Iconic Frank Sinatra’s Playboy Lifestyle Exposed In Tell-All Interviews

Iconic Fly Me To The Moon singer Frank Sinatra led a glitzy playboy life once his immense talent was picked up by Hollywood, Host and Bestselling Author Kitty Kelley reveals in her latest episode of The Kitty Kelley Files.

“This young singer that was having young girls line up around the block was soon noticed by Hollywood,” says Kelley in the clip.

After spending his teenage days working as a singing waiter in Hoboken, New Jersey, Sinatra soon was discovered by a small agency with whom he appeared in light musicals.

“A few years later he came to the notice of MGM,” adds Kelley. “He appeared in Anchors Aweigh, and they signed him to a contract for $1.5 million dollars in 1945.”

Making massive amounts of money – especially for the era he lived in – Sinatra quickly got involved in the whirlwind that was 20th century Hollywood.

“When he made the move out to Hollywood, Sinatra was immediately infatuated with some of the most beautiful movie stars of the day,” says Historian and Author Barry Bradford.

“He was in trance with Marilyn Maxwell,” adds Kelly in the clip, when speaking of Sinatra’s infatuation with the 1940s sex symbol.

“He had a very torrid relationship with Lana Turner and then after that Marlene Dietrich comes along, who was much older than Frank,” adds Bradford.

His first wife, Nancy Barbato, “quickly became aware of the fact that Frank was stepping out on her,” says Bradford.

Sure enough, he met stunning singer/actress Ava Gardner and divorced his wife of 12 years in 1951. That same year, he married Gardner.

The handsome music icon went on to have two more wives after he divorced her six years later.

The Kitty Kelley Files: Frank Sinatra airs Saturday, August 5 at 10 ET/PT.