9. SYLVESTER STALLONE – $400 MILLION
Sylvester Stallone is a very rich man who took a very big gamble. He was hard on his luck (he even had to sell his dog) when he started shopping the script for Rocky. As soon as he sold the script, he bought his dog back (for much more than he sold him for). After that, he created two of the most successful movie franchises in history with Rocky and Rambo.