15 Celebs Still Pretending To Be RICH. Most of us are used to being inspired by rags to riches stories, where someone starts from nothing and works their way up to great wealth. Well, today, we are going to go in the opposite direction and show you some riches to rags story about people who had it all and then lost it. Although these stars might try to keep up appearances by showing off on social media, behind the scenes they are in a lot of financial trouble. Kanye West has always talked a huge game, but putting aside his profitable music career to explore the volatile world of fashion proved to be a huge mistake. Bow Wow talks a big game on social media, but has been busted several times faking his wealth. Some celebrities such as DMX and Tori Spelling are so deeply in debt and owe so much money in back taxes that they could potentially end up in jail as a result. Even some big name, classic actors struggle with their mounting debts due to their extravagant lifestyles. It seems that stars Johnny Depp, Nicholas Cage, and Brendan Fraser have been spending their money much faster than they can make it. Some stars, like Alyssa Milano and Aaron Carter, claim that their financial woes are a result of trusting the wrong people to manage their finances, and not due to their own mistakes. Drake Bell has been working since he was a child, so it’s shocking that he has managed to amass and lose such a great fortune.