->''"He lives by an ancient code -- he's [[SugarAndIcePersonality unforgiving of his enemies, protective of his friends]]."''
-->-- '''Alan King''', ''Name Dropping''

[[RedBaron The Chairman of the Board]]. [[FanNickname Ol' Blue Eyes.]] [[SpellMyNameWithAThe The Voice.]]

Francis Albert Sinatra (December 12, 1915 -- May 14, 1998) is one of the best known and best loved singers in the history of popular music. (He was also a pretty popular and acclaimed actor.) His music and voice are some of 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 native son of NewJersey, his hometown of Hoboken honors him with a large mural covering an entire intersection.

Interestingly, serious historians of music consider him to be the true inventor 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). He also won an [[AcademyAwards Oscar]] three times (and was nominated for two more) for Best Original Song.

Also probably had strong ties to TheMafia, although it's impossible to say where the truth ends and fantasy begins. One fact most historians agree on is that working in Vegas and rubbing elbows with guys named "Bugsy" was a package deal in those days. More controversial was his political activism, which branded him a Communist in some circles. It wasn't until he became a registered Republican and sang for [[UsefulNotes/RichardNixon President Nixon]] (largely due to the Kennedy family snubbing him) that those rumors died down and his career revitalized.

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 Sammy Davis Jr. (and other black people) to stay there, or he and a number of other members of the RatPack would not only ''not'' stay there, they wouldn't perform there, either. The pressure applied by him and his fellow Rat Packers was instrumental in causing [[VivaLasVegas Las Vegas]] to become one of the first cities to fully desegregate.

Perhaps one of the first performers to induce [[{{Squee}} loud shrills and fainting]] in the female population - or, at least, he [[AstroTurf seemed to]].

Was a huge tipper. ''[[NiceToTheWaiter Huge]]''. His minimum tip was $100 -- back in the ''Fifties''. Today, that's like tipping somebody one thousand dollars. DonRickles once said, "If you got Sinatra's table, you were buying real estate in Paris the next day." 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."

!! Notable albums
* ''Music/SongsForYoungLovers'' (1954)
* ''Music/InTheWeeSmallHours'' (1955)
* ''Music/SongsForSwinginLovers'' (1956)
* ''Music/MyWay'' (1969)

!!Notable appearances in Film
* ''Film/AnchorsAweigh'': Alongside Creator/GeneKelly and [[WesternAnimation/TomAndJerry Jerry]]
* ''The House I Live In'': A ten minute short which spoke out against anti-Semitism.
* ''Take Me Out To The Ball Game'' : Another film co-starring Gene Kelly.
* ''Film/OnTheTown'': The last of three musicals co-starring Gene Kelly.
* ''Film/FromHereToEternity'': Won the Oscar for Best Supporting Actor.
* ''Suddenly'': Featured Sinatra playing an assassin with a high-powered rifle planning to kill the president, well known both for Lee Harvey Oswald having supposedly watched it a month prior to the assassination of Kennedy and because Sinatra tried to have the film removed from circulation after the event. Now in the public domain.
* ''The Man with the Golden Arm''
* ''Film/GuysAndDolls''
* ''Film/HighSociety'' with BingCrosby and Creator/GraceKelly
* ''Pal Joey''
* ''A Hole in the Head''
* ''Film/OceansEleven'' with the rest of the RatPack
* ''Film/TheManchurianCandidate''
* ''Robin and the 7 Hoods''
* ''Film/VonRyansExpress'': Where he was NOT asked to sing!
* ''The Naked Runner'': His behavior behind the scenes turned the film into a disaster, with him walking out in mid-production.
* ''TheDetective'': Based on the book of the same name from the novel series that spawned ''Film/DieHard''. When the sequel novel ''Nothing Last Forever'' was getting a film adaptation, there were talks of casting Sinatra for the part. Eventually the adaption of NLF morphed into the first Die Hard film and Bruce Willis was given the role.

!!Notable appearances on Television
* ''Series/MagnumPI'': He was apparently a big fan of the show and asked for a guest appearance.
* ''Series/WhatsMyLine'' : Sinatra had a running feud with ''Line'' panelist Dorothy Kilgalian and refused to appear on the show until after she had died.

!! Appearances in Fiction
* Frank Sinatra was subject to many parodies in WesternAnimation during its [[TheGoldenAgeOfAnimation Golden Age]]. Such appearances include:
** 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 (in a rather cruel parody of how skinny Sinatra was in the late '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.
** Similarly, there's the Creator/FrankTashlin ''WesternAnimation/LooneyTunes'' short, ''Swooner Crooner,'' 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.
** In the Creator/BobClampett ''LooneyTunes'' short, ''WesternAnimation/BookRevue,'' Sinatra is portrayed as so thin and frail that he requires a wheelchair and orderly to get around.
** In ''Film/WhoFramedRogerRabbit'', Eddie Valiant accidentally draws a singing sword against Judge Doom, which has Sinatra's face on it singing (appropriately enough) "Witchcraft".
** In one installment of WesternAnimation/{{Popeye}}, after Popeye and Bluto spend the entire episode fighting over Olive Oyl, in the end she falls head over heels for (an animated) Frank Sinatra.
** Dino Spumoni from HeyArnold is an {{Expy}} (and AffectionateParody) of late-career Sinatra.
* Johnny Fontaine from ''Film/TheGodfather'' is a flagrant NoCelebritiesWereHarmed version.
** 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.
* 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.
-->'''Sinatra:''' Get me your [[AC:[obscene gerund]]] boss, you little [[AC:[anatomically explicit epithet]]]!\\
'''Card Dealer''': ("[[MediumAwareness Obscene gerund?]]")
* Sinatra and the Rat Pack feature in a series of mystery novels by Robert Randisi.
* He and the 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.
* 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.
* A fictionalised version of him appeared in [[http://www.youtube.com/watch?v=K5a_v0MP_Fk an episode]] of ''WebVideo/EpicRapBattlesOfHistory'', in a rap battle against [[Music/{{Queen}} Freddie Mercury]].
* Harry Plinkett of ''{{RedLetterMedia}}'' is evidently a fan of the Rat Pack and swing music in general. Each of his "Mr. Plinkett" reviews has featured instrumentals from a song by Frank or Dino. The courtship of Anakin Skywalker and Padme is set to the strings of "Nice n' Easy", "My Way" plays over George Lucas' homages to Creator/RidleyScott, and ''Titanic'' 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.

!!Tropes invoked by him:
* TenMinuteRetirement: He "retired" several times beginning in the early 1970s, but it never stuck.
* AstroTurf: Those squealing bobbysoxers who made him famous? Actresses hired by his publicist.
* BerserkButton: Frank had a legendary short fuse. Just one example: when Creator/WoodyAllen was found to have been, er, behaving inappropriately with his girlfriend's adopted daughter, Frank called Mia Farrow (the girlfriend and one of Frank's ex-wives) and offered to have Woody's legs broken.
** He threatened to do the same to Peter Lawford for taking Ava Gardner to dinner, despite it being a press junket for a movie they were in. This was included in the film ''The Rat Pack'', with Ray Liotta's Frank offering apologies. [[BackhandedApology Sort of]].
--->"I overreacted. A little."
** [[JustifiedTrope Fairly justified]] in that Sinatra [[HeroicBSOD fell into a terrible depression]], and was [[WhiteDwarfStarlet largely abandoned by the entertainment business]] [[ContractualPurity and by many fans]] [[YourCheatingHeart as a homewrecker]] and a [[PopularityPolynomial has-been]] following his fling with Creator/AvaGardner. Much of the RatPack were down-and-out entertainers and friends who took a supportive TrueCompanions-like stance with each other to help each other bounce back from their situations and ensure they would not be messed with.
* BiggerIsBetterInBed: Ava Gardner got together with Sinatra at a point where his career appeared to be over, and was asked by a reporter what she wanted with a "119-pound has-been." She answered: "Well, honey, I'll tell you - 19 pounds is c***.
* BornLucky: A somewhat literal example; because his birth went rough, and he had a high birth weight (13 1/2 pounds), Sinatra was thought to been stillborn until his grandmother revived him with cold tap water.
** Sinatra ''died'' lucky as well. When he suffered the heart attack that would kill him, it happened to occur at the same time the ''Series/{{Seinfeld}}'' series finale was premiering on the U.S. West Coast. Most people in Los Angeles were inside watching the show, meaning there was very little traffic on the normally busy streets. His ambulance was able to get him to the hospital very quickly because of that.
* ChristmasSongs: He recorded a great many of these, and even helped to co-write one ("Mistletoe and Holly").
** Of particular note is his 1957 recording of "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?"
* CombatPragmatist: Sinatra was this with regard to his own voice. When he was young, he had a relatively weak voice but he compensated by emulating BingCrosby and becoming a master of mic control. As he became middle-aged, his voice deepened and he changed his singing style to compensate; for those who prize his Capitol-era recordings above the others, this was when he [[GrowingTheBeard grew the beard]]. All the way along, whenever his voice changed, he made the change his own rather than fight against it. The result was that he had an exceptionally long career.
* CoolOldGuy: Frankie was definitely more likeable and suave from TheFifties on forward (when he was in his forties), and his tenure with the Rat Pack, and his staying in showbiz ''into TheNineties'' was pretty badass (even if his voice and skills were deteriorating). When he first broke into showbiz in the '30s, he seemed like just another big band singer.
* TheDreaded: One memorable account by Tina Sinatra has a papparazzo snooping around her dad's house, then suddenly finding himself nose-to-nose with the Chairman himself. Terrified, the photographer leaped into a pool (despite being unable to swim), requiring Frank to fish him out.
* DudeWheresMyReward: Another example of Frank's legendary temper: When [=JFK=] was president he planned a trip to Los Angeles and was going to stay at Frank's house as a "thank you" for campaigning in support of him. Frank immediately began construction of a helicopter pad outside his house to accommodate the president. But the president's brother, [[UsefulNotes/RobertFKennedy Bobby Kennedy]], talked [=JFK=] out of it, feeling that it would be a bad political move for the president to stay at the home of a man with known mafia connections. [=JFK=] canceled and instead chose to stay at the home of Sinatra's biggest rival, Music/BingCrosby. The horror! When Sinatra found out he was ''furious'', and immediately grabbed a sledgehammer and began demolishing the newly-constructed helipad. After that incident Frank not only abandoned his support of Kennedy, he abandoned his support of Kennedy's entire ''party'' and became a Republican.
-->'''Creator/GoreVidal:''' ''"...But then no Democratic President asked him to perform at the White House. It was [[TheChessmaster sly old Nixon]], whose House committee had smeared him, who asked Sinatra to perform "The House I Live In'."''
** As a point of trivia, Kennedy would later go 2-for-2 by disinviting SammyDavisJr to a gala because he was afraid Davis' marriage to a ([[MalignedMixedMarriage white]]) Scandinavian actress would hurt his election chances. This led Sammy to defect from the party and go stump for Nixon, as well. Not a promising start for the Kennedy administration.
* EveryScarHasAStory: Frank was delivered clumsily, with forceps, by a {{back alley doctor}} which resulted in a cleft running from his ear to the jawline. But that's not the extent of it: the cartilage of his left ear was mashed, giving the appearance of "cauliflower ear." Sinatra later told his daughter Nancy that when he was eleven, after some playmates began to call him "Scarface," he stormed over to the house of the physician who had delivered him. Fortunately, the doctor wasn't home, and a singing career wasn't abruptly canceled on account of murder.
* MrFanservice: "OH FRANKIE!!" *faint* As you can tell from the sheer number of parodies, he was a TropeCodifier.
* HaveAGayOldTime: Don't think Frankie's got the stones when you hear the phrase "make love" during ''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.
** You should take into consideration that the last two songs were sung to... Creator/GraceKelly. Rawr!
** Also, the page image above.
* IAmGreatSong: "My Way." Frank went on the record as disliking the song, but it fit his persona so perfectly that he was obliged to top off every concert with it.
* JackOfAllTrades: Some music aficionados don't see him as the best in any particular field, but agree that he was extremely talented and a great singer in each field he performed in. Owing to his time with Goodman, he was also extremely good at fine-tuning his musicians and technicians.
* JerkWithAHeartOfGold: See "Berserk Button" above, then listen to Jill St. John, Angie Dickinson, Creator/ShirleyMacLaine, Patty Duke, Doris Day, Juliet Prowse, etc. etc. etc. etc. talk about how Frank was always a perfect gentleman to the ladies. Mia Farrow called Sinatra "sweet", twenty years after their divorce.
** It's widely thought that Creator/AvaGardner was the great love of Sinatra's life. They remained close all their lives even after the divorce, and when heard she was sick (with her final illness) in 1990, he arranged for his own doctors to see her. Being in poor health himself at the time, he couldn't get to her funeral in North Carolina, but made sure that a prominent floral tribute was there.
** NiceToTheWaiter: Studio musicians adored him. Accounts by people who worked with him agree that although he didn't exactly gush with praise for people's performances, he was an absolutely focused professional who knew exactly what he wanted and was quick to express his satisfaction when he got it. There are also various stories of him being generous with money to musicians who were in trouble.
* NiceHat: One of the few men capable of truly pulling off the fedora.
* OldShame: ''The Kissing Bandit'', a very silly musical he didn't even have a choice of being in.
* SerialSpouse: Married four times.
* ThePrimaDonna[=/=]WagTheDirector: Frank Sinatra the ''actor'' was a bit of a handful as kept demanding only one take per scene. The first attempt felt the most genuine, so why bother with another? This was mostly true of his vanity projects (''Ocean's Eleven'') or brief cameo appearances, such as in ''Cannonball Run''.
* TomHanksSyndrome: In the '40s, he played a culture-shocked sailor in ''Anchors Aweigh'' and ''Film/OnTheTown''. Hoping to finally earn top billing, he campaigned for the role of Sky Masterson in ''Film/GuysAndDolls'', but was railroaded into playing Nathan Detroit (yet another ButtMonkey), to his vocal frustration. This began to change in 1953's ''Film/FromHereToEternity'', which reignited his career: he played a loose-cannon Army private. In 1955's ''Film/TheManWithTheGoldenArm'', he plays a fresh-out-of-prison ''drug addict'', in an era where the topic was [[UsefulNotes/TheHaysCode highly controversial]], no less.
** And don't get us started on his collaborations with The RatPack. No wonder the FBI thought he had ties to TheMafia.
** Let's also not forget ''Literature/TheManchurianCandidate''. He carried the whole movie, and not a single song or martini to be found.
* TrueCompanions: The Rat Pack, of course, named after the TrueCompanions of another Hollywood legend, Humphrey Bogart. Sinatra was the founder, and its other chief members were Dean Martin, Sammy Davis Jr., Joey Bishop, and Peter Lawford. If you ever find a clip featuring one of their songs or skits on Website/YouTube ([[http://www.youtube.com/watch?v=gAqyBXFGcUY especially Frankie and Deano]]), it'll have you rolling in the aisles.
** In point of fact, as LaurenBacall, for one, relates in her autobiography, the RatPack was in fact the same group that Bogart led; Sinatra was part of it. Sinatra simply took over the leadership position after Bogie died and transformed it into the more famous version.
** CreatorBacklash: Sinatra reportedly disliked his clique being named "Rat Pack", and insisted that Bogart's group was the only true "Rat Pack". He preferred the the name of "The Summit".
** When Sinatra made it clear the Summit wouldn't patronize any hotels or casinos that wouldn't admit Sammy, segregation in Las Vegas pretty much vanished.
* WhatBeautifulEyes: He was nicknamed "Ol' Blue Eyes" after all.
* WhatCouldHaveBeen: Was offered the role of [[DirtyHarry Harry Callahan]], but broke his wrist and couldn't do it.
* YourCheatingHeart: His extramarital affairs (especially those during his first marriage) were highly publicized.
** He was also [[http://www.thesmokinggun.com/mugshots/celebrity/music/frank-sinatra arrested once]] for having an affair with a married woman.