16. Jessica Simpson
Net worth: 200 million dollars* Year to retire: 2014.
Where are they now:Founders of Warm Up clothing
Jessica Simpson’s music and acting careers span 20 years. Jessica Simpson was 17 when she first came into the spotlight. She has been categorized as a “ditzy brunette”. She starred as Daisy Duke’s face for many years. This partnership brought her both blessings, and curses. Her image was perfect for the Daisy Duke brand.

Simpson hasn’t acted since 2014, and she has focused on her fashion line and philanthropy ever since. Jessica Simpson Collection is her clothing line, and it has generated over $1 billion dollars in revenue.