His biggest hits were made during the 1920s and early 1930s; they included popular phonograph records of "Frankie and Johnnie", "Abdul Abulbul Amir", "A Gay Caballero" (he even recorded a sequel, "The Return of a Gay Caballero"), "The Prune Song", "There's No-one With Endurance Like The Man Who Sells Insurance", "Down In De Canebrake", "I Wish That I'd Been Born in Borneo", "What Kind of a Noise Annoys an Oyster?", and "I Learned About Women From Her". Crumit is credited with composing at least 50 songs in his career, including the Ohio State University fight song, "Buckeye Battle Cry" in 1919 for a song contest. Prior to this he wrote at least two songs for Ohio University, “Round on the Ends” and “OH + IO.” He composed and published "Hills of Ohio" in 1941. His song "Donald the Dub" was used as the theme music to the BBC radio adaptation of P. G. Wodehouse's "Oldest Member".