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Known to most as a stand up comic, Winters took dramatic turns on occasion, guesting on an episode of The Twilight Zone, and did extensive voice over work, including Pogo for President: I Go Pogo, Dr. Seuss' Daisy-Head Mayzie, Animaniacs, Garfield and Friends, The Completely Mental Misadventures of Ed Grimley, Alice Through the Looking Glass, and The Smurfs,
Winters also made a cameo in the feature film adaptation of The Flintstones (featuring effects from Jim Henson's Creature Shop), was a regular on Hollywood Squares, and his most famous film role was that of aggressive truck driver Pike in It's a Mad Mad Mad Mad World.