Liza Minnelli and David Gest
Poor Liza doesn't have the greatest track record with men. The star's first marriage, to Aussie entertainer Peter Allen, lasted for seven years, from 1967 to 1974, but the Boy from Oz performer became a gay icon in the years following their marriage. Her fourth marriage, to concert promoter David Gest, was arguably one of the biggest train wrecks in Hollywood history. After their high-profile nuptials—where Michael Jackson was the best man and Liz Taylor was the maid of honor—their marriage fell apart after 16 months. Gest later made a public spectacle of their relationship by suing Minnelli, claiming she was an alcoholic and abused him, but the suit was dismissed because of a lack of evidence. Since their marriage, Gest has repeatedly denied he was gay. And apparently, the apple doesn't fall from the tree. Minnelli's mother, Judy Garland, also had questionable taste—two of her husbands, film director Vincente Minnelli and disco manager Mickey Deans, were also believed to be gay.