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Four Times Don Rickles Roasted Powerful People Right To Their Faces

youtube screenshot: https://www.youtube.com/watch?v=q5_V9RT8aR8

Don Rickles was fearless. He didn’t care who you were or where he was, if there was a joke to be made, Rickles would do it. Mr. Warmth is known as one of the greatest comics ever. He’s an innovator who basically invented insult comedy and perfected the art of roasting.

Rickles was fearless and would say the meanest things right to your face, and you would keel over in laughter. Rickles spoke humor to power quite a few times. Here are a few of our favorite examples.

When He Tore Up GOVERNOR Ronald Reagan And Others At A Roast

One of Rickles’ biggest targets was Ronald Reagan. Spanning several decades, Rickles never missed an opportunity to roast The Gipper. At one of the Dean Martin Roasts, Rickles skewered the future governor of California so hard that Reagan, Sinatra, and others almost fell out of their chairs.

Roasted President Reagan At His Own Inauguration

He didn’t stop when Reagan was President. Rickles went after the President, his cabinet, and nearly everyone else in attendance at the President’s second inauguration in 1985.

Rickles Vs. Sinatra

Frank Sinatra was infamous for his standoffish attitude and cold demeanor when he wasn’t on stage. Rickles didn’t care. Don was one of the few men who could take a shot at Sinatra.

Rickles once asked Sinatra to come to say hello when Rickles was on a date. Naturally, Don wanted to impress the girl with the fact that he knew Sinatra. But it was a trap. Sinatra approached Rickles and his date, and Rickles snubbed The Chairman right to his face.

Donald Rickles Makes Clint Eastwood’s Day

Don Rickles and Clint Eastwood on the set of Kelly’s Heroes… pic.twitter.com/NS2tXNkZQq

— Classic Movie Hub (@ClassicMovieHub) May 9, 2022

I don’t care how old he is, I would never dare insult Clint Eastwood. Not even on the Internet, much less to his face. Rickles of course had no fear.

Bonus: Rickles Busts DeNiro On The Set Of Casino

Even on the set of a very serious movie, Rickles wasn’t afraid to cut up between takes. Here he takes on Robert DeNiro to break up the tension during a tough scene in Casino.

Legendary comedian DON RICKLES was born on this day in 1926. Here he is busting De Niro’s chops on the set of CASINO (1995). pic.twitter.com/4P76WUZqTu

— All The Right Movies (@ATRightMovies) May 8, 2022

And don’t think Rickles couldn’t be funny on paper, either.

My favorite find in De Niro’s Papers is this letter from Don Rickles:

Dear Bob
Just a note to let you know how much we appreciate your thoughfulness with the great bottle of Chateau Lafite Rothchild. We put it in a brown bag and boozed it up with the winos on Hollywood Avenue.

— R Colin Tait ?? (@rcolintait) May 12, 2022

Are you a fan of Don Rickles? Share your thoughts in the comments below.

Want more Rickles roasts? Check out Dean Martin Was Left In Tears When Don Rickles Roasted Bob Hope.

Hunter Patterson

Hunter Patterson is a writer based in Los Angeles. He loves writing about pop culture, popcorn, and pro wrestling. When he isn't writing, he is working on several creative endeavors. In his free time, he enjoys reading science fiction, perfecting his chili recipe, and exploring Los Angeles' amazing culinary scene.