Frank Sinatra Reflected on a Stunning Prank by Don Rickles: ‘I Stood With My Mouth Open’

Frank Sinatra’s quick temper and alleged mob ties meant that most people did not poke fun at him for fear of harsh retaliation. Most people besides comedian Don Rickles, that is. Rickles was an insult comic who had no fear of Sinatra. Once, he took a risk by playing a prank on the singer at a restaurant. Sinatra recounted the story for laughs.

Don Rickles was one of the few people who could publicly insult Frank Sinatra

Everyone who knew Sinatra was aware that he could oscillate between love and anger. When insulted, his retaliation could be harsh.

“Sinatra’s character flaw isn’t hard to name,” wrote Adam Gopnick for The New Yorker. “He lived in daily fear of humiliation, and in its (often imagined) presence his temper tipped over in an instant.”

Most people tried to avoid insulting Sinatra so that he didn’t retaliate. Rickles, however, wasn’t afraid to poke fun at the singer’s temper. Once, he shouted out to Sinatra when he entered an event, per the Washington Post.

“Hey, Frank, make yourself at home,” Rickles said, before adding, “Hit somebody!”

The room watched with bated breath, waiting on Sinatra’s reaction. Rickles knew that he could have ruined his career if the joke went over poorly. Luckily, Sinatra reacted well. The two men were close friends, despite the ribbing. 

He once played a prank on the singer

On another occasion, Rickles played an insulting prank on Sinatra for his date’s sake. In an appearance on The Tonight Show, Sinatra himself recounted the moment to Johnny Carson and the audience. 

“Can I tell a story about what this man did to me once?” Sinatra asked. “You may have known or heard about this. It’s a true story. This was a long time ago, long before Don got married. I was eating dinner at a restaurant in New York, and I was sitting with some friends, and he came over to the table, and he said, ‘Frank, do me a favor, will you?’” 

Sinatra explained that Rickles was on a date. He’d bragged about his connection to Sinatra, but his date didn’t believe him. Rickles hoped that Sinatra would come over later and say hi as proof of their friendship. 

As Sinatra was nearing the end of his meal, he agreed to this plan. When he finished his espresso and walked over to Rickles’ table, however, things didn’t go as he expected.

“I said, ‘How are you, Don? Nice to see you,’” Sinatra explained. “He said, ‘Can’t you see I’m eating, Frank? What are you doing?’”

Sinatra said it was hard to cover his shock.

“I went through the whole thing,” he said. “I stood with my mouth open.”

Frank Sinatra and Don Rickles were friends for life

Rickles had a penchant for pushing Sinatra’s buttons, but the two men remained friends for years. Sinatra threw parties for Rickles and, after Sinatra’s death, Rickles served as a pallbearer. Despite Sinatra’s intimidating reputation, Rickles saw the warmth in the singer.

“He was the most charming, terrific man in the world,” Rickles said. “He really was. He was fun to be with.”