• 02.09.17

Where We Sing The Praise of Michael Bolton, Comedy Icon

The multi-Grammy Award-winning singer/songwriter can do way more than belt “When a Man Loves a Woman,” and it’s about time he got his due.

Where We Sing The Praise of Michael Bolton, Comedy Icon
Michael Bolton’s Big Sexy Valentine’s Day Special

It’s the voice. A honeyed rasp that ages like rare cask single malt whiskey. Instantly recognizable in a crowded audio lineup. Triggering memories of long ago family car rides. Michael Bolton is the Prince of Pandora stations piped into office elevators everywhere. Lately, though, that velvety voice is more likely to make you laugh than swoon—and not ironically.


When Mike Judge’s working class lament, Office Space, came out in 1999, the film used Michael Bolton as a punchline. “Why should I change my name?” asks a character with the misfortune of sharing a name with the crooner. “He’s the one that sucks.” Fans of the film took it as read that this Michael Bolton, the lowly office drone played by David Herman, was right. The multi-Grammy Award-winning singer/songwriter behind “How Am I Supposed to Live Without You” was cornier than those corn-shaped cob tongs for eating corn. Cut to 18 years later, however, and it’s a different story. That Michael Bolton, the punchline, has undergone a radical transformation, becoming a punchline delivery system. And with the just-released Michael Bolton’s Big, Sexy Valentine’s Day Special on Netflix, he may have delivered his masterpiece.

It wasn’t as if Mike Judge was way off base with his assessment of Bolton in Office Space. The singer had emerged from his early ’90s heyday on the Adult Contemporary charts into a post-Nirvana industry that had little use for him. Attempts to navigate this brave new world included the shearing of his Samson-like signature locks, and cameos in things like The Nanny and Rodney Dangerfield’s Meet Wally Sparks. These appearances showed an interest in comedy–or the late-90s equivalent, anyway–but nobody professionally funny knew quite what to do with Bolton back then. Leave it to Andy Samberg and the Lonely Island crew to crack the code.

The obvious turning point, and the moment that has come to define Michael Bolton’s recent career reinvention, was 2011’s “Jack Sparrow.” The song and video debuted on a late-season episode of SNL, and instantly exploded into pop culture ubiquity. Samberg, Jorma Taccone, and Akiva Schaffer were prescient in picking up on how Michael Bolton was shockingly well preserved in both voice and chiseled appearance, and that he would be a hilarious musical foil. The idea proved more right than they could have possibly guessed.

The video starts with The Lonely Island in the studio, excited to work with their octaval hero. Bolton assures his admirers that after catching a Pirates of the Carribean marathon the previous night, he managed to write a big sexy hook for their new song. What follows is an abrupt juxtaposition, The Lonely Island’s would-be club banger intercut with Bolton’s gentle ode to “the jester of Tortuga,” Captain Jack Sparrow. It was a catchprase-generating turn that relied as much on the singer’s vocals as it did on his self-awareness as a dentist office icon, and his game willingness to go there. Unlike, say, Neil Patrick Harris’ cameo in Harold and Kumar Go to White Castle, Bolton wasn’t trying to obliterate his former image, but rather owning and playfully tweaking it. “Jack Sparrow” was a revelation that’s been seen over 160M times on YouTube, and it set the template for the next few years.

At that point, Bolton basically only had one joke—milking the cheesiness of his magnificent singing voice. He deployed this joke when Two and a Half Men came calling, and more successfully, when John Oliver needed a love song about the IRS on Last Week Tonight. He also reunited with The Lonely Island to sing the hook on the climactic song in their film, Popstar. In 2015, though, Bolton got the chance to broaden his comedic range. He starred in a video for Funny or Die that brought him full circle. “Office Space with Michael Bolton” allowed the singer to recreate David Herman’s homonymous role. He had gone from being the butt of the joke to being indisputably in on the joke.

With his new Netflix special, Bolton is now behind the joke as well. As executive producer, he helped put together the show, along with the combined talents of Comedy Bang! Bang!’s Scott Aukerman and Akiva Schaffer of The Lonely Island. Although Michael Bolton’s Big, Sexy Valentine’s Day Special relies on a writing staff partly cribbed from the now-departed CBB show, and a stacked lineup of cameos from the likes of Sarah Silverman and Andy Richter, Bolton himself has a lot of weight to carry here. He totally pulls it off.


The special takes the form of an improbable telethon in which lovers call to let Michael Bolton know they’re having sex on Valentine’s Day. Aside from singing his straightforward hits and a piano ballad version of “Jack Sparrow,” Bolton alternately plays the craggy-voiced straight man and goes as big and broad as the wackiness swirling around him. It’s a calling card for all he has to offer, and proof this new chapter in his career is no fluke.

Michael Bolton’s comedic range may be limited—he really can only play himself so far, or someone who shares that name—but there’s no limit yet to what he can do with what he’s got. Batten down the hatches for a wave of cameos, specials, and perhaps TV series that make Bolton so overexposed, we start to wonder, “How am I supposed to laugh without you?”

About the author

Joe Berkowitz is a writer and staff editor at Fast Company. His next book, Away with Words, is available June 13th from Harper Perennial.