Sir James William Buffett, Esq. in an artist’s rendition of the oil painting on the cover of 1976’s Havana Daydreamin’. Hybrid math-art dad joke warning: A one-color drawing of a painting, isn’t that a bit derivative?

50 Years of Jimmy Buffett, in Eleven Songs

Famous now as the shallow and demispiritual leader of the Parrotheads, Jimmy Buffett also wrote some of the most beautiful and substantial songs of the late 20th century.

James William Buffett was born on the coast of the Gulf of Mexico in Pascagoula, Mississippi. He lived in various places, flirted with several colleges around the Gulf before getting a degree in history, and worked both as a yachtie and as a music journalist very early in his career.

These on-the-ground experiences give Buffett’s songs the heft and complexity of, well, real life. His early work couldn’t be more different from the pie-in-the-sky escapism and costumey casualness of 2018’s Hawaiian-shirt Buffett.

(2020 update: I’ve made a Spotify playlist that pairs with this primer, especially helpful since a few of the videos are gone.)

The Captain and the Kid (1970 original)