- 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 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 What the Hell, Casting Agency? reaction to Lady Gaga's support for him, Michael Bolton may finally have the last laugh over his critics.
- Crowning Music of Awesome: Three Words - "|Go the Distance".
- 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.
- Older Than They Think: He recorded two albums in the mid-1970s under his birth name (Michael Bolotin) which have been largely forgotten.