"[3] His major recordings included "Slippin' Around", "Red Hot Mama" in 1924 with Sophie Tucker on vocals, "Miff's Blues", and "There'll Come a Time (Wait and See)", which is on the film soundtrack to the 2008 movie The Curious Case of Benjamin Button.

[5] From 1918 to 1919 Mole played in the Acme Sextett with Benny Krueger (saxophone), Ernie Holst (violin), and Edwin Taylor Williams (banjo).

Mole and his band, which included Eddie Lang, Jimmy Dorsey, Red Nichols, and Vic Berton, also accompanied her for live performances.

The original Five Pennies band consisted of Nichols on cornet, Mole on trombone, Jimmy Dorsey on clarinet and alto sax, Eddie Lang on guitar, Arthur Schutt on piano, and Vic Berton (who came up with the name for the group) on drums, but over time the personnel changed and expanded.

Mole's solo style, which included octave-leaps, shakes, and rapid-fire cadenzas, had a profound effect on jazz trombone playing in his time.

In 2008, his composition "There'll Come a Time (Wait and See)", written with Wingy Manone, was on the soundtrack to the Academy Award-nominated movie The Curious Case of Benjamin Button.