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"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
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The Chairman of the Board. Ol' Blue Eyes. The Voice. Leader of the Rat Pack.

Francis Albert "Frank" 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 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 The Other Wiki's article on him for that. A child of Italian immigrants from Sicily and a native son of New Jersey, he's commemorated by his hometown of Hoboken with a large mural covering an entire intersection.

Interestingly, serious historians of music consider Sinatra to be the true inventor of the Concept Album, with 1955's In the Wee Small Hours (it's about men feeling lonely and isolated in, well, the wee small hours of the morning).note  He also had a successful career as an actor — two, in fact. First, as the shy, innocent, virginal musical performer who co-starred with Gene Kelly in On the Town and Anchors Aweigh, and then as the cynical, streetwise tough guy in From Here to Eternity (his comeback role, which won him an Oscar for Best Supporting Actor), The Man with the Golden Arm, and The Manchurian Candidate. Speaking of Oscars, he also took home the award for Best Original Song three times (and was nominated for two more).

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He's also generally believed to have had strong ties to The Mafia, although it's impossible to say where the truth ends and fantasy begins. One fact most historians agree on is that working in Las Vegas 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 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 Sammy Davis Jr. (and other black people) to stay there, or he and a number of other members of the Rat Pack would not only not stay there, but they also wouldn't perform there either. The pressure applied by him and his fellow Rat Packers were instrumental in causing Las Vegas to become one of the first cities to fully desegregate.

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Perhaps one of the first performers to induce loud shrills and fainting in the female population—or, at least, he seemed to. And if some of that was hype, he definitely induced lightheadedness with his generosity — Sinatra was a huge tipper. Huge. His minimum tip was $100 — back in the Fifties. Today, that's like tipping somebody one thousand dollars. Don Rickles 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."

He's had three children — Nancy, Frank Jr. and Tina. The former two became singers.


Notable albums

Notable appearances in Film

Notable appearances on Television

  • Magnum, P.I.: 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.
  • What's My Line?: 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 Western Animation during its Golden Age. Such appearances include:
    • Tex Avery'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 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 Frank Tashlin Looney Tunes short, "Swooner Crooner", in which Sinatra and Bing Crosby 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 Bob Clampett Looney Tunes short, Book Revue, Sinatra is portrayed as so thin and frail that he requires a wheelchair and orderly to get around.
    • In Who Framed Roger Rabbit, 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 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 Hey Arnold! is an Expy (and Affectionate Parody) of late-career Sinatra.
  • Johnny Fontane from The Godfather is a flagrant No Celebrities Were Harmed 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 shortlist to play Vito Corleone. This would have made the whole scene between him and Fontane hilarious.
  • Similarly, Sinatra had a very memorable offscreen appearance in Doonesbury. He 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 'dedication' for the book edition.
    Sinatra: Get me your [obscene gerund] boss, you little [anatomically explicit epithet]!
    Card Dealer: ("Obscene gerund?")
  • Sinatra and the Rat Pack feature in a series of mystery novels by Robert Randisi.
  • He and the Rat Pack are the inspiration for The Chairmen of Fallout: New Vegas, 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 Finevoice, a recurring character on Atop the Fourth Wall, 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 an episode of Epic Rap Battles of History, in a rap battle against Freddie Mercury.
  • "Harry Plinkett" (actually Mike Stoklasa) 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 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 George Lucas' homages to Ridley Scott, and Titanic featured "Strangers in the Night" (in this case, the Peter Hughes cover from Eyes Wide Shut). This is owing to the fact that Plinkett "sold toupees" to the singer at some point in the past.
  • Perfect Cell in Dragon Ball Z Abridged goes out with "My Way" as his swan song.
    • 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.
  • Vic Fontaine from Star Trek: Deep Space Nine, played by fellow lounge singer James Darren, was heavily inspired by him and sings several of his songs.
  • His ghost serves as a mute spirit advisor to the eponymous Odd Thomas for several books. Odd invokes one of Sinatra's berserk buttons (mentioned below) to get him to go poltergeist and save Odd's bacon.

Tropes invoked by him:

  • Actually Pretty Funny:
    • His participation in several celebrity roasts showed he wasn't above making fun of himself, especially around friends.
    • Sinatra first met Don Rickles when he wandered into a late-night show of his at the Sands with the entire Rat Pack in tow and Shirley MacLaine 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.
  • AstroTurf: Those squealing bobbysoxers who made him famous? Actresses hired by his publicist.
  • Christmas Songs: 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?"
  • Have a Gay Old Time: 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.
  • "I Am Great!" Song: "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."
  • Let's Duet:
  • Location Song: "New York, New York", "Chicago (That Toddlin' Town)", both a Homage to those cities.
  • Lyrical Dissonance: The cheery, upbeat "Mack the Knife" tells the story of a notoriously violent and psychopathic gangster.
  • The Nicknamer: According to his valet, Frank had derogatory nicknames for many of his friends, including "Sheeny" for Cary Grant, "Shanty" for Gene Kelly, "Jew" for Jerry Lewis, "The African Queen" for Johnny Mathis and "Wop" for Dean Martin.
  • Serial Spouse: Married four times.
  • invokedWhat Could Have Been: He was asked if he could perform the main theme for the James Bond film You Only Live Twice and declined. His daughter Nancy ended up with the gig.

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
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