Lisa Marie Presley
Lisa Marie is the daughter of an incredibly famous rockstar whose last name was Presley. She grew up extraordinarily wealthy. Before Elvis passed away, he made sure that Lisa had everything she could have ever wanted. But, even after he left $100 million to her in his will, she blew through that and ended up selling his estate for more spending money. She went through an extremely pricy divorce that left her $16 million in debt, a number that she hasn't been able to recover from since then.