The “Boob Job Contest”

Once in a blue moon, Howard manages to surprise us even more than usual. In 2000, the radio host tried talking Erica the Gymnast, the winner of the “Boob Job Contest,” out of claiming her prize. While he begged and pleaded with her not to go through with the surgery—claiming he liked her girl-next-door charm—in the end, he couldn’t sway her decision, and helped fund the procedure. His only condition? Don’t go too big.