Don Rickles had the funniest Frank Sinatra story ever told

Come on. No one was too big to mock, and one of his favorite targets   was the charismatic and fearsome Frank Sinatra — the man no one teased, lest it be ring-a-ding-ding for them. It’s such a good story, it better have. It’s a credit not only to the comedic mind of Rickles, but to the good-sport nature of Sinatra that both men love that story, and both swear it really happened. A classic story repeated   so often at parties and on late-night TV that it has endured for decades. I’ll   let Frank tell it …

Come on. Don Rickles became famous as an insult comic, sarcastically nicknamed “Mr. One time, he crossed the line, all for an audience of one. Here’s Rickles telling it himself decades later on The Tonight Show again, this time to Jimmy Fallon instead of Johnny Carson. It was one of the bravest put-downs ever told. Show Full Article But it turned out to be   Sinatra’s favorite prank of all time. If there’s a heaven, I hope you’re in it and   giving God hell. Warmth” for his brutal putdowns of friends and foes alike. It doesn’t get better than that. Instead of trying to win over the audience, he made them his adversaries — and they adored   him for it. It’d be easy to ruin the joke by dissecting it, so I’ll just acknowledge the basic fact of why it’s so funny: Rickles had balls. As fellow headliners in Las Vegas during the early 1960s, Rickles often found himself   Rat Pack adjacent and became a favorite comic of Ol’ Blue Eyes, partly because he was one of the few willing to joke at   the singer’s expense. Rickles is the little bird who hops in to poke around the teeth of the alligator, and Sinatra kindly chooses not to slam his jaws shut and devour him. The audacity of it is so staggering, you can’t help but laugh, apparently even if you’re the one who was made the laughingstock. The comedian, who died Thursday at age 90, was fearless. Rest in Peace, Don Rickles.