one that gives the song an emotional depth that chain restaurants and retirement communities named “Margaritaville” can’t quite wash away.

    10. “Son of a Son of Sailor” (1978)

    Like “A Pirate Looks at Forty” before it, “Son of a Son of a Sailor” benefits from a sense of middle-aged malaise. As he recounts the dreams he’s learned second-hand or through books, Buffett acknowledges that he wasn’t an active participant in adventures. There’s an acceptance of his fate at the heart of “Son of a Son of a Sailor” that gives it a bruised, understated beauty: He has wanderlust in his heart but he’s only searching for songs.

    11. “Cheeseburger in Paradise” (1978)

    “Cheeseburger in Paradise” bears a proudly ridiculous title but the song itself isn’t quite a novelty thanks to Buffett’s sharp punchlines about “that American creation on which I feed.” He sets that stage by recounting a couple of months where he was “losin’ weight without speed,” his healthy living making him yearn for a huge hunk of meat, realizing that very burger separates modern sailors from the guys who used to subsist on nothing but beer and bread. Those very funny verses sell a goofy bridge designed to get crowds to shout out loud at concerts, but even when he’s chanting about “Heinz 57 and french-fried potatoes,” it’s clear that Buffett was in on the joke.

    12. “It’s Five O’Clock Somewhere” (2003)

    Buffett didn’t write “It’s Five O’Clock Somewhere,” but it’s impossible to imagine it existing without him. Written by a couple of aspiring Nashville songwriters, the breezy drinking tune tapped into Buffett’s beach vibe, which is why Alan Jackson asked the singer to appear on his 2003 recording of the tune. The song became a phenomenon, ushering in a whole era of beachside country-pop, and Buffett eventually adopted it into his own sets.

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