In 1957, Osmond auditioned for the the Eddie Haskell role, which was originally intended to be a guest appearance, but those involved with the show were so impressed with Osmond’s portrayal that the character became a key component of the series throughout its six-season run of 234 episodes.
Osmond portrayed Haskell as sycophantic to grownups while making fun of them behind their backs. He was a high-school friend of Wally Cleaver, older brother of Theodore “The Beaver” Cleaver, and constantly trying to get his friends in activities that would get them into trouble. During the final years of the show, Osmond was in the U.S. Army Reserve.