Shortly before becoming co-anchor of Saturday Night Live’s Weekend Update in 2014, Colin Jost went on a New Year’s vacation to St. Barts with his then-girlfriend, Carmel Lobello. At dinner one night, Jost found himself seated next to “Margaritaville” singer Jimmy Buffett, but despite being a big fan of his work, Jost didn’t recognize him immediately. When Buffett mentioned something to Jost about his Margaritaville restaurant chain, the SNL star suddenly realized who he was talking to. The two got along well, and as Jost revealed in his 2020 book, A Very Punchable Face: A Memoir, Buffett invited him to go surfing with him the next day.
Although Jost considered himself to be a decent surfer at the time, Buffett still warned him to avoid going near the rocks by the shore of the secluded beach they were on. Jost then “immediately forgot” what Buffett told him and headed into the water with his surfboard. He started riding waves as high as four feet tall while Buffett hung back with his family. At one point, Jost hopped off his board next to the rocks Buffett told him about and noticed that he’d somehow gotten his leash caught underneath them.
Not wanting to look like a fool in front of Buffett, Jost tried to play things off when the singer asked him if he was OK. “Luckily, Jimmy Buffett can spot an idiot from fifty feet away,” Jost wrote in his memoir. Buffett paddled in to check on Jost and was horrified to find him pinned to the very rocks he’d instructed him to stay away from. “What are you doing?” Buffett asked. “I told you about the rocks!”
By then, Jost had a mouthful of seawater and could barely tread water. On top of that, he’d cut his foot on one of the rocks and was bleeding pretty badly. Thankfully for Jost, Buffett pulled out a knife that he apparently had gone swimming with and cut the leash off of his surfboard. After leading Jost back to safety, Buffett pointed him toward a gentler section of the beach and told him, “That might be more your speed over there.”
While recounting the story to Howard Stern and his Weekend Update co-host, Michael Che, a few years later, Che jokingly asked Jost, “Do you think surfing might not be for you?” “Maybe the water’s not your friend,” the comedian went on to suggest:
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