Rickles endeared himself to Frank Sinatra at their very first meeting. Sinatra had been encouraged by his mother to attend Rickles' comedy set in Miami, and Rickles spared no punches in ribbing the music icon. "I just saw your movie, The Pride and the Passion, and I want to tell you, the cannon was great. Make yourself at home Frank. Hit somebody."
Rickles joked about celebrities in attendance at his Friars Club honoring – "There are so many stars here tonight. As I look down the list – there's nobody big!"
Rickles joked about Bob Hope in the audience of The Dean Martin Show during the Vietnam War - "What's Bob Hope doing here? Is the war over?"
Rickles to President Reagan at his Second Inauguration – "I must tell you, Mr. President, it's a big treat coming out here all the way from California for this kind of money."
Rickles on his comedy - "If I were to insult people and mean it, that wouldn't be funny, there is a difference between an actual insult and just having fun."
Rickles on close friend Frank Sinatra - "When you enter a room, you have to kiss his ring. I don't mind, but he has it in his back pocket."
Rickles on retirement - "I'm in good health. I'm working better than I ever have. The audiences are great. Why should I retire? I'm like a fighter. The bell rings and you come out and fight. My energy comes alive. And, I still enjoy it."
Rickles on therapy - "I think if I took therapy, the doctor would quit. He'd just pick up the couch and walk out of the room."
Rickles on winning an Emmy for Outstanding Individual Performance in a Variety or Music Program - "Stephen Colbert's a funny man, but he's too young. He has got plenty of time to win awards, but this may be my last year and I think that I made it count. On second thought it was probably just a mercy award for an old man."
Rickles on his comedic style - "You know, every night when I go out on stage, there's always one nagging fear in the back of my mind. I'm always afraid that somewhere out there, there is one person in the audience that I'm *not* going to offend!"
Rickles' take on Martin Scorsese on the set of Casino – "Scorsese was our director. He had phone books under his ass so he could see the actors."