Don Rickles Roasted Clint Eastwood, No One Could Keep A Straight Face

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When it came to roasting celebrities, no one did it better than Don Rickles. In a television classic, the brash comedian took on Clint Eastwood, and no one could keep a straight face.

Clint Eastwood and Dina Eastwood laugh as Don Rickles roasted the legendary actor (Credit: YouTube)

Many moviegoers think of Clint Eastwood as a rough and tumble cowboy. Over the years, he’s played in several classic western films. He even got his start in the western TV show Rawhide. However, Eastwood never limited himself when it came to roles. In his career, he has portrayed men from just about every walk of life. In 1970, the world saw him as a WWII soldier in the adventure-comedy film Kelly’s Heroes.

Kelly’s Heroes had a killer cast. Clint Eastwood, of course, played the lead. Additionally, the cast featured Donald Sutherland, Carroll O’Connor, Gavin MacLeod, Harry Dean Stanton, and Don Rickles. In the film, Rickles and Eastwood went together like peanut butter and jelly.

Don Rickles
Don Rickles roasts Clint Eastwood (Credit: YouTube)

However, the pairing of Clint Eastwood and Don Rickles also proves that opposites attract. At the very least, it proves that opposites work well together. Even in the late sixties, everyone saw Eastwood as the strong silent type. On the other hand, most people knew Rickles for his comedic chops.

More specifically, Rickles was an insult comic and one of the best to ever do it. So, if anyone was going to roast Eastwood, it was going to be Rickles. He got more laughs in a couple of minutes than most comedians get in a half-hour. Eastwood took it like a champ, laughing along with the crowd at his own expense.

Rickles roasted Eastwood another time on the set of Kelly’s Heroes. You could tell that the two-minute clip was going to be comedy gold within the first few seconds as Rickles set up his roast of Eastwood with the opening line, “Clint, we’ve been on the picture with you for about two days. I just want to say, on behalf of the whole cast, Clint, we’re fed up.”

This broke Eastwood’s usual stone-faced demeanor. The Hollywood legend let out a laugh at Rickles’ opening volley, and the laughs kept coming as the comic continued his roast. However, he didn’t keep his comedic sights on Eastwood. Rickles fired some shots at Kelly’s Heroes as a whole.

Don Rickles
Clint Eastwood and Don Rickles starred in Kelly’s Heroes (Credit: YouTube)

“Seriously speaking,” Don Rickles began, looking at Clint Eastwood. “Basically, I’ve read the script and you’ve read the script. Now that we’ve both read it, let’s get on a plane and go home. Because I think it’s bad!” This got an even bigger laugh from Eastwood and the other members of the cast and crew standing just out of frame.

Then, Rickles turned his jokes toward Eastwood again. He asked him how long he’s been in motion pictures. Slow to speak, Eastwood took a couple of seconds to respond with “about 16 years.” However, that couple of seconds of silence was all the veteran comic needed to come up with more jokes. “Clint got off a ripper there, folks. We’ve been going through it for three or four days with these little rippers.” The best part about the video is watching Eastwood double over with laughter as Rickles works his comedic magic.

Another major Hollywood star whom Don Rickles roasted became president of the United States. At the time, Ronald Reagan was in his seventh year as governor of California. Dean Martin hosted a celebrity roast and invited the Governor to be the subject. But, because he had been an actor, there was a lot more to talk about than a typical governor.

According to Rickles, it was the first time he had ever met the then-governor. So, the nerves must have been running high for him as he was letting the jokes fly. No matter, though, as Reagan absolutely loved the showing and was dying laughing at almost all of the jokes Rickles had for him. It certainly goes to show how incredible Reagan’s humor was. Additionally, for those who remember, Rickles was one of the best roast comics of his era.