His biggest hits were made during the 1920s and early 1930s, including popular phonograph records of "Frankie and Johnnie", "Abdul Abulbul Amir", "A Gay Caballero", "The Prune Song", "There's No-one With Endurance Like The Man Who Sells Insurance", "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 sometimes accompanied his singing on ukulele.

Crumit married Julia Sanderson in 1927.