Winona Ryder, 46 – ~ $18 Million
Back in the ‘80s, Winona Ryder isn’t just a prominent actress, she was also an inspiration to some teenage girls. It all started with her cult classic films such as Girl, Interrupted, Reality Bites, Beetle Juice, and Heathers. Winona remained active until 2000, appearing in films such as Boys, Alien Resurrection, and Autumn in New York. However, in 2001, she took a break from acting after being arrested for shoplifting, but she was able to appear in two films before her arrest. Fortunately, she was still able to regain her career and has appeared again in the popular Netflix series, Stranger Things.