Five-foot-six, forehead-mopping Don Rickles was on the verge of hitting the big time. After years of insulting his way up through strip joints and shady supper clubs, he’d made his way to California (or in some versions of this story, Miami Beach). On this night, like most others, he stalked the stage identifying easy marks in the crowd -- the overweight, the less-than-handsome, the balding -- and delivering a machine-gun torrent of piercing put-downs. Ethnic, gender and religious lines were crossed without mercy. Rickles was a comedy killer and the crowd loved him for it. 

This particular night would go a long way to creating the Rickles legend, if only because he retold the story so many times. The comic was spraying slurs on stage when Frank Sinatra -- famously volatile Frank -- walked in. He took a seat with his boys (you can picture them) at a table directly in front of Rickles. Nobody insulted Sinatra to his face, not even Joey Bishop. Would Don dare?  Hell yes, he would.

Make yourself comfortable, Frank. Slug somebody.

There must have been an excruciating moment of tension before Sinatra snickered, cueing everyone in the room that it was OK to let loose with laughter. For Don and Frank, it was the beginning of a beautiful show-biz friendship.

But could it happen today? If Will Smith can jump the stage at the freaking Academy Awards to smack Chris Rock for a joke about Jada (wife barbs were a Rickles specialty), the stakes have been raised. Earlier this month, comic Ariel Ellis engaged in seemingly friendly banter with audience members about politics -- and a heckler chucked a beer can at her head. It seems like no one is laughing anymore. 

Does that make Rickles a historical relic?  Michael Seth Starr, author of the upcoming biography Don Rickles: The Merchant of Venom, told Cracked that we may never see anything like Rickles’s career again. 

That era is over

In the 1960s and 70s, you could barely change the television channel without seeing Rickles ripping some celebrity a new one. Don guested on virtually every sitcom around, though he was probably best known for appearing more than 100 times on The Tonight Show with Johnny Carson. Carson basically gave Don, a man he personally nicknamed “Mr. Warmth,” the extremely rare open invitation to drop in at any time, even during other guests’ segments.

But the best TV spot for Don’s talents was the Dean Martin Celebrity Roasts, the grandfather of the Jeffrey Ross/Comedy Central versions of more recent vintage. Everyone from Sinatra to Lucille Ball to Ronald Reagan took turns bearing the brunt of celebrity barbs, and the clean-up hitter was always Don Rickles. Who could follow the Merchant of Venom?

“Don was the only person who they never wrote for on those roasts,” says Starr, noting that an astronaut making fun of a celeb like Nipsey Russell was going to need some help on the joke front. “But they never wrote for Don because he just basically did his act.” 

As the years passed, Rickles became a beloved elder statesman of comedy, known more for the cuddly voice of Mr. Potato Head in the Toy Story movies than for his devastating discourtesies. And that may have been in part because his brand of insult comedy no longer flew. 

“Listen, he was of his time,” says Starr. Rickles came of age in “the era when it was OK to make fun of ethnic groups. It was just accepted and if people groused about it, they groused about it in private.” 

Just what kind of “gags” are we talking about? Try this one that Rickles dropped at the American Film Institute’s tribute to Shirley MacLaine in 2012. President Barack Obama was in attendance and Rickles wasn’t going to let a new era’s political correctness stand in his way. “President Obama is a personal friend of mine,” he quipped. “He was over to the house yesterday, but the mop broke.”

The joke, notes Starr, went over like a lead balloon. The line was cut out of the broadcast (gee, you think?) but Rickles was seemingly given a pass by the crowd, a comic in his late 80s who just didn’t get it. 

But it’s a big reason Starr believes Don’s routines wouldn’t translate to today. While entertainment outlets like The Hollywood Reporter reported on the Obama bit, most people weren’t aware that it happened.  With social media’s megaphone amplifying the story today, Rickles wouldn’t be going on stage again anytime soon, says Starr. “Or he would be on an apology tour.”

Then again, it’s not hard to imagine a younger version of Rickles adapting to whatever constitutes today’s acceptable version of “mean.” He seemed to have a sixth sense, says Starr, about when he was going over the line. The line was different in 1965 at the Saraha in Vegas, but the concept is the same for today’s roastmasters like Jeffrey Ross.

For as apparently cruel as Ross can be to roasted celebrities like Charlie Sheen or Donald Trump, “I'm pretty careful about the things I say,” he told NPR. “I'm thoughtful about not going too far.” 

Like Starr, Ross was in awe of Don’s ability to sense what an audience could handle. “He was a scientist when it came to people’s personalities and vulnerabilities,” he told Rolling Stone. “It was almost surgical. It might look random to the audience, but from the comedian’s perspective, I don’t know if anybody will ever work a room the way he did.”

There are so many things about Rickles’s act that wouldn’t fly in 2022. Telling an audience member his wife looked like a moose. Making jokes about someone being Black or a Jew, an Asian or a Catholic, a Hispanic or a German. Rickles had quips for all of them. What does it say about 1960s audiences that being on the receiving end of such comic slaps, at least from Rickles, was perceived to be a badge of honor? And what does it say about audiences today that those insults might be returned with a hurled can of beer?

Ironically, Rickles always ended his act with a plea for brotherhood, a “can’t we all get along?” sermon that preached the importance of being able to laugh at ourselves. It was more than a little disingenuous -- Mr. Warmth got to dish it out for an hour but he didn’t have to take it. (His own feelings were easily bruised by poor reviews.)  So perhaps social media would have done Rickles in after all, not by canceling him but with its unrelenting criticism.  

As for insult comedy, history tells us it will live on in evolved forms, with ever-shifting guardrails that savvy comics will avoid (or purposely demolish). It’s not all on the comics -- audiences will have to play along, providing space to figure out works. We need to let comedians take big swings and try stuff and not hold them accountable for every little word that comes out of their mouths,” says Ross. “I’m sure Picasso’s rough drafts weren’t as nice as his finished paintings.”

Top image: Flashback - Rhino Records

Get More Comedy: Sign up for ComedyNerd

The ComedyNerd newsletter is your weekly look at the world of stand up, sketch, and more. Sign up now!

Forgot Password?