Jackie Mason – 87

Jackie Mason is a famous American comedian who is known for his controversial jokes and his recognizable voice. He often uses his Jewish background for jokes and talks a lot about politics and race in his stand-up acts. His shows have amused Broadway audiences for decades as he has performed as a solo act six times, leading to a net worth of $9 million. Mason did get into some trouble with some of his jokes cutting a bit too close to the bone, but he never ceased to make his audiences laugh. After an alleged attack by a friend, he kept a probation attorney close just in case any legal problems would ever come up.