Britney Spears (39) – $70 Million

In the early 2000s, Britney had a lot going for her. She was practically on top of the world, with a string of Grammy awards and world tours. In fact, she was named the world’s most powerful celebrity by Forbes in 2002, beating her contemporaries like J.Lo and Jessica Simpson, hands down.

Sadly, the pop star’s upward trajectory dropped when she experienced some mental struggles in 2008 and was placed under conservatorship, with the control of her finances handed over to her father, James. This arrangement hasn’t been favorable for her career, and now she has a net worth of $70 million.