Before he became (arguably) the most famous singer of the 20th century, Frank Sinatra was raised in New Jersey, where he had direct family connections to organized crime. His godfather (not the metaphoric movie kind, his actual godfather) was Guarino “Willie” Moretti, an underboss for the Genovese crime family who used his criminal influence to help a young Sinatra book singing gigs. He also allegedly used force to help extricate Sinatra from an early, unfavorable contract with famed band leader Tommy Dorsey when the crooner started getting big.
The FBI even had a file on Sinatra, who allegedly bragged about knowing infamous criminals like Bugsy Siegel. So it’s perhaps understandable that, when the story circulated that Frank Sinatra used his mafia connections to nab a serious dramatic role, in an adaptation of an acclaimed, award-winning, best-selling novel, people were willing to believe it. After all, this was a singer whose previous films were mostly song-and-dance comedies. Some of them were pretty danged good — “On the Town” is a classic, and his buddy musical with Gene Kelly, “Anchors Aweigh” was nominated for Best Picture — but casting him in such a plum part probably raised eyebrows.
Then again, those eyebrows may have lowered when people saw the film and realized ‘holy cow, Sinatra can really act,’ or at least after he won the Academy Award for Best Supporting Actor. Especially since he beat out some hefty competition, including Eddie Albert in “Roman Holiday,” Robert Strauss in “Stalag 17,” and Jack Palance and Brandon deWilde, both from “Shane.”