Kim Kardashian
In 2007, Kim Kardashian posed for the men’s mag in a series of sexy shots with her mother Kris Jenner’s blessing. Unfortunately for Kim, however, she now regrets the racy nude photos.
“I’m sorry I did Playboy. I was uncomfortable,” Kim said. “Go for it,” she recalls her mother saying. “They might never ask you again. Our show isn’t on the air yet. No one knows who you are. Do it and you’ll have these beautiful pictures to look at when you’re my age.”