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Frank Sinatra was a true icon of the entertainment industry and one of the most successful singers of the 20th century. But out of the spotlight, the man dubbed Ol’ Blue Eyes had a rather colorful private life. And thanks to the star’s apparent associations with dangerous organized crime figures, a long shadow has been cast over his legacy. So, is there any truth to the shocking rumors that dogged Sinatra even before his death?

Image: Ron Galella, Ltd./Ron Galella Collection via Getty Images

Indeed, some of the gossip surrounding the singer stands in marked contrast to the enduring vision of him as a slick, expensive-suit-wearing crooner. And Sinatra’s music was arguably the soundtrack to an era. In his 1940s and 1950s heyday, he released countless hit singles and chart-topping albums as well as scooping an Academy Award.

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