Kleinow was born and raised in South Bend, Indiana; inspired by Jerry Byrd, he took up the pedal steel guitar in high school. Following graduation, he was employed for over a decade as a maintenance worker at the Michigan Department of Transportation. In 1963, he relocated to Los Angeles, where he began a career as a visual effects artist and stop motion animator in the film and television industry. After uncredited work on "The Wonderful World of the Brothers Grimm" (1962), "The Outer Limits" (1963–1965), and "7 Faces of Dr. Lao" (1964), Kleinow became closely associated with the long-running children's series "Gumby" and "Davey and Goliath" while moonlighting in the city's country-oriented nightclubs as a member of Smokey Rogers & the Western Caravan (from which his distinctive nickname originated) and the Detours (often deputizing for bandleader Red Rhodes, then concurrently employed as a session musician).