Frank Sinatra

The Chairman of the Board. Ol' Blue Eyes. The Voice.

Francis Albert Sinatra (1915-1998) is one of the best known and best loved singers in the history of popular music. (And a pretty damn good actor, too.) 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 The Other Wiki's article on him for that. A native son of New Jersey, 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 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). He also won an Oscar three times (and was nominated for two more) for Best Original Song.

Also probably had strong ties to The Mafia, although it's impossible to say where the truth ends and fantasy begins.

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, they wouldn't perform there, either. The pressure applied by him and his fellow Rat Packers was instrumental in causing Las Vegas to become one of the first cities to fully desegregate.

Perhaps one of the first performers to induce loud shrills and fainting in the female population - or, at least, he seemed to.

If a trope is ever written about someone who tips big, really big, it should be called "The Sinatra". His minimum tip was $100 -- back in the Fifties, when people might take home $100 every couple of weeks. 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 appearances in Film

 * Anchors Aweigh: Alongside Gene Kelly and 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.
 * From Here to Eternity: Won the Oscar for Best Supporting Actor.
 * The Man With The Golden Arm
 * Guys and Dolls
 * High Society with Bing Crosby and Grace Kelly
 * Oceans Eleven with the rest of the Rat Pack
 * A Hole In The Head
 * The Manchurian Candidate
 * The Naked Runner: His behavior behind the scenes turned the film into a disaster, with him walking out in mid-production.
 * 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.
 * Von Ryans Express

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.
 * There was another cartoon where something similar was pulled off by a chicken, who at one point, he is completely obscured by the microphone (except for the arms and legs).
 * In Who Framed Roger Rabbit, Eddie Valliant 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.
 * 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.
 * 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.

Tropes invoked by him:

 * Ten Minute Retirement: 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.
 * Berserk Button: Frank had a legendary short fuse. Just one example: 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.
 * 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.
 * Blue Eyes: Obviously.
 * 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 been stillborn until his mother 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 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.
 * Cool Old Guy: Frankie was definitely more likeable and suave from The Fifties on forward (when he was in his forties), and his tenure with the Rat Pack, and his staying in showbiz into The Nineties was pretty badass (even if his voice and skills were deteriorating). When he first broke into showbiz in the '40s, he seemed like just another pop singer.
 * Mr. Fanservice: "OH FRANKIE!!" *faint* As you can tell from the sheer number of parodies, he was a Trope Codifier.
 * 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.
 * Jerk With a Heart of Gold: See "Berserk Button" above, then listen to Jill St. John, Angie Dickinson, Shirley MacLaine, 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 Ava Gardner 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.
 * 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.
 * Nice Hat: One of the few men capable of truly pulling off the fedora.
 * Took a Level In Badass: In the '40s, he played a singing and dancing sailor in Anchors Aweigh and On The Town. In 1953's From Here To Eternity (which reignited his career) he played a loose-cannon Army private, and in 1955's The Man With The Golden Arm, he plays a fresh-out-of-prison drug addict, in an era where the topic was highly controversial, no less.
 * And don't get us started on his collaborations with The Rat Pack. No wonder the FBI thought he had ties to The Mafia.
 * Let's also not forget The Manchurian Candidate.
 * 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.
 * Creator Backlash: 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.