Chertoff attended the University of Pennsylvania, and whilst in Philadelphia he met soon-to-be long-time friends Rob Hyman and Eric Bazilian and formed a lasting musical collaboration. Chertoff played drums in a local band "Wax" with Hyman and later produced and played with the band Baby Grand, which included both Hyman and Bazilian. He was a force behind the signing of Hyman and Bazilian's later band, The Hooters to Columbia Records, where he produced their multi-platinum albums, Nervous Night, One Way Home, and Zig Zag.[2]
One of Chertoff's biggest successes in his Columbia days was producing Lauper's debut album, She's So Unusual. The album sold 9 million copies with hits such as "Girls Just Wanna Have Fun", "All Through the Night", "When You Were Mine" and "Money Changes Everything." He brought together Hyman and Lauper who co-wrote the #1 hit, "Time After Time." Lauper and Chertoff then teamed up to write the hit, "She Bop."[3]
In 1992, Chertoff started his Blue Gorilla label at Polygram. Blue Gorilla issued Joan Osborne's Relish, a multi-platinum album and worldwide hit which also garnered 7 Grammy nominations, including 'producer of the year'.
Largo is based on the second movement of Dvorak's "Symphony from the New World." The album, which Chertoff co-produced and co-wrote, features David Forman, The Chieftains, Taj Mahal, Garth Hudson, Levon Helm, Lauper, Osborne, Carole King, Hyman and Bazilian and uses Dvorak's journey to America as a tapestry of American blues and folk music. He is in collaboration to bring Largo to the stage.