Rickles had a career that spanned over 60 years. He became known for his quick wit and sharp insults, which he aimed at both his friends and his fans. He had a special talent for turning the tables on hecklers, which helped him stand out in the world of comedy. His career took off after he made a name for himself as an insult comic, always ready with a clever put-down.

One of the most famous stories about Rickles involves him insulting Frank Sinatra. When Sinatra showed up late to one of Rickles’s shows in the 1950s, Rickles didn’t hesitate to poke fun at him. He joked about Sinatra’s violent reputation and even told him his singing voice was gone. Despite this, Rickles’s comedy style earned him the respect of people, even the biggest stars.

In real life, Rickles was nothing like the harsh persona he portrayed on stage. He was a devoted family man, living with his mother until he married at 38. His marriage to Barbara lasted until his death. Rickles was well-loved by his friends, and he had a special place in the Rat Pack, even though he wasn’t quite like the others in the group. His friendships and influence in Hollywood were vast, and he was admired by people like Carl Reiner, Bob Newhart, and Sidney Poitier.

Rickles was also a mentor to many younger comedians, helping them with their careers. Comedians such as David Letterman, Jimmy Kimmel, Louis C.K., and Chris Rock all looked up to him. His kindness and support helped shape the next generation of comics.