Watch Dave Matthews Cover Jimmy Buffett Classic At ‘Howard Stern Show’ Studios
See Dave go solo acoustic for “A Pirate Looks at 40.”
By Nate Todd Dec 13, 2023 • 11:07 am PST

The Howard Stern Show shared video of Dave Matthews covering Jimmy Buffett. Dave delivered a solo acoustic rendition of the Buffett classic “A Pirate Looks at Forty.”
“A Pirate Looks at Forty” appears on Jimmy Buffett’s 1974 album, A1A. Buffett sadly died on September 1, 2023.
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Buffett influenced so many songwriters across genres over the course of his storied career, one of them being Dave Matthews, who has a history with “A Pirate Looks at Forty.” Dave and Tim Reynolds joined Jack Johnson to perform the song in 2008 for the latter’s Kokua Benefit Concert.
When Buffett passed, DMB was in the midst of their summer tour-closing run at The Gorge. The group kicked off their concert there on September 2 with “A Pirate Looks at Forty.” “Every time I ran into Jimmy it was like seeing an old friend,” Matthews wrote at the time of Buffett’s passing.
Dave also brought the song to The Howard Stern Show. Watch below:
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