He was drafted into the United States Army and served in the Korean War with an artillery unit, later being transferred to an entertainment unit. It was in his traveling-musician days that Daily began performing stand-up and gradually began playing some of the bigger clubs in the country. He appeared in guest spots on My Mother the Car, The Farmer's Daughter, and Bewitched. Veteran sitcom writer Sidney Sheldon liked Daily's work and hired him for a supporting role on I Dream of Jeannie. In 1972, two years after Jeannie was canceled, Daily was back on television as Howard Borden in The Bob Newhart Show. In 1980, Daily was offered his own show, called Small & Frye.