3. Holly Madison
One of many Hugh Hefner’s former girlfriend, as well as a popular reality television superstar, Holly Madison has her breast insured at $1 million. And we can see why she did that, those balloons look like they are going to pop any second. She decided to insure her boobs in the time she was doing her Las Vegas show, also known as the “Peepshow”. Her breast insurance policy covers a wide range of possible things that can happen, such as plastic surgery mishaps, her silicon implants, as well as any possible physical and medical abnormalities that may happen while she runs her successful career.