Track 4 from Living And Dying In 3/4 Time (1974)

Tracks 5 and 6 from A1A (1974)

Tracks 13 and 14 from Volcano (1979)

I'm actually the son of a Parrothead, kind of. In the 2000s my late father had a few friends that loved Jimmy Buffett and he started going along with them to concerts, so in his later years I heard quite a bit of Buffett around his house, although I never went to one of the shows with them. When I went through Buffett's albums over the weekend after the news broke, I recognized more of his songs than I thought I knew. I've referred on here a few times to my gig as a teenager running sound for my friend who gigged around Delaware as an old-fashioned crooner, he mostly did Sinatra-type stuff, but "Margaritaville" was probably the most 'recent' song in his set, I was always expected to lead the "salt, salt, salt" chants. 

Buffett's debut Down To Earth was released on a tiny label and sold in small numbers (its follow-up, High Cumberland Jubilee, would remain unreleased for a few years until he had made a name for himself that the label could capitalize on). But "The Captain and the Kid" was the one song on that first album that sort of foreshadowed the sound and identity Buffett would soon establish, and he re-recorded it on a couple later albums. 

Buffett had a 'Big 8' set of signature songs that were played at every concert for many years, which consisted of 7 singles as well as "Why Don't We Get Drunk." That song appeared on the b-side of his first charting single, "The Great Filling Station Holdup," and the infamous "why don't we get drunk and screw" chorus made the song popular on jukeboxes even if the song was never quite suitable for radio play. "Making Music For Money" was written by Alex Harvey, and recorded in 1974 by both Jimmy Buffett and The First Edition (a few years later, First Edition frontman Kenny Rogers recorded the song on his biggest album, The Gambler). Both Buffett and Rogers sound convincing singing the song, even though they both went on to make a ton off money off of music. One of the cool surprises of Buffett's later albums is that he covered the great Crowded House song "Weather With You," the original of which was a hit all over the world but not released as a single in the U.S. 

A lot of artists who were commercially successful in the '70s just completely fell off the charts in the '80s, and Jimmy Buffett is a pretty extreme example. Buffett had several platinum gold albums in the '70s, and several more in the '90s, but none of the eight albums of original material he released in the '80s have been certified. The exception is his 1985 compilation Songs You Know By Heart, which collected songs he released in the '70s and became his best-selling release, going platinum seven times over. Most of that albums' certifications were in the '90s, when Buffett really became a one-man cottage industry, releasing books and opening restaurants and bars. The only non-singles on that release were "Why Don't We Get Drunk," "Boat Drinks," and "Son of a Son of a Sailor," which was the only song Buffett ever performed on "Saturday Night Live" (there were 2 musical guests that night). 

Buffett's final album was a deep cut-themed sequel of sorts, 2020's Songs You Don't Know By Heart, with acoustic renditions of lesser known songs from his catalog, which he'd perform on request on his web series during the COVID-19 lockdown. "Twelve Volt Man" on one of those low-selling '80s albums, One Particular Harbour. 

Bob Dylan has covered "A Pirate Looks At Forty," and in a 2009 interview, Dylan called Buffett one of his favorite songwriters, praising a couple songs from A White Sportscoat And A Pink Curstacean, the single "He Went To Paris" and the deep cut "Death Of An Unpopular Poet." For his part, Buffett does a very goofy Dylan impression for one line on "We Are The People Our Parents Warned Us About." 

It kind of surprised me to learn when I was younger that Buffett had started out as a country singer, and had lots of success on the country charts in the '70s, since I just thought of his big hits as soft rock. But his Alabama roots become more evident when you listen to his albums. And eventually mainstream country started to sound a lot like him, beginning with Kenny Chesney's Buffet-referencing 1998 hit "How Forever Feels" and especially after Buffett's appearance on Alan Jackson's "It's 5 O'Clock Somewhere," probably the biggest country hit of 2004. Now, the country charts have been full of songs about getting drunk on boats and beaches for a couple decades straight, although fairly few of them have the same wit and panache that a real Jimmy Buffett song has.