When Jimmy Buffett passed away on September 1st, 2023, the world didn't just lose one of the most iconic, transcendent, vibey musicians of his generation. The world also lost a pirate, a sailor, and a Parrothead. From the release of his debut album Down to Earth in 1970, Jimmy developed a fever, and the only cure was cranking out smash hit after smash hit—which made this list quite difficult to compose.
1. Margaritaville (1977)
True-blue Parrotheads might bang the table when they see “Margaritaville” rank as the top Jimmy Buffett song of all time, and I'll admit it's cliche. Don't blame me, though. Jimmy himself made the “Margaritaville” brand into a billion-dollar empire of hotels, casinos, bars, merchandise, and much more.
Plus, no Buffett song ever charted at number one aside from “Margaritaville,” so it is objectively the man's top hit.
2. Cheeseburger in Paradise (1978)
When Jimmy passed, fans dropped countless comments about how Buffett would now eat cheeseburgers in eternal paradise. He liked his with lettuce and tomat-a, Heinz 57 and French-fried potat-as.
Like Jimmy, we occasionally try to amend our carnivorous habits, but also can't make it more than 70 days.
3. Son of a Son of a Sailor (1978)
Few of Jimmy's songs capture his stress-releasing guitar play, modern-day piratehood, and knack for whipping up infectious choruses like “Son of a Son of a Sailor.” Rather than ramping up the crowd like “Cheeseburger in Paradise,” “Son of a Son of a Sailor” is the perfect song to fall asleep in a hammock to.
4. Come Monday (1974)
“Come Monday” was Jimmy Buffett's first Top-40 song, and it is as laid back as a Buffett anthem gets. Released in 1974 on the album Living and Dying in ¾ Time, “Come Monday” rings like a Laurel Canyon-era hippie love ballad.
5. Changes in Latitudes, Changes in Attitudes (1977)
You'll find that when Jimmy Buffett names an album after a song (or vice versa), the song is almost always a smash. “Changes in Latitudes, Changes in Attitudes” is no exception. While his 1977 also contained “Margaritaville,” no Buffett fan overlooks this ode to laughing in the face of life's stresses.
6. A Pirate Looks at 40 (1974)
Another classic with a slower pace than a sailboat on a windless day, “A Pirate Looks at 40” was a single off Buffett's 1974 album A1A. Despite what fans might assume, Jimmy is not referring to himself. In fact, he's referring to a smuggler who realizes that the fast life may have passed him by.
7. Volcano (1979)
Like “Fins,” “Volcano” deserves respect not because it is one of Jimmy's most vivid stories or technically impressive songs. Instead, “Volcano” has become an iconic Buffett anthem almost solely because of its catchiness.
Do you know a-where you're gonna go when the volcano blow?
8. He Went to Paris (1973)
The fourth single from Buffett's 1973 album A White Sport Coat and a Pink Crustacean, “He Went to Paris,” is exhibit A in Jimmy Buffett's uncanny ability to place listeners immediately and convincingly into some random person's shoes. We may not know who the heck Jimmy is talking about when he begins ruminating in song form, but by the end of the song, we feel like we've known the main character for years.
“He Went to Paris” was actually about musician Eddie Balchowsky, who served in the Spanish Civil War and met Buffett during a show in Chicago.
9. Treat Her Like a Lady (1979)
One of Jimmy's most soulful ballads, “Treat Her Like a Lady,” is a driving, heartfelt ode to the water. Live versions are especially memorable, as Jimmy's backup singers and band add layers and force to an already electric song. Double entendres were a Jimmy Buffett specialty, and “Treat Her Like a Lady” is one of his most memorable.
10. Havana Daydreamin' (1976)
This one is a personal favorite, as most Buffett fans have a song or two that speaks to them. “Havana Daydreamin'” conjures a sunny Cuban afternoon thanks to the requisite references to sugarcane, sailing, and daydreaming one's life away.
11. Mexico (1995)
Though not an original, you're lying if you say Jimmy Buffett's 1995 rendition of “Mexico” isn't the best version of “Mexico.” With all due respect to James Taylor, Buffett's upbeat, Southern-twanged, horn-boosted jam just feels like a sailing trip across the Gulf to the Yucatan peninsula, doesn't it?
12. It's Five O'Clock Somewhere (2003)
Though purist Parrotheads might lament the inclusion of such a commercialized song on this list, there's no denying the cultural impact of “It's Five O'Clock Somewhere,” which features Alan Jackson. If you're filling out your summer barbecue bingo card, hearing “Pour me something tall and strong, make it a Hurricane before I go insane” is a must-add.