Straight started his career in 1909 accompanying singer Gene Greene in Vaudeville. In 1916, he began working at the Imperial Piano Roll Company in Chicago, where he recorded dozens of piano rolls. He became a popular bandleader in Chicago during the 1920s. His band, the Charley Straight Orchestra, had a long term engagement at the Rendezvous Café from 1922 to 1925 and recorded for Paramount Records and Brunswick Records in the 1920s.