The Best of Don Rickles’s Hilariously Insulting Comedy Routines

Don Rickles, the acclaimed king of insult comedy, has died at the age of 90, and the world is a less funny place for his passing.

Rickles, the creator and star of both a variety show and a sitcom, as well as a blistering stand-up act, was known for his razor sharp wit, quick timing, and no-holds-barred approach to insult comedy. He had a knack for spotting insecurities and weakness, pouncing on them by laying on one hilarious insult after another.

In addition to his other work, Rickles became known throughout his comedy life — active well into his 80s — as the most proficient roaster of pretty much everyone. There was no one and nothing that he wasn’t willing to take on. He roasted celebrities and politicians, sometimes both at the same time, and he was irresistibly funny while he did it.

So, in memory of Don Rickles’s broad catalog and decades-long career, here are five of his most hilariously insulting roast routines. Fair warning, he doesn’t hold back.

5. Don Rickles Roasts Clint Eastwood

He is one of the best-loved and most acclaimed stars of American cinema in film history, but none of those accolades could keep Clint Eastwood safe from Rickles for ignoring his existence for the first 30 seconds of his bit.

4. Don Rickles Roasts Evel Knievel

“I really don’t like you, Evel. I never did,” says Rickles to kick off his roast of the iconic stunt performer. Suddenly all of his “motorcycle tricks” don’t seem so grand once the comedian gets ahold of them. That’s to say nothing of the way Rickles handles the presence of Barry Goldwater, the Republican party presidential nominee who ran on a platform of racial segregation.

3. Don Rickles Roasts Frank Sinatra

Rickles’s wild energy is front and center in his roast of one of the greatest American songwriters. No one is safe.

2. Don Rickles Roasts Lucille Ball

Lucille Ball is one of the funniest stars ever to grace American television screens. Didn’t stop Rickles from yelling “Put her in a home!” as she shrugs in answer to a question.

1. Don Rickles Roasts Ronald Reagan

It’s not a lot of people who say they’ve gotten the opportunity to roast a U.S. president. Rickles belongs to that select group. His roast of Ronald Reagan, back before the governor of California became president, feels like watching a piece of history.

Bonus Round: Tine Fey and Amy Poehler Roast Don Rickles

A tribute to this insult comic wouldn’t be complete without some return fire. To that end, Tina Fey and Amy Poehler — the Ultron of comedy, whose powers only grow when they’re combined — deliver in spades.

Rest in peace Don Rickles. We don’t like you. We never did.