Miff Mole started his musical career playing violin and accompanying silent pictures on the piano, but later he switched to trombone. His career in jazz music began with Gus Sharp's Orchestra; he then went on to play with band leader/comedian Jimmy Durante. He joined the Original Memphis Five and played on and off with them until 1924. In 1923 he met Red Nichols and went on to make many records with bands directed by Red Nichols or under the name of Miff Mole and his Little Molers. However in 1927 he started working as a studio musician and Mole played very little Jazz during the next couple of decades. He played with Paul Whiteman during 1938-40 and was with Benny Goodman in 1943. He returned to small-group jazz in the mid-1940s playing with Eddie Condon and recording for Commodore under the name of Miff Mole and his Nicksieland Band. Mole's health declined in the 1950s and he was largely forgotten by the greater jazz world by the time of his death in 1961.