[[caption-width-right:300:''"Ring-a-ding-ding, baby."'']]

->''"He lives by an ancient code -- he's 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]]. Leader of the Creator/RatPack.

Francis Albert Sinatra (December 12, 1915 -- May 14, 1998) is one of the best-known and best-loved singers in the history of American popular music. His music and voice are 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 native son of UsefulNotes/NewJersey, he's commemorated by his hometown of Hoboken 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).[[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 won an [[UsefulNotes/AcademyAward Oscar]] three times (and was nominated for two more) for Best Original Song.
He also had a successful career as an actor -- two, in fact. First, 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 beginning with his [[CareerResurrection comeback role in]] ''Film/FromHereToEternity'' (which won him an Oscar for Best Supporting Actor), ''The Man with the Golden Arm'', and ''Film/TheManchurianCandidate''.

He 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 UsefulNotes/LasVegas and rubbing elbows with guys named "Bugsy" was a package deal in those days. Plus, he was Italian American 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 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.

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, they wouldn't perform there, either. The pressure applied by him and his fellow Rat Packers was instrumental in causing UsefulNotes/LasVegas 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]]. 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 -- back in the ''Fifties''. 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." 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]]
* ''Film/TheHouseILiveIn'': 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.
* ''Film/TheManWithTheGoldenArm''
* ''Film/GuysAndDolls''
* ''Film/HighSociety'' with Music/BingCrosby and Creator/GraceKelly
* ''Film/PalJoey''
* ''Film/SomeCameRunning'' (1958)
* ''A Hole in the Head''
* ''Film/Oceans11'' with the rest of the Creator/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.
* ''Film/NoneButTheBrave'': 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.
* ''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 Creator/BruceWillis 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'' panellist Dorothy Kilgallen 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 [[UsefulNotes/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, "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.
** In the Creator/BobClampett ''WesternAnimation/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 ''WesternAnimation/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.
** 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.
** And funnily enough, Sinatra was on the short list to play Vito Corleone. This would have made the whole scene between him and Fontane hilarious.
* 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 [[foldercontrol]]

[[folder: [obscene gerund ]]
] boss, you little [[/folder]]

[[folder: [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 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.
* 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" (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.
* Vic Fontaine from ''Series/StarTrekDeepSpaceNine'', played by fellow lounge singer James Darren, was heavily inspired by him and sings several of his songs.

!!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 Creator/RayLiotta'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 Creator/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.
** Here's a strange chapter of bad blood in show business: The Unknown Comic ([[Series/TheGongShow remember him?]]), aka Murray Langston, offhandedly cracked a joke about Frank during a special appearance on 1990s game show ''Make Me Laugh,'' and apparently Frank responded by calling Langston at his house, threatening to break his bones. Langston didn't even believe it was him at first, till ''Milton Berle'' called him and confirmed it.
* BiggerIsBetterInBed: Creator/AvaGardner 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 cock."
* {{Bishonen}}: He was referred as "The Skinny Kid from Hoboken" and yet made his female fans swoon hard.
* 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?"
* 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 ''Film/TheHouseILiveIn''.
** 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 BackAlleyDoctor 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.
* 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 [[Film/HighSociety 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, he was obliged to top off every concert with it.
-->"You sing it at every show, you'd hate it, too! Don't gimmie that jazz."
* 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 the big bands of Harry James and Tommy Dorsey, he was also extremely good at fine-tuning his musicians and technicians.
* LocationSong: "New York, New York", "Chicago (That Toddlin' Town)", both a {{Homage}} to those cities.
* LyricalDissonance: The cheery, upbeat "Mack the Knife" tells the story of a notoriously violent and psychopathic gangster.
* MrFanservice: "OH FRANKIE!!" *faint* As you can tell from the sheer number of parodies, he was a TropeCodifier.
* NiceHat: One of the few men capable of truly pulling off the fedora.
* 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.
** He was known to be extremely generous (for instance, he paid for Creator/BelaLugosi's funeral when the actor died in poverty) and was fiercely loyal to his friends. Among other things, he refused to perform in any hotel that wouldn't serve Sammy Davis Jr., effectively ending racial discrimination in Las Vegas hotels in the process.
** He was also a big supporter of racial equality and the Civil Rights movement, at a time period where segregation was still a very real and dominant presence in the US. Sinatra performed numerous concerts to support activists like Martin Luther King Jr. And it wasn't just that he wouldn't step into hotels that wouldn't allow Sammy Davis Jr. He wouldn't support any hotel that refused to allow any African American to enter. He even wrote an article in Ebony Magazine explaining that, to him, race is not an issue.
* 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.
* SaltAndPepper: 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.
* SerialSpouse: Married four times.
* 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 Creator/LaurenBacall, for one, relates in her autobiography, the Creator/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.
* 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.
-->''I said all, nothin' at all''
-->''If it's love, there ain't no in-between''
-->''Why begin then cry for somethin' that might have been''
-->''No I'd rather, rather have nothin' at all''