This week, America lost its funniest late-night television guest. Don Rickles, the legendary “insult comic,” passed away at the age of 90.
Rickles accomplished many things in his long comedy career, from the early days of television to a late-in-life career resurgence with film roles in Martin Scorsese’s Casino and as the voice of Mr. Potato Head in Pixar’s Toy Story films, the fourth of which is scheduled to premiere in 2019.
But for many, Rickles will always be remembered for his literally hundreds of appearances on late-night television, beginning in the early days of The Tonight Show Starring Johnny Carson more than 50 years ago and continuing up until this past October when he sat down with Jimmy Kimmel for the last time.
Below is a look at some of his most memorable late-night appearances.
Rickles appeared on Johnny Carson’s Tonight Show alone more than 100 times, serving as guest host on occasion when Carson decided to take a few nights off. Sometimes, he would stop by seemingly uninvited, as he did on one night in 1976 when his friend Frank Sinatra was Carson’s lead guest. Midway through the interview, Rickles wandered onto the stage, and sat down beside Sinatra.
“I just was hanging around in the hall and they said Frank Sinatra’s here and I’ve never met him,” Rickles joked, before breaking into some mob-inflected Italian with the singer. Over the next several minutes, Rickles got up to belt out “My Way” and planted a big kiss on Sinatra’s lips. No one else could get a word in edgewise.
Rickles’ first appearance with David Letterman came in 1983, when the comedian’s Late Night show on NBC was still just getting off the ground. He immediately started ribbing Letterman for not being Johnny Carson, advised that bandleader Paul Shaffer get himself “committed” and spent as much time making fun of the musicians as he did talking to the host.
32 years later, Rickles appeared on one of Letterman’s final shows as host of The Late Show on CBS. Both Letterman and his other guest Howard Stern gave Rickles a long standing ovation when he sat down next to the desk.
When Rickles appeared on Late Night with Conan O’Brien in 1998, he was introduced by none other than O’Brien’s “Syncro-Vox” version of President Bill Clinton. Asked, “How are you?” at the top of the interview, Rickles deadpanned, “I was fine until I got on this.” He spent the next 20 minutes roasting O’Brien and his sidekick Andy Richter. “You’re not exactly the quickest guy in the world,” he told the host.
In 2008, Rickles sat down with Jon Stewart on The Daily Show and spent most of the interview gloating about his Emmy victory over both Stewart and Stephen Colbert, as well as David Letterman and Tina Fey, for his Mr. Warmth special on HBO. “You were weak, you and Stephen couldn’t make it!” Rickles said.
After telling The Tonight Show’s Jimmy Fallon that he loved his impressions and found him “fresh, funny and great,” Rickles told the host, “I want to tell you, from the bottom of my heart, I never liked you.” On that same show, he mocked Fallon’s recurring “Thank You Notes” segment. “When you turn that on, I take a shot at the wife,” he joked. It echoed a comment he made to Letterman about Fallon a year earlier: “I’d be on his show, but I don’t play ping-pong.”
No late-night host since Johnny Carson seemed to enjoy Rickles more than Jimmy Kimmel did. “Ninety years with Don Rickles weren't enough,” he wrote on Twitter today. “One of the sweetest and most lovely people I had the pleasure of knowing. We miss you already.”
When Rickles appeared on his show in late 2015, Kimmel asked him for his opinion of Donald Trump. This led to a story about the time Trump tried to sell him a condo. “I threw a dollar on the floor and said, ‘Leave me alone,’” Rickles joked. He added that he “wished him luck” in his run for the presidency, but the eyeroll that followed told a very different story.