While still in high school, Tillotson was making records and performing on stage; as a student at the University of Florida, he had his own musical variety show on regional television. Following graduation in 1959 with a Bachelor's Degree in Journalism and Communications, he signed with Cadence Records and moved to New York City to pursue his music career. In 1960, he recorded his first hit, a composition entitled "Poetry in Motion" (written by Anthony/Kaufman), that went to #2 on the Billboard Hot 100 in the U.S. and #1 on the UK Singles Chart.