The Hollywood Gossip Caption Contest 52

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    Welcome, celebrity news fans around the world, to The Hollywood Gossip Caption Contest, our Friday tradition. Who won this week's Caption Contest?

    The winner is Katy Lynn. Congratulations! The winning entry appears below. Thanks to all of you for playing and best of luck again in this week's contest!

    Hugh and His Women

    Oh no! I have a hole in my right boob!


    I must, I must, I must increase my bust!


    holly madison...can she fit those in her mouth?


    HOLLY MADISON...loving those big balls


    Oh no! I have a hole in my right boob!


    Now that I'm single I think I want them to be this big!


    If the shaft is proportionate to the balls, Holly is gonna have to open up much wider.


    Holly Madison gets ready to bowl.

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    Holly Madison Biography

    Holly Madison Photograph
    Holly Madison is a Playboy model and the ex-girlfriend of Hugh Hefner. As for Madison, she is best known for getting naked a lot and... More »
    Astoria, Oregon
    Full Name
    Holly Cullen

    Holly Madison Quotes

    We are no closer to getting married than we were years ago. It's like a car stalled at the side of the road.

    Holly Madison [on Hugh Hefner]

    I have no pull anymore. Hef and I aren't together.

    Holly Madison