Groundbreaking comedian Don Rickles passed away today at 90-years-old.

DON RICKLES DEAD AT 90

Known as “The Merchant of Venom” and “The King of Zing,” Rickles perfected the art of insult comedy. He died as a result of kidney failure in his LA home. He was known throughout decades for his zingers and quick wit. Celebrate his life by reliving these funniest moments and fun facts from his life and career.

1. Rickles began performing at Murray Franklin’s, a small club in Miami Beach. In the 1950s, Frank Sinatra entered the bar with his entourage, and Rickles, who didn’t shy away from anybody, took aim. “Make yourself comfortable, Frank – hit somebody,” he said, referring to the singer’s infamous mood swings. “Frank, believe me, I’m telling you this as a friend: your voice is gone.” After that, Sinatra became of of Rickle’s biggest boosters.

A few years later, Rickles was on a date in a Las Vegas hotel when Sinatra again walked in. His date didn’t believe he knew Sinatra, so secretly Rickles approached the crooner’s table. He asked if the Rat Packer would come over to his table and simply say, “Hello, Don.” So a few minutes later, Sinatra strolls by and says, “Don! How the hell are you?” To which Rickles replies, “Not now, Frank! Can’t you see I’m with somebody?”

“Everyone stopped talking,” writes Rickles of the event in his 2007 memoir. “Everyone stared at us. Time stopped. And then, God bless him, Frank fell down laughing.”

2. Rickles became famous for roasting various celebrities, from Sinatra to Clint Eastwood to Ronald Reagan. Watch a few below.

3 Rickles actually played a role in all four Toy Story movies. While big names like Tim Allen and Tom Hanks made bigger waves, Rickles gave his voice to Mr. Potato Head. He reprised the role for three video games based on the franchise, as well as two TV movies – Toy Story of Terror! and Toy Story That Time Forgot.

“Well I’m a riot,” he joked. “The rest of the show is weak. I gotta be honest, the things I say are brilliant. Tom Hanks and Tim Allen, you know, timekillers.

4. Rickles won every award he was ever nominated for. In 2000, he was awarded with a star on the Hollywood Walk of Fame. In 2008, he got a Primetime Emmy for Individual Performance in a Variety or Music Program for his time in the 2007 documentary Mr. Warmth: The Don Rickles Project. He received the Legend Award in 2009 from TV Land, The Johnny Carson Award in 2012, and finally the Friars Club Lifetime Achievement Award in 2013.

5. Rickles was actually a very nice man, despite his genre of comedy. “If I were to insult people and mean it, that wouldn’t be funny,” he told the New York Daily News in 1996. “There’s a difference between an actual insult and a friendly jab. So I don’t think I’m offensive onstage. I like to think I’m like the guy who goes to the office Christmas party Friday night, insults some people but still has his job Monday morning.”

And in another 2000 interview, the comic reiterated that point: “Most people think the character I do onstage is the way I am offstage, but I’m just a regular guy who spends time with his family and who turns on the television and watches a lot of sports.”

Rickles wed his wife Barbara Sklar in 1965 when he was 38. “My tears are flowing; my life has turned to gold. My Barbara will be with me always,” he wrote upon recalling his wedding reception. But quickly was back to his old self, and joked about his friends, “Steve and Eydie, you sang beautifully, but I had no idea you’d ask for money.” Rickles is survived by Sklar, their daughter Mindy Mann, and their children Ethan and Harrison Mann.