One of Osborne's early television appearances was in a 1959 episode of "Westinghouse Desilu Playhouse" called "Chain of Command", starring Hugh O'Brian. He was also featured in the Christmas Day "Desilu Playhouse" installment "The Desilu Revue" in December 1959. He also had small roles in such TV shows as "The Californians" and the 1962 pilot episode of "The Beverly Hillbillies", "The Clampetts Strike Oil" (in the role of Jeff Taylor). He refrained from signing on for the series, however, thinking the show would not be a success, and instead focused his attention on acting in television commercials.