Don Rickles and Why the Best Friendships Are Based on Roasting Each Other

If there’s anything we can take away from the life of Don Rickles, it’s that the strongest of male friendships are predicated on ruthlessly making fun of each other.

Rickles died last Thursday of kidney failure, and his legacy will be that of the original insult comic. No person or subject was too taboo for Rickles. He told gay jokes, Polish jokes, black jokes, Jewish jokes and Italian jokes, as well as brutally cutting jokes about the biggest stars in the world — often right to their faces.

Among his favorite targets was the otherwise untouchable Frank Sinatra:

There’s a part in Gay Talese’s legendary Esquire profile “Frank Sinatra Has a Cold” where Sinatra goes to see Rickles perform at The Sahara in Vegas. Sinatra is surrounded by his usual crew of sycophants when Rickles starts laying into him. Sinatra was a star of unmatched renown, and he lived in an era when celebrities could still maintain a veneer of infallibility and were idolized accordingly. Only Rickles had the chutzpah to call Sinatra out on his failing marriage, his failing hair and his failing voice — and that was before the goof’s about Sinatra’s Italian heritage and reputed mob ties.

That’s largely why Rickles’ jokes about Sinatra were so funny — they pierced the otherwise impenetrable halo of celebrity that surrounded Sinatra, and provided a release valve. But it’s also why Sinatra loved Rickles so much. In a life full of yes-men and hangers-on, Rickles treated Sinatra like an equal. (At the show mentioned in “Frank Sinatra Has a Cold,” Sinatra’s cronies only laugh when he does, or basically the moment they know he’s not offended.)

Gender studies experts might say the reason male friends are mean to each other is that society conditions men to suppress their emotions, lest they be punished by other men and labeled cucks. Instead, they feel the need to mask their feelings with teasing.

But good-natured ball-busting between male friends is an expression of admiration. It says, “We’re such good friends that I can make a joke at your expense, and it’ll have no effect on our friendship. In fact, it will strengthen it.”

Psychologists call this “prosocial” teasing and maintain that it’s healthy for friendships. “You take something about some individual and, in making a lighthearted comment, you’re accepting them, even loving them,” Mark Barnett, a developmental psychologist at Kansas State University, tells Quartz.

In other words, as Rickles knew best, we troll because we love.