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1* ArchivePanic: He recorded an estimated 1,200 songs over a solo career that spanned nearly 50 years.
2* CriticalDissonance: 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.
3* CultClassic: The 1970 album ''Watertown'', his one major attempt at contemporary pop/rock music. He could've just done a simple cash-in, but instead he elected to do an ambitious ConceptAlbum 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.
4* CoveredUp: Most of what he recorded became ''his'' songs, such as "Fly Me to the Moon", "My Way", "The Lady is a Tramp", and "New York, New York" (for the last one, original artist Creator/LizaMinnelli complained that Yankee Stadium played Sinatra's version after the Yankees won, and hers if they lost; so they decided to play Frank's version exclusively, win or lose).
5* CreatorWorship: In the 1940s, Sinatra was just worshipped by women and hated by men. From the 1950s on he reinvented himself as a self-made man who is confident, but not afraid to show his inner emotions about feeling lonely. This won him his legions of new fans, even among men or people who didn't think popular music could have such depth. He became so identifiable that people just refer to him as "The Voice", as if no other great singing voices ever existed.
6* FanNickname:
7** Sinatra has long been referred to by fans and media as "Ol' Blue Eyes" on account of, well, his distinctively blue eyes.
8** "Chairman of the Board" became a popular nickname for Sinatra after he established Creator/RepriseRecords in search of greater creative freedom.
9* GermansLoveDavidHasselhoff: Frank Sinatra and the Rat Pack are still widely popular in Japan despite their fandom in English-speaking countries fading down to people who remember them as classic. Bookstores in Japan seem to contain more Rat Pack biographies than actual Japanese books and you can't walk by a karaoke bar without hearing "My Way".
10** In the Philippines, "My Way" has been so treasured that people have been ''killed'' for singing it incorrectly at karaoke bars. No joke.
11* GrowingTheBeard: In TheForties, Frank Sinatra began his career as a TeenIdol, singing SillyLoveSongs that appealed to young girls through the late 1940s and early 1950s. But then, in 1955, he recorded ''Music/InTheWeeSmallHours'', a ConceptAlbum consisting of plaintive ballads about [[DarkerAndEdgier loneliness and heartbreak]], which was both musically and lyrically much more mature than his previous output. It signaled to the world his ability to take on anything.
12* SugarWiki/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.
13** Creator/FrankCapra went so far as to say that if Sinatra gave up singing to concentrate on acting, he could have been one of the greatest actors of all time.
14* SugarWiki/HeartwarmingMoments:
15** "Me and My Shadow", sung with Creator/SammyDavisJr is probably the best HeterosexualLifePartners song.
16** "Music/MyWay" doubles as both this and a TearJerker. 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.
17** When Creator/BelaLugosi died, he was virtually penniless. Sinatra quietly paid for the actor's funeral.
18** 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.
19** Sinatra was playing a show in Wisconsin when news broke that Music/ElvisPresley died, and dedicated part of the performance to his memory, telling the audience "We lost a good friend today."
20* MemeticMutation:
21** "Let me play ''VideoGame/AmongUs''."[[labelnote:Explanation]]Some listeners noticed that in "Fly Me to the Moon," when Sinatra sings "Let me play among the stars," if you cut the audio off right at the first "s," it sounds like he's asking to play ''VideoGame/AmongUs'', a video game which created a lot of memes in 2020-2021.[[/labelnote]]
22** If Frank Sinatra was a good singer[[labelnote:Explanation]]An edit of Sinatra singing with [[https://www.youtube.com/watch?v=yD7UtPfSryU a rendition]] of Music/TheLivingTombstone's ''VideoGame/FiveNightsAtFreddys'' song in his style, using the popular "If X was a good Y" format. Became memetic due to how it sounds just like a real Sinatra song, plus [[Memes/FiveNightsAtFreddys how memetic the franchise is]].[[/labelnote]]
23* NewerThanTheyThink: "My Way" and "[[Film/NewYorkNewYork New York, New York]]", the two songs most associated with him, were released in 1969 and 1980, respectively, well after his peak of popularity (from the late 1940s to the early 1960s). The latter is especially notable, as it became iconic almost immediately.
24* {{Tearjerker}}: His rendition of [[https://youtu.be/tDHxsc18Hkw "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 DeepSouth. 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 Rev. Dr. UsefulNotes/MartinLutherKingJr himself, at a benefit concert for him at Carnegie Hall in 1961.

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