* ColbertBump, RescuedFromTheScrappyHeap: If you look at his youtube videos you will find frequent mentions of going BACK TO THE GOOD PART, which apparently involve JohnnyDepp and [[{{Kraken}} Giant Squids]]. Basically, his LonelyIsland appearance was so freaking epic it earned him a ''lot'' of [[NewbieBoom new fans]]. It helps that PiratesOfTheCaribbean 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 VindicatedByHistory 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 TommyBoy references, OfficeSpace jokes and WTHCastingAgency reaction to Lady Gaga's support for him, Michael Bolton may finally have the last laugh over his critics.
* CrowningMusicOfAwesome: [[TwoWordsObviousTrope Three Words]] - "[[Disney/{{Hercules}} Go the Distance]]".
** One word less than that - "[[Music/TheLonelyIsland Jack Sparrow]]"
* GrowingTheBeard: ''The Hunger'', the album where he mostly stopped trying to be a [[Music/{{Foreigner}} Lou Gramm]] copycat.
* MemeticBadass: His appearance in Lonely Island's 'Jack Sparrow' is slowly granting him this privilege.
* OlderThanTheyThink: He recorded his first two albums in the mid-1970s under his birth name (Michael Bolotin) which have been largely forgotten.
----