10 Storylines We Need To See In Martin Scorsese's Frank Sinatra Biopic

April 24, 2024, 4:15 p.m.

Movies

10 Storylines We Need To See In Martin Scorsese's Frank Sinatra Biopic

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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.

Related Martin Scorsese’s New Movie Is A Big First For Leonardo DiCaprio - And A Major Challenge DiCaprio & Scorsese will team up for their seventh feature collaboration on a long-awaited Frank Sinatra biopic, which already poses a major concern.

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

In 1937, Sinatra was caught sleeping with a married woman, and he was arrested and charged with seduction and adultery.

Martin Scorsese's Frank Sinatra biopic will star Jennifer Lawrence alongside Leonardo DiCaprio as Ava Gardner, Sinatra's second wife. Sinatra was married four times in total, but his extramarital affairs were an open secret. Gossip columnists would frequently run articles about his love life, and they linked the singer to a long list of famous women. Some of his rumored partners included Lauren Bacall, Marilyn Monroe and other Hollywood stars.

Sinatra's womanizing ways even got him in trouble with the law once. In 1937, Sinatra was caught sleeping with a married woman, and he was arrested and charged with seduction and adultery, two serious crimes at the time. His marriage to actor Ava Gardner began in 1951, but he hadn't kicked his playboy lifestyle, and his widely publicized affairs were a major factor in the breakdown of their marriage.

7 Frank Sinatra's Son Was Once Kidnapped

The kidnapping plot changed Sinatra for good

Sinatra offered $1 million for the safe return of his son, even though the kidnappers only asked for $240,000.

While Frank Sinatra was still mourning the death of JFK, things almost got much worse for him. His son, Frank Jr, was kidnapped from his hotel room in Lake Tahoe at the age of 19. Fortunately, Frank Sr. was able to pay the ransom and his son was returned unharmed. The three perpetrators of the kidnapping were eventually caught and imprisoned, but the ordeal left a mark on Sinatra.

Sinatra offered $1 million for the safe return of his son, even though the kidnappers only asked for $240,000. For whatever reason, they declined his offer. Since the kidnappers insisted on communicating exclusively via payphone, Sinatra grew anxious that he wouldn't have enough change, so he started carrying a roll of dimes with him wherever he went. He kept this habit until the day he died, and he was even buried with ten dimes in his pocket.

6 Frank Sinatra Appeared In An Adult Movie When He Was A Teenager

Sinatra's glamorous movie career had an unexpected start

Sinatra earned $100 for starring in The Masked Bandit, according to one of his biographers, but the movie was never released.

Frank Sinatra began his career as a musician during his teenage years, but he had to resort to odd jobs to make ends meet before he hit the big time. He worked as a delivery boy for a newspaper and a riveter at a shipyard, but his wildest gig was as an adult movie star. Sinatra earned $100 for starring in The Masked Bandit, according to one of his biographers, but the movie was never released. Frank Sinatra's movie career took off much later, after he was already a well-known musician.

As the story goes, Sinatra regretted the adult movie almost immediately, so he called his friends in the mob to make sure that nobody ever saw the movie. He remained worried that the movie would eventually surface and damage his reputation throughout his career. Sammy Davis Jr. was the only person who knew Sinatra's secret, but he agreed to destroy his copy of the tape upon Sinatra's request. This story has never been officially confirmed, and any tapes are probably lost forever by now, if they ever really existed.

5 Frank Sinatra Once Raided An Apartment With Joe DiMaggio

Scorsese could retell the "wrong door raid" for laughs

Sinatra was a good friend to DiMaggio while the baseball star's marriage to Marilyn Monroe was falling apart

Frank Sinatra had many famous friends in his life, including legendary New York Yankee Joe DiMaggio. Sinatra was a good friend to DiMaggio while the baseball star's marriage to Marilyn Monroe was falling apart. One night when Sinatra and DiMaggio were drinking together, a private investigator called to say that Monroe had been spotted entering an apartment building, presumably to meet another man.

Sinatra and DiMaggio rushed off to confront Monroe and her new lover, but they kicked down the wrong door when they arrived. Florence Kotz got quite the shock when Frank Sinatra and Joe DiMaggio burst into her apartment in the middle of the night, and she later sued them successfully. Sinatra and Monroe would go on to develop a close relationship many years later, and she spent time at his casino on Lake Tahoe.

4 Frank Sinatra's Bet With Bruce Lee

Many Sinatra stories are hard to verify

Sinatra took an interest in martial arts after filming a fight scene for The Manchurian Candidate, so he started getting close to Bruce Lee.

There are many celebrity stories that nobody can verify, and Frank Sinatra's bet with Bruce Lee has gone down as a Hollywood legend, whether it actually happened or not. The story goes that Sinatra took an interest in martial arts after filming a fight scene for The Manchurian Candidate, so he started getting close to Bruce Lee, who was moving in Hollywood circles even though he wasn't yet a movie star. Sinatra bet Lee that he wouldn't be able to take a cigarette out the mouth of one of his bodyguards, but Lee proved him wrong with a flying kick that knocked the cigarette loose without hurting the man.

There are different versions of this story, with some accounts suggesting that Lee performed the stunt for a different singer, Vic Damone, rather than Sinatra. Martin Scorsese should still consider including it in his biopic. Even if the tale is fabricated, what it says about Sinatra's life is true. He regularly rubbed shoulders with the rich and famous, and he is part of more showbiz stories than most.

3 Frank Sinatra Tried To Stop The Production Of The Godfather

Sinatra was not a fan of Mario Puzo's novel

Sinatra went back and forth between wanting the movie canceled and wanting to play the part of Don Corleone himself.

If Frank Sinatra had gotten his way, one of the greatest movies of all time would never have been produced. Mario Puzo's best-selling novel The Godfather was a popular read among gangsters, although the book's portrayal of Italian-Americans was divisive. One man who was not impressed was Frank Sinatra, who objected to the character of Johnny Fontaine, a lounge singer based on himself.

Sinatra didn't like the way that The Godfather depicted him, but since Puzo's character had a different name, there was nothing he could do about it. Sinatra tried to stop The Godfather's production, fearing that a movie adaptation would only introduce Johnny Fontaine to a wider audience. Sinatra went back and forth between wanting the movie canceled and wanting to play the part of Don Corleone himself. He was unsuccessful either way.

2 Frank Sinatra Had A Violent Streak

Sinatra was well known for his bust-ups

There are stories from bars and clubs all over America about how Sinatra mistreated waiters and got in altercations with journalists.

Throughout his life, Frank Sinatra was notorious for his brash, aggressive ways, especially when he had been drinking. There are stories from bars and clubs all over America about how Sinatra mistreated waiters and got in altercations with journalists. However, Sinatra also showed his violent side when he was completely sober sometimes, even concocting premeditated attacks on people he disliked.

Sinatra's marriage with his third wife Mia Farrow didn't last long at all, but the two remained friends after their divorce. Years later, Farrow was publicly humiliated when her new partner Woody Allen left her for her adopted daughter Soon-Yi Previn. Sinatra sought Farrow's permission to hire a man to break Allen's legs in retaliation, but Farrow rejected this violent plan. No biopic of Sinatra would feel complete without alluding to his penchant for intimidation.

1 Frank Sinatra's Feud With Australia's Trade Unions

One of Sinatra's strangest tales took place in the 1970s

He and his team considered calling Henry Kissinger to get a military helicopter to extract Sinatra from Australia, but he eventually ironed out the disagreement without such drastic measures.

Frank Sinatra always had a fiery relationship with reporters, and this caused a huge problem on one of his Australian tours. Sinatra had done enough to anger his Australian fans before. He had canceled a tour at the last minute in protest at his travel arrangements, and he had gone on another tour which excluded Melbourne, the country's second most populous city, out of spite. When he returned in the 1970s, his bodyguards beat up reporters, and he went on a verbal tirade against the press on stage.

Australia's biggest union of journalists demanded an apology, and several other unions decided to put Sinatra on a blacklist in solidarity. Sinatra was unable to perform at the venues he had booked, fuel his plane to fly away, or even get room service in his hotel. He and his team considered calling Henry Kissinger to get a military helicopter to extract Sinatra from Australia, but he eventually ironed out the disagreement without such drastic measures. While blacklisted, he sang at a 50-seater venue in Sydney, the only one that would host him.