YMMV: Frank Sinatra
- Critical Dissonance: 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.
- Crowning Moment Of Heart Warming: "Me And My Shadow", sung with Sammy Davis Jr is probably the best Heterosexual Life-Partners song.
- Growing the Beard: In The Forties, Frank Sinatra was a Teen Idol pop star with a fanbase of mostly teenage girls. That's right, during World War II Frank Sinatra was Justin Bieber. But then, he Took a Level in Badass... (see the main page)
- He Really Can Act: An essential part of Growing the Beard above. In The Forties he co-starred in a couple of musicals with Gene Kelly as a pleasant juvenile lead. Then he won that well-deserved Oscar in From Here to Eternity and demonstrated several more times that it was no fluke.
- Magnum Opus: In The Wee Small Hours is widely regarded as his masterpiece, though Songs For Young Lovers and Songs For Swingin Lovers are equally popular.
- Magnum Opus Dissonance: "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 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.
- Newer Than They Think: "My Way" and "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.