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 musical collaboration that has lasted to this day. 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 major 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.
Chertoff's A&R career began under the training of music legend Clive Davis at the inception of Arista Records. In his all-purpose A&R/production role, Chertoff signed and produced, edited and remixed tracks for many Arista artists including The Kinks and the Alan Parsons Project. Chertoff’s Arista career culminated in his co-production of Air Supply’s first million-seller, Lost in Love as well as his co-production of the theme from Steven Spielberg's Close Encounters of the Third Kind with acclaimed composer John Williams.
In 1980, Chertoff joined Columbia Records, rising to Senior Vice President of A&R in 1989. Over the next three years, while heading the A&R department, he oversaw the creative efforts of dozens of careers. He signed artists such as The Band and Sophie B. Hawkins, and brought in label deals such as the successful Ruff House Records which resulted in albums from The Fugees, Lauryn Hill, Wyclef Jean, Kris Kross, and Cypress Hill.
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 perennial 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 smash, "Time After Time." Lauper and Chertoff then teamed up to write the hit, "She Bop."
In 1992, Chertoff started his Blue Gorilla label at Polygram to allow him the opportunity to get back to concentrating in the studio on a select roster of artists. Blue Gorilla immediately performed well, exceeding expectations, with Joan Osborne' Relish, a multi-platinum album and worldwide smash which also garnered an amazing 7-Grammy nominations, including ‘producer of the year.’
Chertoff co-wrote and co-produced the song "Christmas of Love" for Ron Howard’s film How the Grinch Stole Christmas and he co-wrote and co-produced the theme for Jerry Zucker’s film, Rat Race with Jon Carin from Pink Floyd & songwriter David Forman, who also performed the lead vocals for each song.
He is currently producing The Dream Jam Band, a group that writes and performs music for family audiences.
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 timeless tapestry of American blues and folk music. He is currently in collaboration to bring Largo to the stage.