Kim and Ray J – Ah, here we are. The relationship/sex tape that started it all and made the Kardashians household names for better or worse. In February of 2007, Kim’s sex tape with Brandy’s little brother leaked to the public for the viewing pleasure of men of all ages. The tape included intimate moments between the young couple making out and being cute by the pool to full-on humping. Vivid Entertainment bought the rights for the video with a price tag of $1 million and released Kim Kardashian: Superstar in late February. Kim immediately sued the adult entertainment company for the property of the tape but eventually settled to the tune of $5 million. A Kardashian making money for literally whoring themselves out to the public? Won’t be the last time we hear of something like that. Oh yea, Kim and Ray J broke up at some point too.