Jimmy Buffett led one hell of a life and crossed paths with—and welcomed—all walks of life into his orbit. And so it was that in 2014, on Saint Barts, he took a liking to then SaturdayNight Live Weekend Update host to be Colin Jost.

“I was randomly seated next to him at a dinner, and I had never met him before, and I didn’t know it was him,” Jost recently told one Mr. Taylor Swift—err, footballer Travis Kelce—during the filming of the latter’s fledgling podcast, “New Heights.”

“I sort of noticed little, subtle hints that it might be Jimmy Buffett. Like, he would say something like, ‘Whenever I open a new Margaritaville…’” For what it’s worth, you have to give Jost the benefit of the doubt as, in his later years, Mr. Buffett had a sort of old-rich-white-dude mien that somewhat belied and even besmirched his storied, almost mythically rapscallion past and present wisdom.

And, lest we forget, Jost has earned his stripes in surfing and then some, per an exclusive sidebar during the 2024 Olympic Games in Tahiti with none other than SURFER editor Dashel Pierson.

“He was really gracious and knew I liked to surf,” Jost continued, “so he was like, ‘I’m gonna go surf tomorrow morning, why don’t you come and surf?’”

And who, pray tell, could say no to that? And before you get thinking that this was some practical joke that Buffett was staging upon an unsuspecting up-and-coming actor, know that he offered a little crash course in the spot in question (somewhere on the west coast of the island).

“He lent me a board, and we went out, and I remember when we were going out…Jimmy was like, ‘Be careful when you get into shallower water because there’s a lot of rocks. Don’t ride it all the way in,’” The sage Buffett told Jost, half a century or so his junior.

The understandably star-stricken Jost let those words in one auricle and out the other, and before he knew it, he was kicking out well inside of the area Buffett had instructed him to steer clear of. (It’s always the same story, “When the wave breaks here…”)

Only when Jost began to work his way back out to the peak, he noticed his forward paddle had no forward to it. His leash was wrapped. Ever vigilant, Buffett had eyes on his company (and likely his board from what was a very, very enviable quiver), and despite being waved off by an obviously embarrassed Jost, garnered the attention of a nearby “surf instructor” who, knife at the ready, swam out and saved the day with the loss of nothing more than a leash and a little pride.

Jost, who also recounted the tale in his 2020 memoir, A Very Punchable Face, was then directed to surf “down the beach,” by Buffett, who made no two ways about it.

Rest his soul, Jimmy Buffett had a knack for getting himself and those around him into trouble—that may be an understatement, if you listen to the legend and lore—but all the same, he was quick to save the day, too.

Related: Colin Jost Demoted from 2026 Olympics After Surfing Stint in Tahiti (Video)

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