A Broke Frank Sinatra Starred in a Pornographic Film, Claims Biographer

Frank Sinatra’s career exploded in the 1940s and, though there were several bumps in the road, he remained famous until he died in 1998. According to one biographer, Sinatra’s early artistic pursuits were not very lucrative. The biographer alleges that to make ends meet, Sinatra appeared in a pornographic film. Apparently, Sinatra was furious when his friends discovered the film several decades later.

Frank Sinatra wears a suit and sits in an orange chair with a cigarette.
Frank Sinatra | Silver Screen Collection/Getty Images

Frank Sinatra decided he wanted to be a singer at a young age

Sinatra was born in Hoboken, New Jersey, and knew he wanted to become a singer when he heard Bing Crosby’s recordings. He believed that his own voice was skilled enough to lift him to success. From a young age, he performed at his parent’s bar. According to Rolling Stone, his mother didn’t initially want him to be a singer. When he continued pushing for this career, however, she used her considerable influence to help him.

She convinced a local singing trio to let her son join, and, in 1935, the group found success on a radio show. In 1939, Sinatra left the singing group and began performing with trombonist Tommy Dorsey’s big band. By 1943, he was a star by his own right, commanding screaming audiences across the country.

He reportedly agreed to appear in a pornographic film to make money

Before all this success, however, Sinatra was a struggling artist. According to one biographer, the lean years of Sinatra’s career led him to appear in a 1934 pornographic film. Writer Darwin Porter has penned multiple celebrity biographies and spent years researching for his book Frank Sinatra, the Boudoir Singer: All the Gossip Unfit to Print from the Glory Days of Ol’ Blue Eyes. Porter claims he learned about the film, The Masked Bandit, from Peter Lawford, a member of the Rat Pack.

According to Davis, Sinatra received $100 for his role in the film and hoped it would remain a secret for the rest of his career. Ultimately, though, his friends discovered the film. Sammy Davis Jr., another Rat Pack member, reportedly had a collection of pornography that included The Masked Bandit. At a party in 1972, Davis claims that Sinatra’s friends inserted footage from the film onto another reel. Though the character’s mask prevented any other guests from knowing it was a young Sinatra on screen, the “My Way” singer was reportedly furious. He made Davis Jr. destroy his copy of the film.

Davis alleges that many stars of the era appeared in pornographic films to make money.

“Years later, a segment of The Masked Bandit was considered for insertion in a film about stars such as Joan Crawford who had appeared in porn before they became famous,” Davis told The Daily Mail. “When Frank heard about this, he called his friends in the mob. The bandit loop never resurfaced.”

Another Sinatra biographer, James Kaplan, agreed that Sinatra was struggling in the early 1930s. He could not confirm that he appeared in The Masked Bandit, however. Kaplan wondered if Lawford invented the story because the two had a falling out in the 1960s.

Frank Sinatra was not a fan of tell-all biographies 

Though Davis’ book came out over 10 years after Sinatra’s death, the crooner likely would have disapproved of the biography. In 1988, Sinatra told Larry King that he couldn’t stand “kiss-and-tell” books. Per AP, Sinatra told King that the authors of tell-all biographies ″can’t write their own name to earn a living properly.″

“They’ve got to lean on somebody else, and they know nothing about the person of whom they’ve written,″ he said.

Still, he said that he’d been through enough in his life that a disparaging anecdote in a book wouldn’t bother him.

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