Tippi Hedren, 88 – $20 million
Former fashion model, actress, and activist Tippi Hedren got discovered by Alfred Hitchcock in 1961 and she would go on to star in his movies like The Birds and Marnie. Tippi has appeared in more than 80 movies and TV shows and received a star on the Hollywood Walk of Fame. Hedren worked eleven years on the film Roar and later founded the Roar Foundation to protect wildlife. Due to severe headaches, Tippi has been unable to work. When she finally felt better and accepted a role on Fashion House, she was hurt and the headaches returned. She later sued her lawyer but never collected the money from the settlement.