Take a closer look at Frank Sinatra’s 4 Wives in Pictures: from Nancy Barbato to Barbara Marx in this comprehensive feature.

By the mid-1960s, Sinatra had reinvented himself as the swaggering godfather of the Rat Pack, ruling Las Vegas and the global music charts. Then, in 1964 on the 20th Century Fox lot, forty-eight-year-old Sinatra crossed paths with nineteen-year-old Mia Farrow, then starring in the television soap opera Peyton Place. The press went wild over the thirty-year age gap. Journalists ridiculed the pairing, framing Farrow as an ethereal pixie wandering into the den of an aging, hard-drinking lion.

They married in a private, fifteen-minute ceremony at the Sands Hotel in Las Vegas on July 19, 1966. Sinatra expected Farrow to step away from acting and assume the role of an attentive Palm Springs hostess, catering to his schedule and traveling with his circle. Farrow, eager to stretch her dramatic capabilities, resisted the domestic mold. When director Roman Polanski offered her the lead role in the psychological horror thriller Rosemary's Baby in 1967, she accepted the assignment against Sinatra's explicit wishes.

The production ran severely over schedule in New York City. Furious that his wife was unavailable to co-star alongside him in the detective drama The Detective, Sinatra took ruthless action. In November 1967, Sinatra’s attorney arrived unannounced on the Paramount soundstage where Farrow was filming and handed her divorce papers in front of the cast and crew. The legal split was finalized in August 1968 in Juarez, Mexico. Farrow later reflected that she was simply too immature to handle Sinatra’s complex demands, yet the pair remained warm confidants for the rest of his life.