One of Sinatra’s childhood nicknames was “Scarface”:

Sinatra hated to be photographed from his left side. He weighed 13 ½ pounds at birth and bore the forceps scars for the rest of his life. Sinatra had a scar from the left corner of his mouth to his jaw line, and a cauliflower ear.

The bad-boy image from his infamous 1938 mug shot was caused by an arrest for…seduction:

Sinatra’s first tabloid moment erupted when one of his girlfriends attacked his soon-to-be-wife (Nancy) at a nightclub and later had him arrested not once (for seduction), but twice (for adultery)!

Sinatra’s first publicist – George Evans – auditioned girls for how loud they could scream and placed them in the audience at Sinatra’s shows:

Evans would rehearse with the girls and offer timed screaming cues throughout the playlist. He would give them a five-dollar-bill to ensure that they would stay for at least five of Sinatra’s shows.

The Godfather’s Johnny Fontane character was based on Sinatra even though he denied it:

In the novel, Puzo relates how the fictional bandleader Les Halley (Tommy Dorsey) pressures the fictional singer Johnny Fontane (Sinatra) into an impossibly severe personal-services contract. Fontane approaches his godfather to intervene and after putting a pistol to Halley’s head, Corleone gets the singer released from his contract. Sinatra refused to acknowledge the portrayal, but Jerry Lewis asserts that the Mafia did approach Dorsey with “an offer he couldn’t refuse.”

Sinatra was accused of dodging the draft in WWII:

Sinatra was disqualified from service in WWII (for a busted eardrum, mastoids, and emotional instability). A controversy erupted when a story surfaced that Sinatra was under FBI investigation for reportedly paying doctors $40,000 to declare him unfit to serve.

Sinatra was a humanitarian who hated intolerance:

Sinatra had encountered far too many black geniuses to feel anything but pity and contempt for racist America. In the throes of racial tension, Sinatra spoke of the importance of education and how he had suffered racial intolerance – as an Italian-America – back home in New Jersey. He even made a short film, The House I Live In (1945), to oppose anti-Semitism and prejudice at the end of World War II, for which he was awarded an honorary Oscar.

J. Edgar Hoover started his 1,275 page FBI Sinatra dossier in the 1940s…because a fan compared Sinatra to Hitler in a letter to the FBI:

Hoover’s Sinatra obsession began after a radio listener wrote to the FBI and said “the other day I turned on a Frank Sinatra program and I thought how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass-hysteria!”

Sinatra and Columbia Records created the first thematic album of popular music available to the American public in 1946:

Even though Sinatra’s singing could be heard on the radio and in concert, it was a time when the notion of a phonograph album was new and exotic. The first Sinatra box set, with four records inside, sold for the not inconsiderable price of $2.50, the equivalent of $30 today. And the people bought it by the tens of thousands.

Sinatra tried killing himself at the lowest point in his career:

His power usurped by Perry Como and newcomer Eddie Fisher – Sinatra tried to kill himself in February of 1951. Sinatra was walking through Times Square when he saw giant crowds of girls beneath Fisher’s Paramount marquee. Reminded of his past fame, and fall from fortune, Sinatra went back to his suite, laid his head on the stove, and turned on the gas. His A&R manager found him lying on the floor, sobbing. It was his third attempt at suicide.