Kim Kardashian and Ray J
In 2007, a pornographic home tape of Ray and his then-girlfriend, Kim Kardashian, from four years prior was released by Vivid Entertainment. Though Kim sued the company and later settled for $5 million, many argue that the sex tape turned Kim into an overnight superstar. Recent reports have claimed that Kim’s mother, Kris Jenner, may have brokered the deal for her porno.