President Ronald Reagan, Frank Sinatra, and Orson Welles were just a few of this targets.

By Derek Lawrence
April 06, 2017 at 05:43 PM EDT

Legendary comedian Don Rickles died Thursday at the age of 90. The king of insult comics, he found the perfect balance of making fun of people while earning their love at the same time, resulting in his preferred nickname of “Mr. Warmth.”

Well before Comedy Central brought roasts to a new generation, Rickles was making a career of insulting the biggest names in the world, whether it was President Ronald Reagan, Bob Hope, Dean Martin, or Frank Sinatra. In 2014, for the comedian’s 88th birthday, stars Tina Fey and Amy Poehler returned the favor.

See some of Rickles most memorable insults below.

On Orson Welles: “Orson Welles has been a great star for so many years. This man was married to a great many women in his life… they’re all flat now.”

On Frank Sinatra: “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.”

“When you enter a room, you have to kiss his ring. I don’t mind, but he has it in his back pocket.”

On Bob Hope: “Bob Hope couldn’t be here tonight, he’s looking for a war.”

On Ronald Reagan: “I must tell you, Mr. President, it’s a big treat coming out here all the way from California for this kind of money.”

“And the governor is the great politician of all-time, he laughs at anything. ‘My brother died.’ [Laughing like a dog] I tell you out there, America, our governor is dumb. That’s a joke, governor. [Dances around].”

RELATED: Watch 13 classic Don Rickles videos to remember the insult king

On Phyllis Diller: “Phyllis Diller, ladies and gentleman, who, when she was born, God ran out of clay and made her face trick or treat Charlie. Her former husband said on the wedding night, ‘Nooooo!'”

On Eddie Fisher/Elizabeth Taylor: “Eddie Fisher married to Elizabeth Taylor is like me trying to wash the Empire State Building with a bar of soap.”

On Ricardo Montalban: “I kid around about people, I got a reputation. Ricardo Montalban, a good friend, you know this. I got a reputation of being, like Newsweek said, ‘The merchant of venom destroys stars.’ You people in the back, this is not true. I love people, really. Ricardo, why do I kid you? Why? Because I don’t like you.”

On David Letterman: “It’s sweet of you, Dave — I know your busy schedule of going to the bank and trying to figure out what the hell you do.”

On Jerry Seinfeld: “He’s a wonderful guy. You talk to him, it’s like being alone.”