2. Holly Madison
The former Playboy girlfriend of Hugh Hefner had her DD assets insured for $1 million. Madison explained to People magazine saying, “If anything happened to my boobs, I’d be out for a few months and I’d probably be out a million dollars, I thought I’d cover my assets…they’re my primary money makers right now.” Last year, Holly opened her own speakeasy called 1923 Bourbon and Burlesque located at the Mandalay Bay hotel in Las Vegas.
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