 He placed an emphasis on versatility and variety, writing many of his own songs and performing on a range of instruments – it was said of him in 1970 that he had written over 300 songs, as well as books, and played 14 instruments in styles that included country, blues, jazz, and pop.His first recordings were released as the 1959 album "Casey Sings Out", on the Urania label, which was recorded with a small group comprising Art Ryerson (guitar and banjo), Sandy Block (bass), and drummers Phil Krauss and Bunny Shawker.He moved to Elektra Records, which released the album "Goin' Places" in 1960, and recorded a one-off single on the Sutton label, "Freedom Rider", in 1961.