Miss America MILF: Vanessa Williams

Age: 45
# of kids: 4
Beauty queens look good, but they’re usually too stuck up to let loose. That’s why this triple threat (model, singer, actress) still has the crown in our minds. On one hand, she’s evolved into a graceful woman who cleans up at the NAACP Image Awards (above). On the other hand, she was pictured in Penthouse with another woman going down on her. If that ain’t the best of both worlds, we don’t know what is.

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