The Sublime Joy of a Don Rickles Insult

Don Rickles was the avatar, the alpha and omega, the platonic ideal for several beloved American cultural notions that now exist only as quaint historical fantasies: the insult comic everybody loves. The mobbed-up, or at least mob-tolerated, literal wiseguy with no blood on his hands, or his clothes. (Seriously: Rickles boasted that he once told a gangster, from the stage, that the gangster’s wife looked like a moose, and survived.) Las Vegas in its seedy, pre-Disneyfication heyday. Frank Sinatra mega-worship, back when young people knew Frank Sinatra as more than just a guy who had a cold once. The notion that “late-night-talk-show guest” could be a viable art form and a legitimate career.

Rickles died Thursday of kidney failure at 90; he outlived the vast majority of the context for why he was so great, so feared, so tolerated, so beloved. Upon hearing the news, this was, roughly speaking, my first thought.

My second thought was “David Letterman.”

The opening clip in this amateur tribute is lovely in that it combines many of Rickles’s finest selling points. Letterman’s prompt: “Give us an idea of how Las Vegas has changed in 51 years.” And the man known semiprofessionally as “Mr. Warmth” is off, sketching out a sand-swept, goon-infused, Sinatra-placating wonderland, peaking with the line, “And they all sat around, smelling their guns.” He makes Letterman laugh like a hyena, at such velocity and length that he stops only when he has a coughing fit.

In subsequent clips, Rickles appears at various fetes and whatnot, lambasting various big shots to their invariably delighted faces. Martin Scorsese (“Marty, when we see all the films you did, none of them were great”). Bob Hope (“Do us a favor: Get off the air”). Sinatra (“I must tell you, Frank: It’s all over for you, Frank”). It’s hard to articulate how these jokes work, how they qualify in the moment as jokes at all. But they do. What an odd legacy, to say mean things about people that make everyone convulse with joy, the intended target most of all. What a testament to your ability that you can do that all your life, in the highest echelons and on the biggest stages, and still die beloved as ever.

The trick is to let the rabbit hole open beneath you naturally. From the cheerful Marty/Bob/Frank slander, you’re drawn to what both Rickles scholars and the man himself often cite as a career highlight: roasting President Reagan at a second-inaugural gala. Mr. Warmth’s first verbal shot is directed at his lead-in, who is Emmanuel Lewis, a.k.a. Webster, which is incredible — almost as incredible as the fact that Rickles’s joke is, “First black kid I ever saw that’ll definitely never play basketball.”

What follows is manic, bonkers, fearless, and not always palatable. His best line is, “Is this too fast, Ronnie?” His half-serious thesis statement is almost funnier, in that most of it, at least, is true: “I make fun of the president. Why not? I make fun of everybody. That’s America. Laughing. Charlton Heston, I’m a friend: It’s over.” It’s enough to make you dizzy, and a little squeamish.

You’re gonna read some takes about Don Rickles in the next 72 hours. This is one of those situations where only one person on earth could do a thing well — could wrap a reverent slab of compassion in a thin shell of jovial cruelty, like a layer of foil around a solid-chocolate Easter bunny — without the cruelty curdling into something merely ugly. Try to do what Don Rickles did and you wind up sounding like a Twitter egg, like a human YouTube comments section, like an unfeeling cesspool. The trick was to take him seriously, but not literally.

Follow the rabbit holes and you wind up back on Letterman.

Here we have Don in 2008, ostensibly promoting the documentary Mr. Warmth: The Don Rickles Project. The reason to watch this is that Denzel Washington is sitting next to him during the whole bit, losing his damn mind. I will confess that for a long time I was, if not particularly anti-Rickles, then not particularly pro-Rickles, wincing as I instinctively do at anything that involves heckling, conflict, discouraging words. The trick is to push past that discomfort, to go deeper and realize that for once there’s actual depth to it — a humanity cleverly disguised as inhumanity. The old line is that it was an insult not to be insulted by Don Rickles, that a joke from him at your expense was priceless, the best compliment you could ever hope to receive. He mocked indie-rockers, talk-show hosts, presidents. They were all grateful, and so were we. It makes no sense. But that’s comedy. That’s America.