* 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.
* CrowningMomentOfHeartWarming: "Me And My Shadow", sung with Creator/SammyDavisJr is probably the best HeterosexualLifePartners song.
** Doubles as a TearJerker is the song [[Music/MyWay "My Way"]]. As he contemplates his life Frank admits that while he's made plenty of mistakes he's still proud of it, claiming that he lived it his way and no one else's.
* 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'', critical acclaim for his powerful performance as a heroin junkie in ''The Man With the Golden Arm'' and demonstrated [[Film/TheManchurianCandidate several]] [[Film/VonRyansExpress more]] times that it was no fluke.
* MagnumOpusDissonance: [[Music/MyWay "My Way" ]]is Sinatra's most famous song, yet he didn't write it himself (Claude François' "Comme d' Habitude" was the originator) and he didn't like it that much himself. Many Sinatra fans would likely argue that there are better Sinatra songs around, yet nobody denies that it sums up pretty much everything that makes the singer great.
* 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.
* WereStillRelevantDammit: He released an album of folk covers and, of all things, a ''disco'' album in the '70s.