ADAM SANDLER — EST. $420 MILLION

Adam Sandler needs no introduction. From the 1990s until today, this powerhouse comedian still wows everyone with his superb acting and comical acts. Sandler rose to prominence as a member of the comedy skit show Saturday Night Live which is amazing considering very few of the films he’s been involved with can be considered box office hits. Sandler is among the highest-earning stars, accumulating $2 billion at the box office. In 2002, he starred in Wild Love and was nominated for Best Actor in a Comedy Series at the 60th Golden Globe Awards.

But one of the reasons why Sandler has so much money is because he created his own production company, Happy Madison, which was involved in the production of most of his films. Indeed, Happy Madison has been producing films and raking in millions of dollars every year since it was founded in 1999. Sandler is reportedly worth $420 million now. Today, he holds three Golden Raspberry Awards and 11 Raspberry Award nominations, a feat he matches Sylvester Stallone with.