- Awesome Music: "Go the Distance".
- One word less than that - "Jack Sparrow"
- Colbert Bump, Rescued from the Scrappy Heap: 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.
Seth: Michael Bolton? Destroyed. [...] When Michael Bolton gets up, you donít think "Iím gonna get my balls blown off".
- 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.
- 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.
- 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.
- 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.