Photo: Allen Berezovsky (Getty Images)

In the early 2010s, Michael Bolton seemed as unlikely a candidate as any for a career resurgence. It’d had been over two decades since his ballads originally topped the charts and, in the interim, he had more or less emerged in the modern era as a dad-pop punchline. But, as noted in a new piece from MEL, Bolton added a new dimension to his career by turning being the butt of the joke in his favor.

Twelve years after being dubbed “the one who sucks” in Mike Judge’s Office Space, Bolton appeared on the Lonely Island’s hilarious “Jack Sparrow.” In the Pirates Of The Caribbean-themed club banger, Bolton amiably poked fun at himself while, most shockingly, committing wholeheartedly to what is one of stupidest bits imaginable. With the song, Bolton crossed what many might’ve assumed was an unbridgeable gap between the people who genuinely enjoy his music and the kids who dig absurdist millennial comedy. That’s no small feat. 

MEL describes Bolton’s revamped persona as “sincere, yet goofy, a guileless straight man who can satirize his own schmaltziness.” Post-“Sparrow,” his comedic stylings were put to use on John Oliver’s Last Week Tonight, where he sang a love song to the IRS; the Lonely Island’s Popstar: Never Stop Never Stopping; and on his very own Netflix special, Michael Bolton’s Big, Sexy Valentine’s Day Special, which was co-directed by Scott Aukerman and Akiva Schaffer.

Now, Bolton enjoys the kind of demographic-defying career that most artists would kill for, one he could pivot into a number of weird, exciting directions. Wherever he goes, though, we’ll always remember him as the softball-throwing killer that haunted Conan O’Brien.

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