Of the many collaborations that Jazz Fest 2017 yielded, Jimmy Buffet coming out to croon with Dave Matthews was the most unexpected, but also one of the best surprises. While I’m not a full throttle Parrothead, I do enjoy some Buffet tunes, especially “A Pirate Looks at Forty.”

Dave and Tim are working there way through their spring and summer tour and made their way to NOLA to be one of the headliners at Jazz Fest. Despite being a headliner, their setlist was only 15 tunes—which is standard for a headliner spot. Towards the end of the set, Dave welcomed Jimmy Buffet to the stage.

Buffet shares some love and admiration for Dave before the songs starts and Dave returns the favor by cracking a joke about Jimmy’s shirt. This isn’t the first time that Dave has taken a crack at the classic Buffet tune. Dave and Tim covered “A Pirate Looks at Forty” way back in 2008 with Jack Johnson.

Although undoubtedly unrehearsed, the trio does a beautiful job and does the song justice.

Thanks to Chester Copperpot for the fantastic multi-cam production!