In the history of cinema, few celebrities have ever been mocked so brutally over the course of a movie as poor Michael Bolton in Office Space. We find out that one of the low-level employees the movie focuses on shares a name with him, and ever since he became famous in the late ‘80s, his life has been miserable. He also refuses to change his name, with the rationale of “Why should I change? He’s the one who sucks.†At no point do we see a cameo from the real Bolton, letting us know he’s in on the whole thing; rather, we’re left with the stark notion that Mike Judge and company must really hate this guy.
But if Michael Bolton was the butt of jokes in 1999, these days, he’s thoroughly in on the joke. It started in 2011, when he collaborated with The Lonely Island on the song “Jack Sparrow,†in which he reveals himself to be a huge film buff, while also singing several classic movie lines, including “This whole town is a pussy just waiting to get fucked!†from Scarface. It showed us an entirely new side of Bolton, far different from the adult contemporary star was omnipresent in the early ‘90s. His bit with The Lonely Island was likely the impetus for Michael Bolton’s Big Sexy Valentine’s Day Special, which was released on Netflix last month. Directed by Scott Aukerman and The Lonely Island’s Akiva Schaffer, the special features dozens of celebrity cameos and  centers around the premise that because Santa’s elves made too many Christmas toys, the world needs to conceive 75,000 new children, using the aid of, you guessed it, the music of Michael Bolton. It’s an absurd, off-the-wall premise, and proof that after “Jack Sparrow,†Bolton was more than down for another round of self-deprecation.
So, what caused this role-reversal? Why is Bolton not only so in on the joke, but more importantly, why does it work so well? Why is it that someone who never cared for Bolton’s music at all could look at what he’s done recently and think to themselves “You know, he’s actually a pretty cool guy!†Perhaps it’s because it never feels like Bolton’s trying to apologize for or convince us of anything. It never feels he wants us to change our minds and realize that “Can I Touch You…There?†is a secret masterpiece. He just wants to make us laugh, whether we enjoy his music or not. Compare this to a Funny Or Die video Nickelback made in 2011. After fans were upset that they’d been booked to play halftime at a Thanksgiving football game, they attempted to repair their image by appearing in a video in which let the world know “Hey guys, we know what you think of us.†The problem was, there wasn’t much of a joke beyond that. Were we supposed to think their music was good because they acknowledged that a lot of people think it sucks? The whole thing was confusing and directionless.
There are two key components to being able to make fun of yourself: humility and security. You have to understand that not everyone likes you and be more or less okay with that, while also understanding that a lot of people do like you. Bolton masters both of these tests. He understands that to many, his music is over-produced schlock, but many others like it, and the goal of “Jack Sparrow†and his Netflix special seems to be to give a laugh to people in both groups. If you’re looking for the opposite of Michael Bolton, at least in this regard, look no further than the Oval Office. Donald Trump has no sense of humility, nor does he appear to be secure in the knowledge that he won 306 electoral votes. That’s why he’s always yammering about “haters†and “losers.†He can’t accept that people don’t like him, and that’s why (or at least it’s one of the reasons why) his SNL hosting job was so cringeworthy. The dude has no idea how to make fun of himself, because in his mind, there’s no fun to be made.
Being able to make fun of yourself is an underrated characteristic. The ability to be self-deprecating means that you’re aware of your flaws, or at least what some people perceive your flaws to be, and you’re willing to accept these flaws, and make fun of them with everyone else. It’s a very humanizing thing, and in the case of Michael Bolton, it probably turned a lot of people who would never even consider buying on of his albums into lifelong fans. It seems like a weird thing to say, but if President Trump wants us to change our view of him, he could do worse than taking a cue from the guy who sang “How Am I Supposed To Live Without You?â€