Jimmy Buffett’s 20 Best Songs: Critic’s Picks

Jimmy Buffett ably summed up his catalog with the title of his 1992 box set — Boats, Beaches, Bars & Ballads. But that cuts broader, and deeper, than many realize.

Buffett’s prevailing image, of course, was of floral shirts and Hawaiian leis, summer concert parties and fans with parrots on their shoulders and sharks, or at least fins, on their heads. And cheeseburgers on a paradise of tailgate grills. He also pioneered lifestyle branding, turning his tunes into an inclusive universe that includes restaurants, casinos, beer, real estate, radio and even a form of social media well before Mark Zuckerberg took the SAT. (Sadly, Buffett died at age 76 this week, as announced on his website, “surrounded by his family, friends, music and dogs.” His cause of death has not yet been confirmed.)  

Buffett’s signature lifestyle (and associated business ventures) sometimes eclipsed his music, and particularly to his songwriting. Before Margaritaville became a utopian state-of-mind, Buffett was an active and accomplished troubadour, writing songs in Nashville and busking in New Orleans before Jerry Jeff Walker introduced him to Key West and lit a conceptual light bulb Buffett would ride to fame and fortune. But he’s applied the same craft and literary flair from his folk club days to everything he’s recorded during the past 53 years — and the vast majority of his songs sound just as good sober as they do if you’re, well, wasting away in a grass skirt and coconut bra. 

So, we put down the margaritas for a moment to consider the 20 best Jimmy Buffett songs, from across his vast, 29-album catalog.

20. Jimmy Buffett, “Gypsies in the Palace”

The spoken-word introduction wears out its welcome quickly, but this lively country rocker about the mice playing — raising hell, actually — while the cat’s away is a welcome listen most any time.

19. Jimmy Buffett, “Livingston Saturday Night”

Buffett’s in fine country rockin’ form here, pumped up by a hot brass section and Greg “Fingers” Taylor’s fiery harmonica solo.

18. Jimmy Buffett, “Oldest Surfer On The Beach”

Mark Knopfler wrote this 2013 album track for Buffett, bringing something with poignant emotional weight to the Margaritaville man’s latter-day canon.

17. Jimmy Buffett, “The Great Filling Station Holdup”

Buffett’s contribution to country’s crime songs sub-genre is honky-tonk worthy 45 years later — and also has the distinction of being the A-side of “Why Don’t We Get Drunk,” which went on to even greater popularity.

16. Jimmy Buffett & Martina McBride, “Trip Around The Sun”

Country never seemed to trust Buffett enough (imagine that!) to make him one of the genre’s staples, but this 2004 duet with Martina McBride was worthy of its Top 20 status and doesn’t sound like it’s aged a minute.

15. Jimmy Buffett, “Pencil Thin Mustache”

At the ripe age of 28 Buffett was in a nostalgic and jaunty mood, name-checking Disneyland, “American Bandstand,” “Sky King,” Ricky Ricardo and more with genuine joy.

14. Jimmy Buffett, “Boat Drinks”

A 1979 B-side (to “Survive”) that’s nothing less than a Buffett mission statement, Caribbean flavored but driven by some meaty guitars that give these “Drinks” a bit more punch.

13. Jimmy Buffett, “It’s Midnight and I’m Not Famous Yet”

A rocking co-write with Steve Goodman from 1992’s Somewhere Over China. Buffett was already famous, to a degree, but it’s something of a foreshadowing to the Margaritaville mania that would build momentum in just a few years. 

12. Jimmy Buffett, “Volcano” 

Buffett plays historian, as it were, on this good-humored, Caribbean-flavored ditty about the real-life — and at the time dormant — Soufriere Hills volcano on Montserrat, where he recorded during May of 1979. For the record, Soufriere woke up again during August of 1995.

11. Jimmy Buffett, “Nobody From Nowhere” 

The existential opening track from 2009’s Buffett Hotel rides a cool, slightly country-flavored groove that slow burns into a gospel-tinged soul chorus. A gem that merits more attention and appreciation.

10. Jimmy Buffett, “Why Don’t We Get Drunk”

The songwriting debut by one Marvin Gardens (a Monopoly-inspired pseudonym for Buffett) is tongue-in-cheek country — not quite parody, but definitely acknowledging that he got the joke, too. 

9. Jimmy Buffett, “Changes In Latitudes, Changes In Attitudes” 

A pure Buffett travelogue that goes down as easy as a Mai Tai at sunset. Interesting fact: The “sons of b–ches” lyric has to be edited to “some bruises, some stiches” when the single came out during 1977.

8. Jimmy Buffett, “Come Monday”

The Buffett go-to ballad, cottony and gentle, was his first Hot 100 top 40 hit and top five on the old Easy Listening chart, a categorization it would take him a minute to climb away from. 

7. Jimmy Buffett, “One Particular Harbor” 

A buoyant, dynamic delight inspired by island travels, with an infectious chorus groove and recurring lyrics in Tahitian for authenticity. If the original 1983 production feels a bit tame, subsequent live arrangements gave the tune more lift-off.

6. Jimmy Buffett, “A Pirate Looks at Forty” 

Buffett was only 28 when he released this gentle rumination for, and about, a real-life drug-smuggler, but he ably conveys a blend of world-weary resignation and still-simmering desire.

5. Jimmy Buffett, “Margaritaville”

As much a state of mind as a song, Buffett’s cinematically drawn nirvana is still an absorbing listen, even if it’s been turned into maybe the best branding device pop music has ever witnessed.

4. Jimmy Buffett, “Cheeseburger In Paradise”

A buoyant and sincere celebration of high-calorie, high-cholesterol and high-spirited goodness that even a vegan could get behind, even if they don’t consume. That’s OK — we’ll take theirs.

3. Jimmy Buffett, “He Went to Paris”

Buffett has periodically celebrated this one, about a Spanish Civil War veteran he met while he was performing in Chicago, as one of his favorite compositions. Bob Dylan apparently likes it, too — and so should any Parrothead worth his or her Margarita salt. 

2. Jimmy Buffett, “Fins” 

Fun, and funny, this was Buffett’s best rocker even before the Parrotheads started making the en masse dorsals above their heads at concerts.

1. Jimmy Buffett, “Son of a Son of a Sailor”

The best Jimmy Buffett song isn’t one for hoisting boat drinks; It’s more fit for sippin’ at sunset, watching the other crafts sail in after you’ve tied yours in the slip.