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How Michael Bolton Elevated the Past 20 Years of Comedy

In 1999, Bolton's career took a sharp turn — thanks to a movie he wasn't even in

Ever see a tweet that makes you nod so hard in agreement you pull a muscle in your neck? That’s what happened to me when I saw this 1 million percent correct post from comedian, Twitch streamer and internet star Rob Whisman:

First off, if you haven’t listened to the Lonely Island song he’s talking about, do yourself a favor and watch the sublime music video below. It’s even better now that Pirates of the Caribbean has lost whatever lingering cachet it had in 2011 — and it absolutely slaps.

This comedic subversion Whisman identified is the key to Michael Bolton’s entire (very successful) career. Entering the scene in the 1970s as a heavy-metal guy, he opened for Ozzy Osbourne with his band Blackjack, but then made the almost unthinkable transition to cheesy pop ballads. It all hinged on his breakthrough songwriting credit, “How Am I Supposed to Live Without You,” a version of which he recorded himself in 1988, becoming a world-renowned vocalist in the process. For the next decade, he was synonymous with adult contemporary/easy listening.

Then, in 1999, he had another star turn — without even showing up for the project.

Mike Judge’s Office Space.

The seminal workplace comedy Office Space featured a Michael Bolton of its own, this one plagued by the coincidence of having the identical name. He is forced to explain that he’s not related to the singer, takes a principled stand against going by Mike instead (“Why should I change? He’s the one who sucks”) and eventually sucks up to some corporate consultants by pretending to like Bolton’s music, only to find out they’re laying him off anyway. Where a lesser film would have dragged the real Michael Bolton in for a stilted cameo, Office Space was elevated by his absence: All you got was the punishing weight of his cultural presence, expressed by an increasingly angry white-collar geek.

And in a spicy twist, “Bolton” turns out to not even be the soft-rock star’s real surname.

Before his track with the Lonely Island, Bolton had a couple of amazing TV moments, too. In 2003, singing the National Anthem for the American League Champion Series at Boston’s Fenway Park, he committed the incredible faux pas of glancing at crib notes written on his hand after forgetting the lyric “were so gallantly streaming.” It happens at the 0:48 mark, and a chorus of booing rains down on him. If he’d executed this ideal provocation on purpose, it would put him on equal footing with the great performance artists of our time, but it’s just Bolton being Bolton, which is even weirder. Then, miraculously, he recovers, undercutting his own gaffe with a wild finale. Cheers erupt.

Or how about in 2010, when he and dancer Chelsie Hightower were the second couple eliminated from the 11th season of Dancing With the Stars, thanks to an awkward “Hound Dog” routine that opened with Bolton emerging from a… dog house? The YouTube comments are brutal enough, though one of the show’s judges, Bruno Tonioli, called their performance the worst jive of the whole series — a remark for which Bolton demanded an apology, noting that his 90-year-old mother had been in the audience. Even so, he had no regrets. “I’d do the dog house thing again in a second,” he said. “It was me having fun with myself.” And that, of course, has always been his strength.  

After “Jack Sparrow,” Bolton showed up for the climax of the Lonely Island’s movie Popstar: Never Stop Never Stopping, and, more recently, starred in the intentionally humorous Michael Bolton’s Big, Sexy Valentine’s Day special on Netflix, where he once and for all locked into the core of his appeal as a musical icon: He’s sincere, yet goofy, a guileless straight man who can satirize his own schmaltziness.

The A.V. Club noted that he made “a perfect foil” for the comedians featured in the variety show, a dude made funny in context — that context being his own improbable, faintly ridiculous role as a white interpreter of sultry black R&B classics like “Sexual Healing” and “(Sittin’ On) The Dock of the Bay.” Here, the telethon-like premise is that Bolton must sing to inspire the conception of thousands of babies to match a toy surplus at Santa Claus’ workshop — an idea the A.V. Club called “a hilarious assault on the very idea of conventional, heteronormative sexiness.” Along the way, he deconstructed plenty of other clichés.

What’s next for Bolton the comedian? Whatever the fuck he wants, I guess. That voice can do it all — even bring you around on the kind of corny hooks that made it famous.