* CriticalDissonance: His first ''Duets'' album was widely panned on release as cynical, artistically negligible cash-in product. It then turned out to be the biggest-selling album of his career by a considerable margin.
* GrowingTheBeard: In TheForties, Frank Sinatra was a TeenIdol pop star with a fanbase of mostly teenage girls. That's right, during WorldWarTwo Frank Sinatra was Music/JustinBieber. But then, he TookALevelInBadass... (see the main page)
* HeReallyCanAct: An essential part of GrowingTheBeard above. In TheForties he co-starred in a couple of musicals with Creator/GeneKelly as a pleasant juvenile lead. Then he won that well-deserved Oscar in ''Film/FromHereToEternity'' and demonstrated [[TheManchurianCandidate several]] [[VonRyansExpress more]] times that it was no fluke.
* NewerThanTheyThink: "My Way" and "[[Film/NewYorkNewYork New York, New York]]", the two songs most associated with him, were not recorded until well after his peak of popularity (from the late 1940s to the early 1960s). The latter is especially notable, as it was only released in 1980, but became iconic almost immediately.