The Many Loves Of Hugh Hefner, The Luckiest Bastard In The World

Holly Madison
Hef's main squeeze during The Girls Next Door heyday, Holly seemed genuinely in love with Hugh, who unfortunately was not the marrying kind. Lucky for her, she went on to date Cris Angel. Which we guess is trading sideways? Holly also appeared on Dancing with the Stars in 2009, and is starring this summer in her reality show Holly's World on E! Who said dreams never come true? Oh, you know, those dreams where you aren't pinned under an old man. Those dreams. [Photo: Getty Images]