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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 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 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 costarred 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."

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.
  • 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 Fontaine 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 short list 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.
  • 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.

Tropes invoked by him:

  • 10-Minute Retirement: He "retired" several times beginning in the early 1970s, but it never stuck.
  • 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.
  • Berserk Button: Frank had a legendary short fuse. Some examples:
    • When Woody Allen 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. She said it was a joke in court during their custody battle.
    • Another one with Allen. When Allen allegedly molested his (Allen’s) and Farrow's daughter, he allegedly tried to have a mob hit taken out on him but was told he didn't have the pull to do that anymore.
    • He threatened to have Peter Lawford’s legs broken 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. Sort of.
      "I overreacted. A little."
    • Fairly justified in that Sinatra fell into a terrible depression, and was largely abandoned by the entertainment business and by many fans as a homewrecker and a has-been following his fling with Ava Gardner. Much of the Rat Pack were down-and-out entertainers and friends who took a supportive True Companions-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 (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.
  • Bigger Is Better in Bed: 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 cock."
  • Bishōnen: He was referred to as "The Skinny Kid from Hoboken" and yet made his female fans swoon hard.
  • Born Lucky: A somewhat literal example; because his birth went rough, and he had a high birth weight (13 1/2 pounds), Sinatra was thought to have been stillborn until his grandmother revived him with cold tap water.
    • Oddly enough, he died lucky as well! He had what would turn out to be his fatal heart attack on the same night that the Seinfeld series finale was premiering on the U.S. West Coast. Because everyone was inside watching the show, there was little traffic on the normally busy streets and his ambulance got him to the hospital just in time for him to die comfortably.
  • 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?"
  • Cool Old Guy: Frankie was definitely more likable and suave from The '50s on forward (when he was in his forties), and his tenure with the Rat Pack, and his staying in showbiz into The '90s 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.
  • The Dreaded: One memorable account by Tina Sinatra has a paparazzo snooping around her dad's house, then suddenly finding himself nose-to-nose with the Chairman himself. Terrified, the photographer leapt into a pool (despite being unable to swim), requiring Frank to fish him out.
  • Dude, Where's My Reward?: 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, 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, Bing Crosby. 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.
    Gore Vidal: ...But then no Democratic President asked him to perform at the White House. It was 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 Sammy Davis Jr. to a gala because he was afraid Davis' marriage to a (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.
  • Every Scar Has a Story: 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.
  • 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.
    • You should take into consideration that the last two songs were sung to... Grace Kelly. Rawr!
    • Also, the page image above.
  • He Also Did: Sinatra was hired by Life to photograph the March 8th, 1971 boxing match between Muhammad Ali 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.)
  • "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."
  • Jack of All Trades: 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.
  • 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.
  • Mr. Fanservice: "OH FRANKIE!!" *faint* As you can tell from the sheer number of parodies, he was a Trope Codifier.
  • Nice Hat: One of the few men capable of truly pulling off the fedora.
  • Nice to the Waiter:
    • 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 Bela Lugosi'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 Dr. 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.
  • 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.
  • Papa Wolf: Frank was a man of many flaws, but a neglectful father he was not. When his son Frank Jr. was kidnapped, the elder Sinatra was terrified that he wouldn't have enough dimes on him to use the telephone (the kidnappers insisted on exclusively communicating through payphone), and got in the habit of carrying 10 dimes on him at all times, a habit he would maintain for the rest of his life, and was even buried with 10 dimes in his pocket.
  • Salt and Pepper: 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.
  • Serial Spouse: Married four times.
  • True Companions: The Rat Pack, of course, named after the True Companions 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 YouTube (especially Frankie and Deano), it'll have you rolling in the aisles.
    • In point of fact, as Lauren Bacall, for one, relates in her autobiography, the Rat Pack 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.
  • Your Cheating Heart: His extramarital affairs (especially those during his first marriage) were highly publicized.
    • He was also 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
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