Summary

  • Organized crime, womanizing, and kidnappings - Frank Sinatra's life story is as unforgettable as the songs he sang.
  • Sinatra's friendships with notable figures like JFK and Joe DiMaggio added more twists to his already fascinating life.
  • Martin Scorsese has created unusual biopics in the past, and Sinatra could be his most fascinating subject yet.

Martin Scorsese is reportedly developing a Frank Sinatra biopic with Leonardo DiCaprio set to star, and there are some incredible stories from the crooner's life that should be included. Most music biopics are fairly tame affairs targeted toward fans, but Frank Sinatra led such a remarkable life that his story is one that's begging to be told. Martin Scorsese has proven before that he's a master of unorthodox biopics with movies like The Wolf of Wall Street and The Aviator, and a Sinatra biopic could continue this trend.

Martin Scorsese's Frank Sinatra biopic has plenty of material to choose from. Sinatra rose from humble beginnings to become one of the biggest stars in the world, but his life was plagued by controversies surrounding his relationships and his alleged ties to organized crime. He's such a towering figure in American pop culture that it's often hard to tell which stories about him are true and which are merely Hollywood myths. Some stories about Sinatra are outrageous and farcical, while others reveal the tragic inner turmoil of the great entertainer.

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10 Frank Sinatra's Ties To The Mob

Sinatra's godfather was a notorious gangster, and he spent time with other famous criminals

The FBI was concerned enough about Sinatra's ties to the mob that they kept extensive records on him throughout most of his life.

Frank Sinatra always denied that he was involved in organized crime in any way, but he had many links to Italian-American gangsters. His godfather was an underboss of the Genovese crime family, and he reportedly grew close to several other criminals throughout his life. Sinatra allegedly befriended the likes of Lucky Luciano, Sam Giancana and Mickey Cohen, among others.

The FBI was concerned enough about Sinatra's ties to the mob that they kept extensive records on him throughout most of his life. Sinatra was persistently followed by rumors that the mob had used some of their influence to help him along in his career, especially when he got out of his contract with big band leader Tommy Dorsey so that he could pursue a solo career on his own terms. Sinatra also famously attended the Mafia Havana Conference in 1946.

9 Frank Sinatra's Friendship With John F. Kennedy

Sinatra may have helped JFK get into the White House

Although they fell out and stopped talking, Sinatra cried for days after JFK's death, according to his daughter Nancy.

One element of Sinatra's life which made his ties to organized crime even more unusual was his relationship with President Kennedy. It's unclear when the two first met, but Sinatra and Kennedy spent plenty of time together throughout the late 1950s. Kennedy's sister married Rat Pack actor Peter Lawford, so it's possible that this connection started their friendship. Sinatra publicly supported Kennedy when he made a run for the White House in 1960.

Despite their shared love of partying and beautiful women, Sinatra's relationship with Kennedy eventually soured. Jackie Kennedy reportedly wanted her husband to stay far away from the singer, and his ties to the mob may have also contributed to him being banned from the White House. Although they fell out and stopped talking, Sinatra cried for days after JFK's death, according to his daughter Nancy. Years later, he even shared a dinner with Jackie Kennedy, possibly to bond over their shared grief.

8 Frank Sinatra Was A Notorious Womanizer

Sinatra was married four times, but he had many affairs