- Awesome Music:
- Dork Age: In the 80s, before he switched to his more successful adult contemporary sound, Michael Bolton was part of the hair metal scene. You read that correctly. Not exactly WASP or anything; think Winger, or Vixen. There's a bit of divide here, because some critics despise this era of his, but it's not uncommon to read comments from fans of hair metal who liked his rock music better. Either way, it's really strange to look back on this period.
- Hilarious in Hindsight: Michael Bolton's over-the-top balladry was a frequent target of 1990s comedians, and he even got frequent potshots from Ryan Stiles on Whose Line Is It Anyway? The late Bill Hicks, in particular, haaaaaaated Michael Bolton, even telling audiences "you know how phony he sounds, right??" Flash forward to 2017, where he has a new fandom in the comedy world and does a Netflix special with a plethora of comedians, some of which (Bob Saget, Janeane Garofalo) were Hicks' peers back in the day.
- Growing the Beard: The Hunger, the album where he mostly stopped trying to be a Lou Gramm copycat.
- Memetic Badass: His appearance in Lonely Island's 'Jack Sparrow' is slowly granting him this privilege.
- Narm Charm: He's this to the younger generation. Older fans of adult contemporary from way back, it's just, well, regular charm.
- Just the video for "Said I Loved You... But I Lied." Unbuttoned shirts, belting it out in the mountains, all that denim, the excessive fades to wildlife.
- Never Live It Down:
- When singing the national anthem at a Yankees game, he forgot the lyrics, so he read the lyrics he wrote down on his hand. When this happened, the man was nearly booed out of Yankee Stadium, but he was able to redeem himself by the end, because he's Michael Bolton.
- Also the "Love is a Wonderful Thing" plagiarism case. As explained in Suspiciously Similar Song, the conventional wisdom is now that the jury messed up.
- Older Than They Think: He recorded his first two albums in the mid-1970s under his birth name (Michael Bolotin) which have been largely forgotten.
- Rescued from the Scrappy Heap:
Seth: Michael Bolton? Destroyed. [...] When Michael Bolton gets up, you dont think "Im gonna get my balls blown off".
- If you look at his youtube videos you will find frequent mentions of going BACK TO THE GOOD PART, which apparently involve Johnny Depp and Giant Squids. Basically, his The Lonely Island appearance was so freaking epic it earned him a lot of new fans. It helps that Pirates of the Caribbean is already the object of much affection by the public, and that a fourth movie came out two weeks after the video premiered.
- What "Jack Sparrow" may have managed to do is a very strange form of Vindicated by History; Michael Bolton was a major YMMV singer at the height of his career. People either loved him (often soccer moms) or he was derided constantly (often stand-up comedians). Now, 20 years later, the Internet generation, which is tilting toward a demographic that wasn't even born during his most successful years, loves him. For all the Tommy Boy references, Office Space jokes and WTH, Casting Agency? reaction to Lady Gaga's support for him, Michael Bolton may finally have the last laugh over his critics.
- Apparently when he did an impromptu performance of "When A Man Loves A Woman" at a Saturday Night Live afterparty, both Jimmy Fallon and Seth Meyers commented that they were completely blown away by it.
- Signature Song: Either his original composition, "How Am I Supposed To Live Without You," or his cover of Percy Sledge's "When A Man Loves A Woman." Both songs were number-one hits and Grammy-winners. "Go The Distance" might be this if you're a Disney nerd.
- Suspiciously Similar Song: Subject of one of the most notorious copyright infringement lawsuits of all time, when The Isley Brothers sued him, alleging that his 1991 hit "Love is a Wonderful Thing" was a ripoff of their 1964 song of the same title. At first, with Bolton's professed love of Soul, this seemed like an open-and-shut case, but there were a couple of issues that seemed to tip the scales in favor of Bolton—the Isley song was really obscure, having only been released as an unsuccessful single in 1966, and never reissued after that. And the similarities boil down to both songs being uptempo Soul songs with the same title, with the title phrased similarly in the chorus (with different melodies), but otherwise not really sounding alike. Still, a jury ruled against Bolton and awarded the Isleys $5 million. Bolton appealed all the way to the Supreme Court, with the Recording Industry Association of America even filing an amicus brief on his behalf (arguing that the ruling was unfair because there's no clear legal standard for what counts as musical plagiarism), but they turned the case down. Many observers of the case, while expressing solidarity for the Isleys, felt that Bolton got a raw deal in the matter. Entertainment Weekly asked eight music critics their opinion, and while they almost all took potshots at Bolton, five of the eight said they didn't think he was guilty.
- Tastes Like Diabetes: Michael Bolton songs tend to go straight for "tender ballad" and milk it for all its worth. He's probably second only to Air Supply in that regard.
- Vindicated by History: It's a lot more accepted to admit you like Michael Bolton's music now, than it was at the end of the 90s. Doing comedy and being an affable, charming guy in interviews helped a lot with his reputation. It's also easy to approach his catalogue with fresher ears now, and wonder what all the hubbub was around a guy singing a bunch of old R&B hits that he clearly loves.
YMMV / Michael Bolton