- Critical Dissonance: His first Duets album was widely panned on release as a cynical, artistically negligible cash-in product. It then turned out to be the biggest-selling album of his career by a considerable margin.
- Cult Classic: The 1970 album Watertown, his one major attempt at contemporary pop/rock music. While it sounds like it might've just been another case of We're Still Relevant, Dammit!, he elected to do an ambitious Concept Album about a middle-aged small-town man whose wife has abandoned him and their two young sons. A flop when it was released, the album was rediscovered in later years, and the unusual subject matter, some striking musical arrangements, and Sinatra's understated, poignant vocals have earned it an enthusiastic following, even among people who aren't really fans of his music in general. There are many websites, articles and blog posts devoted to the album.
- Growing the Beard: In The '40s, 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 '40s 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, critical acclaim for his powerful performance as a heroin junkie in The Man With the Golden Arm and demonstrated several more times that it was no fluke.
- Frank Capra went so far as to say that if Frank gave up singing to concentrate on acting, he could have been one of the greatest actors of all time.
- Heartwarming Moments:
- "Me and My Shadow", sung with Sammy Davis Jr. is probably the best Heterosexual Life-Partners song.
- "My Way" doubles as both this and a Tear Jerker. 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.
- When Bela Lugosi died, he was virtually penniless. Sinatra quietly paid for the actor's funeral.
- When Lena Horne's white neighbors harassed her for living in an otherwise all-white neighborhood, he told her to call him if they gave her any more trouble. Nobody did.
- 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 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.
- Memetic Mutation: "Let me play Among Us."note
- 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.
- Tearjerker: His rendition of "Ol' Man River" is guaranteed to bring tears to any listener's eyes. Frank may be the only white singer who's ever done this song justice, fully conveying the pain that slaves went through in the Deep South.
- According to Frank Sinatra Jr, one person who was moved to tears by a performance of the song by his father was none other than Dr Martin Luther King himself, at a benefit concert for him at Carnegie Hall in 1961.
- We're Still Relevant, Dammit!: He released an album of folk covers and, of all things, a disco album in the '70s.
YMMV / Frank Sinatra