Route 66 was a constant in Bob Waldmire’s life. His parents, Edwin and Virginia, started the Cozy Dog Drive In along it in 1946. In 1962, when the Waldmire family took a road trip to California via the famed route, Bob was introduced to the American Southwest. He was hooked to both Route 66 and the desert for the rest of his life. Soon after graduating high school, the budding self-taught artist took to the road. Years later, he would tell The Chicago Tribune that, "The main reason I became traveling artist was to avoid having a real job. It was about being free to move. Wanderlust."