[3] The song contains the bittersweet confession of a modern-day, washed-up drug smuggler as he looks back on the first 40 years of his life, expresses lament that his preferred vocation of piracy on the high seas was long gone by the time he was born, and ponders his future.
Cash Box said the song has "an almost reggae progression, fine guitar playing and lead solo, [and] moving lyrics".
Dave Matthews alongside Jack Johnson performed the song at Kokua Benefit Concert at the Waikiki Shell in Honolulu in 2008.
Dave Matthews Band performed the song to open their show at The Gorge Amphitheatre the day after Buffett's death in 2023.
The music video was shot live on location at a resort in Mexico with thousands of fans surrounding the singers while performing.