"A Pirate Looks at Forty" is a song written and performed by American popular music singer-songwriter Jimmy Buffett. It was first released on his 1974 album A1A and "Presents to Send You" is the B-side of the single.

Buffett wrote the song about Phillip Clark, at the Chart Room where Buffett first performed after his move to Key West, Florida. 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.

For radio play, the song was shortened by deleting the fourth verse for the single release. The song is one of Buffett's more popular, and is part of "The Big 8" that he has played at almost all of his concerts, and always during the second set.

Ian McNabb included a cover on his CD single "I'm Game" in 1993 which was taken from his solo album "Truth and Beauty".

Jack Johnson has been known to cover this song in many of his smaller concerts. It was officially released on the soundtrack to The September Sessions in 2002.

Roger Creager, a prominent Texas Country performer, covers this song as well and is featured on his live album Live Across Texas.

Bob Dylan and Joan Baez performed the song during their 1982 reunion performance at the Peace Sunday rally in Pasadena, California.

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