* AcclaimedFlop: ''She Shot Me Down'' is widely considered one of the best albums from Sinatra's latter-day period, but significantly undersold compared to the commercial success of ''Trilogy: Past Present Future''. The album's failure would serve as the final nail in the coffin for the first incarnation of Creator/RepriseRecords (the label was already shut down in 1976 due to its declining commercial fortunes, but Sinatra, who founded the company, kept releasing his own material under its name for five years).
* BreakupBreakout: He first gained noticed in the vocal quartet The Hoboken Four, then as a featured vocalist for bandleaders Harry James and Tommy Dorsey before going solo in 1942 and becoming a huge star.
* ChannelHop: Being an immensely prolific artist who constantly fought for artistic freedom, Sinatra inevitably spread himself out across a number of labels. Initially signed to Creator/ColumbiaRecords, he moved over to Creator/CapitolRecords in 1954 before moving to his newly opened vanity label, Creator/RepriseRecords, in 1961. The Reprise deal would last even after its buyout by Creator/WarnerBrosRecords in 1963 and shuttering in 1976, with Sinatra keeping it alive for his own releases until the commercial failure of ''She Shot Me Down'' in 1981. In 1984, Sinatra would sign with Music/QuincyJones' own Warner-backed vanity imprint, Qwest Records, only to leave that label after the failure of ''L.A. Is My Lady'' and the scrapping of its planned follow-up in 1988. Sinatra ultimately returned to Capitol in time for the ''Duets'' duology in the early '90s.
* CreatorBacklash: He was not terribly keen on his SignatureSong "My Way" and showed contempt at having to always sing it. He had reservations about "New York, New York", although that was less dislike than fear of overkill. But most of all, he utterly despised "Strangers in the Night", which he called "a piece of shit" and "the worst fucking song" he ever heard. Nonetheless, he kept those songs on his set lists.
* HeAlsoDid: Sinatra was hired by ''Life'' to photograph the [[https://www.vice.com/en/article/ezedg7/frank-sinatra-once-photographed-muhammad-ali-and-joe-frazier March 8th, 1971 boxing match]] between UsefulNotes/MuhammadAli and Joe Frazier, the so-called "Fight of the Century"; one of his photos graced the cover of ''Life'''s March 19th edition. It's sometimes claimed that Sinatra was hired because he couldn't otherwise get a ringside ticket to the event, but in fact, Sinatra had a lifelong interest in photography and jumped at the opportunity to do it professionally. (That said, a lot of professional sports photographers were less-than-impressed with his work.)
* MultiDiscWork: ''Trilogy: Past, Present & Future'' was originally released across three [=LPs=] and three cassettes. CD reissues, meanwhile, squeeze the album onto just two discs, with disc one containing both ''The Past'' and ''The Present'' and disc two containing ''The Future''.
* SequelGap: ''Duets'' came out nine years after ''L.A. is My Lady'', owed to Sinatra's planned follow-up to the latter failing to materialize.
* WhatCouldHaveBeen:
** He was asked if he could perform the main theme for the ''Film/JamesBond'' film ''Film/YouOnlyLiveTwice'' and declined. His daughter Music/{{Nancy|Sinatra}} ended up with the gig.
** Sinatra intended to record a follow-up to ''L.A. Is My Lady'' in 1988, but this fell through for unknown reasons. Sinatra wouldn't record a true solo album again, with his next (and last) releases being the ''Duets'' duology in 1993 and 1994.
** When an adaptation of ''Nothing Lasts Forever'' was being made, he had a clause in his contract that he had the right to be offered to reprise the role of Joe Leland before they could offer it to someone else. He was 73 at the time, but the novel already had Joe being old and retired; it's likely it was written with the intent for him to be able to reprise the role without trouble. However, he turned it down, and eventually, the film became ''Film/DieHard'', the character was made younger, renamed John [=McClane=], and played by Creator/BruceWillis.
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