Bruce Willis | $300 Million | Businessman

Actor Bruce Willis has graced the screens with his talents and good looks, but he is also quite the businessman behind the camera. He has engaged in several business ventures in the past, including a production company, food and beverage, and endorsement deals that asked for company shares. His financial advisers are probably very proud of him for making these steps.

In 2000, he started Cheyenne Enterprises, a motion picture production company that he put up with Arnold Rifkin. However, he left the company and left it with Arnold in 2007. He also owns a bar called The Mint Bar in Hailey, Idaho, which he eventually gave up on as well. Beside the bar was The Liberty Theater, which was also his. On top of this, he is one of the restaurants Planet Hollywood co-founders, along with Arnold Schwarzenegger and Sylvester Stallone.  Finally, he signed an endorsement contract with Sobieski Vodka in 2009 that required 3.3% ownership of the company as compensation.