Leonardo DiCaprio, Actor, $262 million

Leonardo DiCaprio has seen life on both sides. The famous actor, who is well known for his role in “The Wolf of Wall Street,” is worth a fortune but grew up as a very poor kid in an environment where drug use and violence were the order of the day.

His career wasn’t also smooth. He found it hard to get an agent who would take him and almost quit the acting dream when he was without work for nearly two years, despite having done over 100 auditions. He eventually had his shot at fame when he was cast in the 1997 movie “Titanic.”