On September 29 at the age of 85, screen legend Tony Curtis died of a heart attack, leaving behind a wife, five children (including actress Jamie Lee Curtis) and millions of saddened fans. 10 Old Hollywood Hotties We Miss
He also leaves behind quite a sexual legacy. Best known onscreen for wearing a skirt in Some Like it Hot, Tony was equally famous offscreen for chasing skirts. It's been reported that the devilishly handsome actor—who once lived at the Playboy Mansion—bedded 1,000 women, including actresses Natalie Wood and Marilyn Monroe.
Tony first met Marilyn in 1949, when she was still an unknown. The two began a passionate relationship, which was ultimately derailed by their showbiz ambitions. In his memoir, American Prince, Tony says, "I loved her. And she loved me, but we both wanted to be in the movies, and that meant everything."
In 1950, Tony began romancing Psycho actress Janet Leigh, whom he married the following year. The two quickly became Hollywood's "it" couple, appearing together in movies like Houdini. Although they seemed the perfect pair, Tony was perpetually unfaithful to his wife. One of his many affairs was with former flame Marilyn Monroe, with whom he was reunited in 1958 on the set of Some Like It Hot. In his behind-the-scenes tell-all, Tony claimed that Marilyn, then married to playwright Arthur Miller, became pregnant with his child. Their affair ended when the film wrapped, and Marilyn later suffered a miscarriage.
In 1962, after 11 years of marriage and two daughters, Tony divorced Janet to marry 17-year-old Christine Kaufmann, his co-star in Taras Bulba. Tony's second union—which only lasted about four years—also produced two daughters.
The marriage to Christine was barely over before Tony wed again in 1968, to model Leslie Allen, who gave him two sons (one of whom, Nicholas, sadly died of a drug overdose in 1994). Although this third marriage was his longest, it wasn't "the charm," and ended after 14 years.