Irving Milfred Mole, known professionally as Miff Mole was a jazz trombonist and band leader. He is generally considered one of the greatest jazz trombonists and credited with creating "the first distinctive and influential solo jazz trombone style."
His major recordings included "Slippin' Around", "Red Hot Mama" in 1924 with Sophie Tucker on vocals, "Miff's Blues", "There'll Come a Time (Wait and See)", on the film soundtrack to the 2008 movie The Curious Case of Benjamin Button
Miff Mole was born in Roosevelt, Long Island, New York. He studied violin and piano as a child and switched to trombone when he was 15. He played in Gus Sharp's orchestra for two years and in the 1920s went on to become a significant figure of the New York scene: he was a member of the Original Memphis Five (1922), played with Ross Gorman, Roger Wolfe Kahn, Sam Lanin, Ray Miller and many others. His other activities, like those of many jazz musicians at the time, included working for silent film and radio orchestras. In 1926–29, he and trumpeter Red Nichols led a band called Miff Mole and His Little Molers. They recorded frequently until 1930.
Mole and his band backed Sophie Tucker, who was known as "The Last of the Red Hot Mammas" and who was one of the most popular singers of the 1910s and 1920s. They accompanied her on her 1927 Okeh recordings of "After You've Gone", "Fifty Million Frenchmen Can't Be Wrong", "I Ain't Got Nobody", and "One Sweet Letter from You". Mole and his band, which included Eddie Lang, Jimmy Dorsey, Red Nichols, and Vic Berton, also accompanied her for live performances.
From 1925 to 1929 Mole was identified with bands led by cornetist Red Nichols: The Red Heads, The Hottentots, The Charleston Chasers, The Six Hottentots, The Cotton Pickers, Red and Miff's Stompers, and especially Red Nichols and His Five Pennies. These bands recorded for the labels Perfect, Domino, Pathé, Edison, OKeh and Victor, though the Five Pennies name was used only for their recordings on Brunswick. 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. Among the musicians who passed through the Five Pennies were clarinetist Pee Wee Russell, violinist Joe Venuti, bass saxophonist Adrian Rollini, tuba and bass player Joe Tarto, trombonist Glenn Miller, and extra trumpeters such as Leo McConville and Charlie Teagarden.