6. Dating Hugh Hefner

This is mean … but it's true. Holly Madison. Kendra Wilkinson. Bridget Marquardt. I bet a lot of you find these names at least a little familiar, right? But I also bet you wouldn't know them from Adam if these three women hadn't “dated” Hugh Hefner. And gotten their own show because of that. And then gotten spin-offs of those shows. And what about Crystal Harris? Famous, actually, for dumping Hugh Hefner – she's totally one of a kind!