- Awesome Music: "Go the Distance".
- One word less than that - "Jack Sparrow"
- 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.
"I need more pictures of horses!!!"
- 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. The conventional wisdom these days is that he probably got screwed; other than being soul songs with the same title, the Bolton and Isley songs aren't similar at all apart from the Title Drop in the chorus being phrased similarly (but with different melodies). The Isley Brothers' song had also been long out-of-print at the time.
- 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 donít think "Iím 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 Vindicated by History in reverse; Michael Bolton was a major YMMV singer at the height of his career. People either loved him or he was derided constantly. 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.
- 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.