When the World Decided Michael Bolton Was Funny and Cool

Writer Bill Zehme profiled easy-listening icon Barry Manilow for Rolling Stone in 1990, and he opened his piece with a devastating observation: “When your name is a punchline, you live in hell. Barry Manilow lives in hell.” Manilow’s fans disagreed, of course, but for the rest of us, Zehme tapped into something deeply true about our feelings regarding the adult-contemporary artist. His songs were so epically cringey that his very name came to embody something noxious. His name became a shorthand for cheesy.

Over the years, other artists have had to deal with a similar fate. Sure, they’re wildly popular, but to a contingent of music junkies, their bland, feel-good songs are anathema. For quite a while, one such artist was Michael Bolton. And in 1999, Mike Judge decided to literally make Bolton’s name a punchline in Office Space by giving one of his miserable office-drone characters (played by David Herman) the same name. It remains one of the funniest running bits in that comedy: No, he’s not related to the singer, damn it.

Live long enough and you’ll see pop-culture punching bags get reappraised and embraced. Kenny G? He used to be a joke — now, he’s almost sorta hip. Same with Celine Dion, whose critical drubbing had started to subside even before her recent diagnosis of stiff person syndrome. What was once terribly uncool is now forgiven — especially if the punching bag develops a sense of humor about himself. Which is why Michael Bolton has been the most successful of these artists in terms of changing his public persona. There was a time when the world thought he was unspeakably unfashionable. Then he learned to take a joke.

When music historians talk about the 1990s, they often cite the rise of grunge, indie-rock and hip-hop. “Alternative” became an industry buzzword. But not everything on the radio was nearly that edgy — lots of folks just enjoyed listening to mellow tunes. Artists such as Mariah Carey were huge in the ‘90s, and among the titans of adult-contemporary was Michael Bolton. He’d actually found success later in life — he’d been putting out records since the mid-1970s (and writing songs for other artists, including KISS and Cher) before finally making serious inroads on the singles chart himself in the late 1980s. And once listeners got a taste of his impassioned love songs, they couldn’t get enough. Hits like “How Am I Supposed to Live Without You,” “How Can We Be Lovers?,” “Love Is a Wonderful Thing” and “Time, Love and Tenderness” made romance their central subject — and don’t forget his strenuous covers of R&B chestnuts like “(Sittin’ On) The Dock of the Bay” and “When a Man Loves a Woman.” In the ‘90s, he probably inspired a lot of long-distance dedications and wedding first dances.

With his big pipes and sensitive-hunk-next-door vibe, Bolton was a nonthreatening sex symbol whose glistening pop ballads went down smooth. (His stuff is tailor-made for a dentist’s office.) He was corny and earnest, his persona as square as his oversung declarations of romantic bliss or emotional devastation. There was nothing subtle or cool about him or his music, which made it very appealing to people who weren’t that concerned about being hip. “I do recognize that my music has carried a certain perception of who I am and I definitely consider myself a hopeless romantic,” Bolton said in 2020, and his unapologetic sappiness made him a laughingstock among those who rolled their eyes at his syrupy sentimentality. 

But by the end of the 1990s, Bolton’s popularity had started to dip. He even made the decision to let go of the mullet, which had been part of his look (and part of the reason why so many of us couldn’t take him seriously). “I cut my hair at the height of my success,” he would say later. “I didn’t feel like long hair was what was driving the success I was having. But it’s funny how in hindsight the look can be so heavily ingrained. I was in London doing promotion for a tour, and on the world news was, ‘Michael Bolton Cuts Hair.’ … It was so funny and surreal.”

With Bolton’s stardom slipping, he was the perfect target for Judge as he was working on the script for Office Space, which was about some guys at a soul-crushing office job who decide to strike back at their bosses. Judge thought back to one such job he’d had when he was younger, and inspiration hit. “I just remember being in some office, and somebody just had soft rock playing all the time,” Judge said in 2019. “Michael Bolton was playing all the time. I’m bad at naming characters. I like giving them normal names. I didn’t want him to have a cool name, and then I just thought, ‘What if I make it a famous person, somebody he hates?’” 

And, just like that, David Herman’s character was Michael Bolton, who’d had a fairly normal existence through childhood until the other Michael Bolton got famous, permanently destroying our Michael Bolton’s life. Having the same name as any celebrity would be difficult, but for it to be someone who isn’t respected and often openly mocked, well, that’s hell. Herman’s Bolton made it clear just how much he loathed the famous Bolton, calling him a “no-talent ass clown.” 

“My original line about Michael Bolton was, ‘He’s a no-singing asshole,’ and we changed it to ‘no-talent ass clown,’” Herman told The Hollywood Reporter earlier this year. “There was something legal about, if you say he’s no-singing, the connotation is that he’s Milli Vanilli and not actually singing. ‘Ass clown’ really entered the vernacular because of the movie.” In fact, you can now look it up in Merriam-Webster, which has a very amusing entry on the phrase. All of a sudden, the famous Bolton didn’t just have a punchline name — Office Space made a specific insult about him dictionary-worthy.

Famously, Office Space bombed at the box office but became a cult hit, now arguably viewed as one of the 1990s’ best comedies. But even at the time, Bolton the singer was aware of it — and not happy. In a 2002 Entertainment Weekly interview, Bolton talked about being associated with the film. “Everything I do will be promotion for Office Space for the rest of my life,” he said. “They had to make that fucking movie! Do you know what it’s like having 22-year-old kids walk up to you and go, ‘Oh, my god, it’s, like, the real Michael Bolton. Like, dude, have you seen Office Space?’ I was doing fine. Then they made this movie, and I can’t go anywhere.” 

In subsequent years, that quote has been used to suggest that Bolton hated the movie or hated the joke, although it’s possible he was being a little tongue-in-cheek with his annoyance. (The rest of the interview is a very snarky back-and-forth between him and the writer.) Regardless, Office Space’s joke seemed to express something in the zeitgeist: Easy-listening dreck was just the worst, and Bolton was its poster child. Herman’s Bolton loved hardcore hip-hop, so of course he would hate the famous Bolton — and would be deeply offended that corporate lackey Bob Slydell (John C. McGinley) was actually a huge fan of his music. Culturally, Michael Bolton was a line in the sand — you either knew he sucked or were a hopeless normie. There was no middle ground.

In the early 21st century, Bolton kept putting out albums, although they rarely made a dent on the charts. His cultural relevance dried up, despite having younger fans who were working their way up the industry ladder. (A pre-fame Lady Gaga reached out to Bolton to collaborate on his 2009 album One World One Love, co-writing and providing backup vocals on “Murder My Heart.” “I love Michael Bolton, and I always have,” she told a reporter. “It was an exciting opportunity to work with someone as timeless as Michael and do a ballad.”) But the real career turnaround happened when he decided to lighten up.

Bolton’s appearance in the Lonely Island’s Digital Short “Jack Sparrow” was hardly the first time a cultural punching bag sent up his own image in a comedy. In 2004, Neil Patrick Harris did a career reboot by playing an asshole version of himself in Harold & Kumar Go to White Castle. It’s now a fairly familiar strategy in which the disgraced/mocked celebrity gets a second life by leaning into the thing you know about them. (I won’t spoil anything, but several of Deadpool & Wolverine’s cameos are built around this comedic premise.) Bolton liked the Lonely Island and their previous high-profile collaborations, but he still wasn’t sure when they reached out to work on a track together.

“I soon found myself in a conference room at a hotel in Los Angeles — my manager and me on one side of the table, and Akiva (Schaffer), Jorma (Taccone) and Andy (Samberg) sitting across from us,” he recalled to Vulture last year. “I said, ‘My daughters are so excited about me having this meeting with you guys.’ And they said, ‘Our moms are so excited about us having this meeting with you.’”

The Lonely Island pitched him the concept — Bolton and the trio are supposed to be writing a banger, but he keeps hijacking the track to sing about how much he loves the Pirates of the Caribbean movies — but the sticking point was just how vulgar Bolton was going to allow his vocals to be. “Even though I understood what was funny about it, I thought I could be insulting the first 10 rows of my live audience if I said ‘yes,’” he told Vulture. “I was playing at the Vatican, you know what I mean?” After a few back-and-forth rounds of revisions, though, Bolton was satisfied. Hell, he even agreed to sing “This whole town’s a pussy / Just waiting to get fucked” because it was a line from Scarface — although he insisted he had to be dressed like the Al Pacino character so it was clear he was paying homage to the film.

On May 7, 2011, “Jack Sparrow” premiered on Saturday Night Live. Bolton was at the show, nervous that it wouldn’t go over well. Instead, it became an instant sensation. As Bolton said in his Vulture interview, “I remember John Mayer was at the Saturday Night Live after-party the night it aired, and he said to me, ‘Tomorrow you’re going to see something you’ve never seen before. People are going to love this, and they’re not going to be expecting it from you, so it may even be bigger.’”

Indeed, “Jack Sparrow” was an unexpected left turn from an established star whose persona seemed set in stone. What was super-earnest Michael Bolton doing in a Lonely Island video? The trick to the clip was that Bolton was always the straight guy, oblivious to the fact that his manic devotion to Pirates of the Caribbean (and Erin Brockovich and Scarface) was torpedoing the song. He didn’t go for laughs, which just made it funnier. And because he always earnestly, emphatically belted out his love ballads, a vocal tic that had become a gimmick at that point in his career, all he had to do was sing as he normally did for “Jack Sparrow” to be hilarious. It wasn’t just that the conceit of the song was funny — it was that it was that voice doing it.

Soon after, Bolton made a hard pivot toward comedy. He’d appeared on sitcoms before as himself, but he practically became a recurring character on Two and a Half Men, with the joke being that women cannot get enough of his sexy songs. He was suddenly vocal in interviews about loving Office Space and the Michael Bolton joke. “I told (Judge) I’m a huge fan of his and have autographed countless (Office Space) DVDs at my concerts over the years,” Bolton said in 2015. “The irony is that the movie’s character is the most pathetic of them all, so the fact that he’s not a fan of mine is actually a compliment. What I’d really like to do is make a sequel with the real Michael Bolton giving the character some life advice, ‘cause life isn’t doing so well for him, and the poor guy’s clearly in need of some direction.” That sequel has yet to see the light of day, but Bolton did shoot a Funny or Die video in which we see him “audition” for the original film.

In our modern society, we’ve generally become more tolerant of artists who, not that long ago, seemed uncool. Blame it on poptimism or the fact that there are bigger problems in the world than whether or not Ed Sheeran, in fact, sucks, but Bolton’s redemption tour was well-positioned. There are enough actively horrible men in the world — why hate on a guy whose biggest crime is his treacly, laughably sincere music? Bolton rode that goodwill to appear on everything from Fresh Off the Boat to Clone High to Awkwafina Is Nora From Queens, the idea always being, “Hey, look, Michael Bolton’s not so bad.” 

Bolton kept showing up in more Lonely Island projects, too. He sang with them on “Incredible Thoughts” in Popstar: Never Stop Never Stopping and had his own Netflix special, which was overseen by the group (as well as Comedy Bang! Bang!), called Michael Bolton’s Big, Sexy Valentine’s Day Special. Reviewing Big, Sexy for the A.V. Club, Esther Zuckerman hit upon an indisputable fact: “He is not a good actor by any means, and he probably wouldn’t be funny out of context. His delivery is bland, and his conventionally handsome, Ken-doll face doesn’t register much emotion.” As she points out, his blankness worked well opposite his actually funny costars, but considering the special derived its name from Bolton’s line in “Jack Sparrow” about giving the guys a “big, sexy hook,” it was clear he was milking his Digital Short rebirth for all it was worth. 

After years being away from the center of the musical ecosystem, Bolton figured out how to get back there thanks to comedy. Last fall, he noted, after the Digital Short premiered, “younger people in the streets would recognize me — it would be about ‘Jack Sparrow’ and about the comedy, when for many, many years before, it was always about long hair, the hits. … The people who love this video were eager to hear what I was doing next musically.” Now more willing to laugh at himself, he’s discovered something previous punchlines like William Shatner learned: If you prove you’re in on the joke, it takes the sting out of it. Plus, it makes you seem cool and self-aware. Crazy to think this probably all started because Bolton got dissed in Office Space. David Herman, the man who played the non-famous Bolton, definitely was aware of the irony.

“I think at the time Michael Bolton was a perfect target,” Herman said in 2019. “He had taken himself so seriously and was such a perfect guy to ruin our Michael Bolton’s life. Today he doesn’t take himself quite as seriously, which takes some of the piss out of it.”

Bolton is back playing himself this weekend. He shows up briefly in The Fabulous Four, a mediocre comedy starring Susan Sarandon, Bette Midler, Megan Mullally and Sheryl Lee Ralph as reunited best friends. Bolton performs at a reception — naturally, these women all think he’s dreamy — but he isn’t given time to do any comedy. He’s just being Michael Bolton, that mega-platinum figure of derision who, gradually, people decided was cool. Well, maybe not cool, but tolerable at least. 

One thing’s for sure, though: His hair looks a lot better.