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1[[quoteright:340:https://static.tvtropes.org/pmwiki/pub/images/img_0875.JPG]]
2[[caption-width-right:340:"Ring-a-ding-ding, baby."]]
3
4->''"He lives by an ancient code -- he's unforgiving of his enemies, protective of his friends."''
5-->-- '''Creator/AlanKing''', ''Name Dropping''
6
7The Chairman of the Board. Ol' Blue Eyes. The Voice. Leader of the Creator/RatPack.
8
9Francis Albert "Frank" Sinatra (December 12, 1915 – May 14, 1998) was one of the best-known and best-loved singers in the history of American popular music. His voice is among the most recognizable in the world, and his work has been featured in numerous other media. An overview of his long and storied career would take too much space, so one should look to [[http://en.wikipedia.org/wiki/Frank_Sinatra The Other Wiki's]] article on him for that. A child of Italian immigrants from UsefulNotes/{{Sicily}} and a native son of UsefulNotes/NewJersey, he's commemorated by his hometown of Hoboken with a large mural covering an entire intersection.
10
11Many historians of music consider Sinatra to have been the true originator of the ConceptAlbum, with [[OlderThanTheyThink 1955]]'s ''Music/InTheWeeSmallHours'' (it's about men feeling lonely and isolated in, well, [[ExactlyWhatItSaysOnTheTin the wee small hours]] of the morning).[[note]]Music/WoodyGuthrie's ''Music/DustBowlBallads'' might also qualify, being as they are all around the central themes of the poverty and hardship suffered by Dust Bowl refugees. There is little debate, however, that ''In the Wee Small Hours'' was the first concept album unified by a mood or musical theme rather than a narrative one.[[/note]] He also had a successful career as an actor -- two of them, in fact. He first made a name for himself on screen as the [[PlayingAgainstType shy, innocent, virginal]] musical performer who costarred with Creator/GeneKelly in ''Film/OnTheTown'' and ''Film/AnchorsAweigh'', and then as the cynical, streetwise tough guy in such movies as ''Film/FromHereToEternity'' (his [[CareerResurrection comeback role]], which won him the [[UsefulNotes/AcademyAward Oscar]] for Best Supporting Actor), ''Film/{{Suddenly}}'', ''Film/TheManWithTheGoldenArm'', and ''Film/TheManchurianCandidate''. Speaking of Oscars, Sinatra also took home the award for Best Original Song three times (and was nominated for two more).
12
13He's also generally believed to have had strong ties to TheMafia, although it's impossible to say just where the truth ends and fantasy begins. One fact most historians agree upon is that working in UsefulNotes/LasVegas and rubbing elbows with guys named "Bugsy" was a package deal in those days. Plus, he was Italian-American (from a UsefulNotes/{{Sicil|y}}ian father and [[UsefulNotes/TheBraveRegionsOfItalia Ligurian]] mother) and born in North Jersey in 1915; it would have been virtually impossible for him ''not'' to have known anyone associated with the Mob. More controversial was his liberal political activism, which got him branded a Communist in some circles. It wasn't until after he had become a registered Republican and sang for [[UsefulNotes/RichardNixon President Nixon]] (largely due to the [[UsefulNotes/JohnFKennedy Kennedy]] family snubbing him) that those rumors finally died down and his career was revitalized.
14
15Furthermore, Sinatra was ''decades'' ahead of the curve regarding race relations. In one case, he forced a hotel to desegregate by announcing that either they would allow Creator/SammyDavisJr (and other black people) to stay there, or he and a number of other members of the Creator/RatPack would not only ''not'' stay there, but they also wouldn't perform there. The pressure applied by him and his fellow Rat Packers were instrumental in causing UsefulNotes/LasVegas to become one of the first cities to fully desegregate.
16
17He was perhaps one of the first performers to induce [[{{Squee}} loud shrills and fainting]] in the female population--or, at least, he [[AstroTurf seemed to be]]. And if some of that was hype, he definitely induced lightheadedness with his generosity; Sinatra was a huge tipper. ''[[NiceToTheWaiter Huge]]''. His minimum tip was $100 -- and this was in the ''[='=]50s''. Today, that's like tipping somebody one thousand dollars. Creator/DonRickles once said, "If you got Sinatra's table, you were buying real estate in Paris the next day." The story goes, he asks the kid who brings his car around outside the restaurant what's the biggest tip he ever got. Kid says $100. Sinatra gives him $200, then asks who gave him the $100 tip. "You did, sir, last week."
18
19He was married four times -- including to Creator/AvaGardner and Creator/MiaFarrow -- and had three children: Music/{{Nancy|Sinatra}}, Frank Jr. and Tina. The former two became singers themselves.
20
21----
22!!Albums on TV Tropes:
23* ''Music/SongsForYoungLovers'' (1954)
24* ''Music/InTheWeeSmallHours'' (1955)
25* ''Music/SongsForSwinginLovers'' (1956)
26* ''Music/MyWay'' (1969)
27
28!!Notable appearances in film:
29* ''Film/AnchorsAweigh'' (1945): A musical film co-starring Creator/GeneKelly (and [[WesternAnimation/TomAndJerry Jerry Mouse]]).
30* ''Film/TheHouseILiveIn'' (1945): A ten-minute short which spoke out against anti-Semitism.
31* ''Film/TheMiracleOfTheBells'' 1948): A Press Agent (Creator/FredMacMurray) tries to drum up interest in an unknown actress.
32* ''Film/TakeMeOutToTheBallGame'' (1949): Another musical co-starring Gene Kelly.
33* ''Film/OnTheTown'' (1949): The last of three musicals co-starring Gene Kelly.
34* ''Film/FromHereToEternity'' (1953): Won him the UsefulNotes/AcademyAward for Best Supporting Actor.
35* ''Film/{{Suddenly}}'' (1954): Featured Sinatra playing an assassin with a high-powered rifle planning to kill the president. Lots of myths surround it: Lee Harvey Oswald supposedly watched it a month prior to the assassination of [[UsefulNotes/JohnFKennedy JFK]] and Sinatra allegedly tried to have the film removed from circulation after the event (though this was later proven untrue). It's now in the public domain.
36* ''Film/TheManWithTheGoldenArm'' (1955): Earned him an Oscar nod for Best Actor.
37* ''Film/GuysAndDolls'' (1955)
38* ''Film/HighSociety'' (1956): with Music/BingCrosby and Creator/GraceKelly.
39* ''Film/PalJoey'' (1957): For which he won a UsefulNotes/GoldenGlobeAward.
40* ''Film/SomeCameRunning'' (1958): with Music/DeanMartin and Creator/ShirleyMacLaine.
41* ''Film/AHoleInTheHead'' (1959)
42* ''Film/NeverSoFew'' (1959)
43* ''Theatre/CanCan'' (1960)
44* ''Film/Oceans11'' (1960): with the rest of the Creator/RatPack.
45* ''[[Film/SergeantsThree Sergeants 3]]'' (1962): with the rest of the Creator/RatPack.
46* ''Film/TheManchurianCandidate'' (1962)
47* ''Film/ComeBlowYourHorn'' (1963): For which he earned a Golden Globe nomination.
48* ''Film/RobinAndTheSevenHoods'' (1964): with Music/DeanMartin, Creator/SammyDavisJr, and Music/BingCrosby.
49* ''Film/MarriageOnTheRocks'' (1965)
50* ''Film/VonRyansExpress'' (1965): Where he was NOT asked to sing!
51* ''Film/AssaultOnAQueen'' (1966)
52* ''Film/TheNakedRunner'' (1967): His behavior behind the scenes turned the film into a disaster, with him walking out in mid-production.
53* ''Film/NoneButTheBrave'' (1965): Sinatra's only film as a director, a World War II drama about American and Japanese soldiers who are stranded on a Pacific Island and forced to cooperate. It was not well-received.
54* ''Film/TheDetective'' (1968): Based on the book of the same name from the novel series that spawned ''Film/DieHard''. When the sequel novel ''Nothing Lasts Forever'' was getting a film adaptation, Sinatra was offered the part due to contract stipulations. Eventually, the adaption morphed into ''Die Hard'' with Creator/BruceWillis as the protagonist, now named John [=McClane=].
55* ''Film/LadyInCement'' (1968)
56* ''Film/DirtyDingusMagee'' (1970)
57* ''Film/TheFirstDeadlySin'' (1980)
58* ''[[Film/TheCannonballRun Cannonball Run II]]'' (1985): A [[TheCameo cameo]] appearance {{as himself}}, reuniting him with fellow Rat Packers Creator/DeanMartin, Creator/SammyDavisJr and Creator/ShirleyMacLaine.
59
60!!Notable appearances on television:
61* ''Series/MagnumPI'': He was apparently a big fan of the show and asked for a guest appearance. Sinatra's 1987 appearance in episode "Laura" was his last acting role.
62* ''Series/WhatsMyLine'': Sinatra had a running feud with ''Line'' panellist Dorothy Kilgallen and refused to appear on the show until after she had died.
63
64!!Appearances in fiction:
65* Frank Sinatra was subject to many parodies in WesternAnimation, particularly during the [[UsefulNotes/TheGoldenAgeOfAnimation Golden Age]]. Such appearances include:
66** Creator/TexAvery's "Little 'Tinker", in which a lonely skunk attempts to woo the other forest creatures by putting on a Frank Sinatra suit and singing "All or Nothing at All". The female bunnies watching all [[LoveMakesYouCrazy go insane at the sight of him]], and while on stage the Sinatra-skunk (in a rather cruel parody of how skinny Sinatra was in the '40s) falls through a knothole, has plasma being injected into him, sings from an iron lung, gets measured for a casket, and stands on a scale and gets out-weighed by a feather, among other things.
67** Similarly, there's the Creator/FrankTashlin ''WesternAnimation/LooneyTunes'' short "WesternAnimation/SwoonerCrooner", in which Sinatra and Music/BingCrosby are portrayed as roosters, singing for a hysterical audience of hens. At one point, the microphone completely obscures the Sinatra-rooster's body, except for the arms and legs.
68** In the Creator/BobClampett ''Looney Tunes'' short "WesternAnimation/BookRevue", Sinatra is portrayed as so thin and frail that he requires a wheelchair and orderly to get around.
69** Creator/ArtDavis' ''Merrie Melodies'' short "Catch as Cats Can" has a Bing Crosby-like parrot convincing an early version of Sylvester the Cat to try to catch and eat a Sinatra-esque canary.
70** At the end of the ''WesternAnimation/{{Popeye}}'' short "Shape Ahoy", after Popeye and Bluto have spent the entire cartoon fighting over Olive Oyl, she falls head over heels for an animated Sinatra.
71** In ''Film/WhoFramedRogerRabbit'', Eddie Valiant accidentally draws a singing sword against Judge Doom, which has Sinatra's face on it singing (appropriately enough) "Witchcraft".
72** Dino Spumoni from ''WesternAnimation/HeyArnold'' is an {{Expy}} (and AffectionateParody) of late-career Sinatra.
73* Johnny Fontane from ''Film/TheGodfather'' is a flagrant NoCelebritiesWereHarmed version.
74** Mario Puzo never confirmed or denied this, but Sinatra himself threatened at least one newspaper that printed the "Fontane was based on Sinatra" theory with a lawsuit if they did not retract the statement. They did, and it was dropped.
75** On one occasion, Sinatra and Puzo were introduced in a restaurant by a mutual friend. When Sinatra realized who Puzo was, he lost his temper and unleashed a torrent of threats and insults. Puzo later said that while he didn't blame Sinatra for his reaction, he refused to apologize or back down.
76** And funnily enough, Sinatra himself was on the shortlist to play Vito Corleone in the film. This would have made the whole scene between him and Fontane hilarious.
77* Similarly, Sinatra had a very memorable [[InvisibleCelebrityGuest offscreen appearance]] in ''ComicStrip/{{Doonesbury}}''. He [[ClusterBleepBomb swears so frequently]] that the censored bleeps struggle to keep up. Sinatra (unamused) was quoted as saying Garry Trudeau is as funny as cancer, which wound up being his '[[AppropriatedAppellation dedication]]' for the book edition.
78-->'''Sinatra:''' Get me your '''[obscene gerund]''' boss, you little '''[anatomically explicit epithet]'''!\
79'''Card Dealer''': ("[[MediumAwareness Obscene gerund?]]")
80* Sinatra was spoofed in a number of ''Series/SaturdayNightLive'' sketches by Creator/JoePiscopo (in the '80s) and Creator/PhilHartman (in the '90s).
81* Sinatra and the Rat Pack feature in a series of mystery novels by Robert Randisi.
82* He and the Creator/RatPack are the inspiration for [[GangOfHats The Chairmen]] of ''VideoGame/FalloutNewVegas'', especially their leader Benny. Their songs "Blue Moon" and "Ain't That a Kick in the Head" play on the radios, and the latter is the name of the very first quest.
83* Harvey [[MeaningfulName Finevoice]], a recurring character on WebVideo/AtopTheFourthWall, a send-up of Vegas-golden-age Sinatra, complete with references to playing "all da rooms in Vegas" and romancing.
84* A fictionalised version of him appeared in [[https://www.youtube.com/watch?v=K5a_v0MP_Fk an episode]] of ''WebVideo/EpicRapBattlesOfHistory'', in a rap battle against Music/FreddieMercury.
85* "Harry Plinkett" (actually Mike Stoklasa) of ''{{WebVideo/RedLetterMedia}}'' is evidently a fan of the Rat Pack and swing music in general. Each of his "Mr. Plinkett" reviews has featured instrumentals from songs popularized by Frank or Dino. The courtship of Anakin Skywalker and Padme is set to the strings of "Nice n' Easy", "My Way" plays over Creator/GeorgeLucas' homages to Creator/RidleyScott, and ''{{Film/Titanic|1997}}'' featured "Strangers in the Night" (in this case, the Peter Hughes cover from ''Film/EyesWideShut''). This is owing to the fact that Plinkett "sold toupees" to the singer at some point in the past.
86* Perfect Cell in ''WebVideo/DragonBallZAbridged'' goes out with "My Way" as his swan song.
87** Future Imperfect Cell ''tried'' to do this too...but he only had about ten minutes of screentime, so he was obliterated before he finished the first line.
88* Vic Fontaine from ''Series/StarTrekDeepSpaceNine'', played by fellow lounge singer James Darren, was heavily inspired by him and sings several of his songs.
89* His ghost serves as a mute spirit advisor to the eponymous ''Literature/OddThomas'' for several books. Odd invokes one of Sinatra's {{berserk button}}s (mentioned below) to get him to go {{poltergeist}} and save Odd's bacon.
90* Each of the games of the ''Videogame/{{Bayonetta}}'' series features a cover of a song sang by Sinatra. The first game has "Fly Me to the Moon", the second game has "Moon River" and the third game has "Moonlight Serenade".
91* His version of Marion Montgomery's "That's Life" appears in the soundtrack for ''VideoGame/TonyHawksUnderground 2'', [[SoundtrackDissonance of all things]]. It is one of two songs used for the end credits (the other one being Music/{{Metallica}}'s "Whiplash").
92
93!!Tropes invoked by him:
94* ActuallyPrettyFunny:
95** His participation in several celebrity roasts showed he wasn't above making fun of himself, especially around friends.
96** Sinatra first met Creator/DonRickles when he wandered into a late-night show of his at the Sands with the entire Rat Pack in tow and Creator/ShirleyMacLaine on his arm. Any one of these people could have ended Rickles' career, but he peered at their table through the darkness and said: "Hey Frank, make yourself at home and punch somebody." He proceeded to riff on the group at length, ending with Sinatra literally on the floor laughing. The two were lifelong friends after that, with Rickles even opening for Frank on several tours and serving as a pallbearer at his funeral.
97* AstroTurf: Those squealing bobbysoxers who made him famous? Actresses hired by his publicist.
98* ChristmasSongs: He recorded a great many of these, and even helped to co-write one ("Mistletoe and Holly").
99** Of particular note is his 1957 recording of "[[Film/MeetMeInStLouis Have Yourself a Merry Little Christmas]]", which was the first to substitute the now-standard lyric "hang a shining star above the highest bough" for the rather darker original "until then we'll have to muddle through somehow". The change came about when Sinatra told composer Hugh Martin, "The name of my album is ''A Jolly Christmas''. Do you think you could jolly up that line for me?"
100* CityShoutOuts: "My Kind Of Town" has a published footnote saying that "Any city name of three syllables can replace Chicago; such as Manhattan, Las Vegas, etc."
101* FriendlyRivalry: With fellow crooner-turned-actor Music/BingCrosby.
102* HaveAGayOldTime: Don't assume Frankie's got the stones when you hear him use the phrase "make love" during songs like ''Night and Day", "You're Sensational", or of course "Mind If I Make Love to You?". It just meant to make small talk with a lover.
103* IAmGreatSong: "My Way", a CoverVersion of "Comme d'habitude" by Music/ClaudeFrancois that totally rewrites the lyrics. Frank went on the record as disliking the song. But it fit his persona so perfectly, he was obliged to top off every concert with it.
104-->"You sing it at every show, you'd hate it, too! Don't gimme that jazz."
105* IncrediblyLongNote: "New York, New York" ends with an extremely long note that lasts until the end of the final stinger:
106-->''It's up to you, New York, NEW YOOOOOOORRRRRRRK!!! NEW YOOOOOOOOOOOOOORRRRRRRRRRRRRRK!!!!!!!!!!!''
107* LetsDuet:
108** He did a few duets with his friend Creator/DinahShore and his friendly rival Creator/BingCrosby.
109** Also did one with his daughter Music/{{Nancy|Sinatra}}, a CoverVersion of "Somethin' Stupid" in 1967.
110* LocationSong: "New York, New York", "Chicago (That Toddlin' Town)", both a {{Homage}} to those cities.
111* LyricalDissonance: The cheery, upbeat "Mack the Knife" tells the story of a notoriously violent and psychopathic gangster.
112* TheNicknamer: According to his valet, Frank had derogatory nicknames for many of his friends, including "Sheeny" for Creator/CaryGrant, "Shanty" for Creator/GeneKelly, "Jew" for Creator/JerryLewis, "The African Queen" for Music/JohnnyMathis, and "Wop" for Music/DeanMartin.
113* SerialSpouse: Married four times.
114* TotallyRadical: 1962's "Everybody's Twistin' " was an attempt to jump on the DanceSensation bandwagon in TheSixties, but it's loaded with slang that went stale around 1939 or so.
115-->A cat who was really hep\
116Put down a step\
117A new gyration\
118Soon, all the kids were twistin'!
119* [[invoked]]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.
120----
121-->''I said all, nothin' at all''
122-->''If it's love, there ain't no in-between''
123-->''Why begin then cry for somethin' that might have been''

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