For over six decades, Don Rickles was a living comedy highlight reel. Whether he was roasting his own audience during a stand-up routine, bringing talk-show-host veterans to tears with laughter or acting alongside the biggest movie stars in the world, all of Rickles’ performances were one of a kind.
The legendary insult comic died on Thursday at the age of 90. His longtime representative Paul Shefrin told PEOPLE in a statement: “Emmy-Award winning iconic comedian Don Rickles passed away at his home Los Angeles this morning (Thursday) as a result of kidney failure.”
While younger generations will remember him as the voice of Toy Story’s Mr. Potato Head, Rickles has been making people laugh since the ’50s, first as a stand-up, then as a popular guest on late-night shows and finally as a television and movie actor, making lifelong friends out of costars like Joan Rivers, Frank Sinatra’s Rat Pack, Martin Scorsese and Clint Eastwood.
Below are a collection of some his most memorable moments, many of which include his trademark insult comedy, which he fearlessly wielded against all types, regardless of race, religion or fame.
WARNING: CLIPS CONTAIN EXPLICIT LANGUAGE
Rickles was considered an honorary member of Sinatra’s Rat Pack, and he was also a favorite guest of Johnny Carson’s Tonight Show. In one of the funniest moments of Carson’s late-night tenure, Rickles surprised the crooner during an interview in 1976.
Another classic moment between Rickles and Sinatra, this time at a comedy roast for the singer two years later in 1978.
Rickles has CNN’s Larry King in stitches during this 1985 appearance on Larry King Live.
Rickles starred with Clint Eastwood in 1970’s Kelly’s Heroes and the two became close. But that didn’t stop the comedian from unleashing his patented stream of insults at Eastwood and his guests during a 1986 tribute show.
Another classic Carson interview on The Tonight Show in 1978.
Rickles tears into The Tonight Show’s new host Jay Leno in 1994, who had taken over the job from Carson two years earlier.
By 1995, Rickles had reenergized career with starring roles in Toy Story and Casino, but he didn’t lose a step sparring with David Letterman. “Don coming on our show was always a highlight for me,” Letterman said in a statement on Rickles death. “Just endless mischief and nonsense, and a guy who would make the audience go completely crazy. Such a professional, such a gentleman. I already miss him.”
Even presidents weren’t safe. Ronald Reagan was on the receiving end of one of his funniest roasts ever during the president’s second inauguration in 1985.
Rickles appeared on the TV series Get Smart, which ran from 1965-1970. Above, Rickles and costar Don Adams’ behind-the-scenes antics were recorded for a blooper reel.
Rickles lent his iconic voice to the Mr. Potato Head character in 1995’s Toy Story and became one of the film’s most lovable characters. He continued to voice the character in subsequent Toy Story films and shorts.