Jennifer Aniston | Actress | $300 Million

With $300 million in net worth, we know Jennifer Aniston as one of the most versatile and talented actresses in Hollywood these days. She has certainly earned her fame and her millions, but did you know that before she achieved these things, Jen was actually a struggling actress? Fortunately for her, after a series of failed auditions, she chanced upon TV executive Warren Littlefield at a gas station!

There, she asked the exec for advice on what to do next. He encouraged as well as helped the actress get cast in F.R.I.E.N.D.S. The show turned out to be massively successful, leading to bigger projects for Jennifer. Since then, and for two decades already, she gets to win every lead role she can get and even the accolades and achievements that go with it. Annually, she can easily earn a paycheck of over $20 million from acting stints and her endorsements.