Adam Sandler | $420 Million

No other actor could hold a crowd’s attention like Adam Sandler. He’s demonstrated repeatedly that his films can still generate millions at the box office. Some would argue that there’s something magical going on there. However, in reality, Sandler’s singular approach to comedy—and acting in general—has propelled him to an impenetrable apex that only he can reach.It is where fellow comedian Dennis Miller spotted his talent for comedy.

Sandler has amassed investment money in his career, but not all have come from comedy. His $420 million net worth results from many film and music industries projects. He began his illustrious career on The Cosby Show as Smitty. Shortly before entering the comedy club scene, he starred in his debut film, Going Overboard, in 1989.  He recommended Sandler for a Saturday Night Live audition, and the rest was history for Sandler from that moment on.