2) Ray J (2004)
Kim should probably thank Ray J more than any one of her previous exes for putting her on the entertainment map. That’s because a homemade sex tape that the two made surfaced in 2007 – well after the two had called it quits, but significant enough to take the tabloids by storm and put her front and center. Kim met Ray J after she became the personal assistant to his sister, Brandy, in 2004. For the record, Kim made out OK from her time with Ray J – not only did the sex tape help launch her career into super stardom, but she also won a lawsuit against Vivid Entertainment to stop its distribution.