Jackie Mason wasn't afraid to push the boundaries of humor, even at the expense of his popularity. Once a regular on "The Ed Sullivan Show," Mason was kicked off the program for two years after making a finger gesture that Sullivan misinterpreted as obscene. A wisecrack he made about Frank Sinatra got him beaten up by a mysterious attacker (via The Washington Post). No target was too big for Mason — not even the leader of the free world. In 2011, the comedian gave a radio interview in which he berated then-president Barack Obama for holding a White House Hanukkah celebration nearly two weeks before the actual Jewish holiday. "He doesn't know, he doesn't care," Mason declared (via The Hollywood Reporter). "He's strictly in there to take a picture, and the picture could have been about anything."
Indeed, the comedian often raised eyebrows for his political views. In addition to his criticism of Obama and other prominent Democrats, The Hollywood Reporter also noted in 2015 that Mason called then-presidential-hopeful Donald Trump "a colorful, dynamic character" who shouldn't be underestimated.
Mason's controversial comments didn't hurt his bank account, however. At the time of his death, the legendary funnyman was worth a comfortable $9 million, per Celebrity Net Worth. There has been no word on who will inherit his estate; however, he is survived by his wife Jyll Rosenfeld and a daughter by a previous relationship.
