It was 1974. The air in the room was thick with cigarette smoke and the kind of high-octane ego you only find when the Rat Pack is in town. Dean Martin, looking as relaxed as a man who’d just finished his third martini, leaned into the microphone. He wasn’t there to praise the man sitting next to him. No, he was there to light the fuse on the roast of don rickles, an event that remains a masterclass in how to offend everyone while making them love you for it.
Rickles sat there, grinning like a shark that had just spotted a slow-moving tuna. They called him "Mr. Warmth," a nickname so sarcastic it practically dripped off the screen.
The Night the Merchant of Venom Got Stung
Most people think of roasts as those mean-spirited Comedy Central specials where C-list celebrities trade barbs about plastic surgery. But the 1974 Dean Martin Celebrity Roast of Don Rickles was different. It was a heavyweight bout. You had Bob Newhart, Casey Kasem, and even Phyllis Diller lined up to take shots at a man whose entire career was built on calling people "dummies" and "hockey pucks."
Newhart, Rickles' best friend in real life, delivered a set that was pure surgical precision. He didn't scream. He didn't need to. He just used that stuttering, deadpan timing to suggest that Rickles was actually a deeply sensitive man who cried at the sight of a wilted flower. The contrast was hilarious. Rickles, meanwhile, was physically vibrating in his chair, waiting for his turn to retaliate.
When Rickles finally took the podium, he didn't just respond; he scorched the earth. He went after Dean Martin’s drinking. He went after the audience. Honestly, he went after the concept of politeness itself. It wasn't just "insult comedy." It was a high-wire act where the net was made of razor wire.
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The 2014 Spike TV Tribute: One Night Only
Fast forward forty years. The venue moved from a smoky Las Vegas ballroom to the historic Apollo Theater in New York. The special was titled Don Rickles: One Night Only, and while it was billed as a tribute, it functioned as a secondary, more modern roast of don rickles.
Jerry Seinfeld hosted. Think about that for a second. The man who made a billion dollars talking about nothing was paying homage to the man who made a career out of saying everything you aren't supposed to say. The guest list was a fever dream of talent:
- Martin Scorsese and Robert De Niro: They sat there looking like they were at a mob summit while Rickles told them they were "boring."
- Tina Fey and Amy Poehler: They brought a sharp, modern wit that proved Rickles’ style wasn't just for the "old guard."
- David Letterman: Making a rare appearance outside his own show to honor the man who had appeared on his couch over 90 times.
The most incredible part of that night? Rickles was 88 years old. Most people at 88 are struggling to find their car keys, but Don was still sharp enough to cut glass. He stood up at the end and roasted the entire front row without a single cue card. He looked at Regis Philbin and told him he looked like he was "waiting for a bus to the home." It was brutal. It was perfect.
Why We Can't Stop Watching
Why does a roast of don rickles work when so many other roasts feel forced? It's the "hug" at the end. Rickles had this uncanny ability to make you feel like being insulted by him was an induction into an exclusive club. If he didn't call you a name, it meant he didn't care about you.
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Sinatra loved him. Reagan loved him.
He broke every rule of modern sensitivity, yet he rarely felt truly "mean." He attacked everyone equally—race, religion, weight, height—it didn't matter. In his world, we were all equally ridiculous. He turned the roast format into a mirror. By laughing at his "victims," we were really laughing at the absurdity of our own insecurities.
Lessons from the Master of the Roast
If you’re looking to understand why Rickles remains the gold standard for this format, you have to look at the structure of his attacks. He never punched down. Even when he was mocking a waiter or a guy in the third row, he did it from the perspective of a man who knew he was just as flawed as they were.
Basically, he taught us that if you're going to tell a joke that pushes the envelope, you better have the charisma to pull the audience back in before the envelope tears.
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- Timing is everything: Rickles never rushed the punchline. He let the silence do the heavy lifting.
- Know your audience: He knew exactly how far he could push Sinatra versus how far he could push a civilian.
- Self-deprecation: He was the first person to make fun of his own "bullet head" and his lack of a "real" acting career outside of bit parts.
Where to Find the Best Clips Today
You can’t just go to a comedy club and see this anymore. The era of the "all-star" roast is mostly dead, replaced by highly scripted, overly produced specials. But if you want the real deal, hunt down the 1974 footage. Look for the moments where the camera catches the other comedians laughing—not the polite "I'm on TV" laugh, but the "I can't believe he just said that" wheeze.
Check out the One Night Only special if you want to see the emotional side of comedy. Seeing Letterman and Seinfeld get misty-eyed over a man who called them "idiots" for thirty years is surprisingly moving.
Next Steps for Comedy Fans:
To truly appreciate the legacy of the roast of don rickles, watch his final appearance on The Tonight Show Starring Jimmy Fallon. Then, go back and watch his first appearance with Johnny Carson in 1965. Notice the consistency. He never changed his act to fit the times; the times eventually changed to realize he was right all along. Laughter is the only thing that actually levels the playing field.