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1* ArchivePanic: He has many more songs than just "The Big 10," and trying to get through all of his albums is almost certainly going to take a while.
2* EveryoneIsJesusInPurgatory: "Cheeseburger in Paradise" was inspired by Buffett being forced to eat only canned food and peanut butter due to a boating mishap in the Caribbean. When he eventually made landfall, he ordered a cheeseburger, and was very grateful to have eaten it. There's a small subset of parrotheads who think the song has a much deeper meaning than it actually does. To their credit, the line "I'm just a cheeseburger in paradise" fits in rather well with Buffett's whole persona of taking it easy on the islands. But there's some really off-the-wall theories as to what the song is about. All of these theories are inaccurate; Buffett has said multiple times that the song is about cheeseburgers.
3* HarsherInHindsight: The island on which "Volcano" was written, Montserrat, really was geographically and economically decimated by a series of volcanic eruptions in the 90s.
4* MisaimedFandom: His signature song, "Margaritaville", is a melancholy song about a loser who's drinking his life away in a tourist town on a beach somewhere. A woman was involved with him a long time ago, but at the end of the song, he acknowledges "it's my own damned fault" that things have ended up this way for him. Fans took the song as a party anthem, and Jimmy rolled with it.
5* RefrainFromAssuming: "And Screw" is not part of the title of "Why Don't We Get Drunk".
6* SequelDisplacement: His "debut" album ''A White Sport Coat And a Pink Crustacean'' was actually his third album (though his second album sat on the shelf for five years before being released to cash in on his newfound popularity).
7* SignatureSong: "Margaritaville", "Cheeseburger in Paradise." Buffett even named several of his restaurants and merchandise outlets after them.
8* TearJerker:
9** "He Went To Paris" is an unusually somber song for Buffett, about a man who moves to Europe to find himself and marries and has a son while there, only to lose his family in a war, which also left him disabled.
10** "Nobody Speaks to the Captain No More" is the story of the eponymous Captain's long, downward spiral in life. It never gets better.
11---> ''So the story goes, he was dressed to kill, [[DrivenToSuicide when he jumped from the old mahogany mill...]]''
12** "Death of an Unpopular Poet" has the poet ultimately becoming famous and well-loved, [[DeadArtistsAreBetter but only posthumously]].
13** "The Captain and the Kid" is a slow, quiet tribute to his grandfather, a former merchant ship's captain. And according to [[WordOfGod Buffett himself]], its this song that kept him from ever signing with a major label. He was auditioning in Memphis, and played "The Captain and the Kid", and the record executive told Buffett that he loved the song, but it was too much of a downer. Apparently the executive said, "Why do you have to have him die at the end?" To which Buffett responded, "Because he did", and walked out of the record company's studio, never looking back once.
14** "Trip Around the Sun" (duet with Music/MartinaMcBride) is a somber song about growing older. While it does have a few uplifting moments about how "I'm gonna enjoy my trip around the sun," it carries the message that WeAllDieSomeday, which is a rather unusual topic for Buffett.

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