Will Smith | $350 million

Aladdin actor Will Smith is dubbed the most powerful actor in Hollywood, and we can confidently say he is worthy of that particular title. Why? Out of the 21 films where he had leading roles as of 2014, 17of which grossed over $100 million each. Put his name on the cast list, and for sure that movie is going to sell out. Of course, his skills had been honed by being active in the industry since 1986. He has also worked in a number of films that tested his acting skills, such as Ali and The Pursuit of Happyness.

While Smith is a risk-taker, he makes sure that all of them are calculated risks. All of the financial ventures are coursed through his venture capital fund, Dreamers VC. Most likely, all his decisions are run through his financial advisor and business partners first. By being selective about where he puts his money, Smith was able to grow his money. Among those he took risks on are Nurx and Genome Medical.