Don Rickles passed away on Thursday (April 6) at the age of 90, leaving behind a legacy as one of America’s all time great comedians.
Rickles was a two-time Grammy nominee in the best comedy album category for his albums Hello Dummy! in 1969 and Don Rickles Speaks! in 1970, but his career’s musical highlights exceed the award show.
From soundtracks to TV interviews, live performances and more, here are six of Rickles’ best music moments.
Don Rickles and Frank Sinatra on The Tonight Show Starring Johnny Carson
Rickles and Frank Sinatra were longtime friends and the two goofed on this relationship when Rickles surprised the iconic singer during an appearance on The Tonight Show Starring Johnny Carson. Here we get to see Rickles deliver a loving Sinatra impression and Sinatra tells a hilarious story about seeing the comedian at a restaurant one night.
Don Rickles Gives Larry King His Thoughts on Justin Bieber
When Larry King asked Don Rickles about his thoughts on Justin Bieber in 2014, the comedian was at a rare loss for words.
“If I Didn’t Have You” from Quest for Camelot
Rickles starred in the 1998 animated film Quest for Camelot as Cornwall, one of the heads on the two headed dragon Devon and Cornwall (Eric Idle played Devon). The two duet on a charming number where they wish for some space from their other half.
Don Rickles at the Just For Laughs Montreal Comedy Festival in 2014
Rickles lived up to his reputation as the “father of insult comedy” at the 2014 Just For Laughs Montreal Comedy Festival and even showed off some singing skills he surely picked up from hanging around Sinatra for all those years.
Don Rickles Sings “It’s Not Easy Being Green” on Muppets Tonight
Rickles guest starred in a 1997 episode of Muppets Tonight, which also featured Coolio, and for reasons too confusing to explain here wound up dressed as Kermit the Frog performing the character’s classic hit “It’s Not Easy Being Green” (skip to the four minute mark). It doesn’t go according to plan but is pretty fun regardless.
Mr. Potato Head’s “Midway Mania” Song From Disney World’s Toy Story Midway Mania! Ride
Disney fans will recognize Rickles’ voice as Mr. Potato Head from the Toy Story movies. And while Mr. Potato Head did not get his own song in any of the films, he did manage to get one for Disney World’s Toy Story Midway Mania! ride that’s sure to have you tapping your toes.