Hentoff began her teaching career at the Harlem School of the Arts, where she taught music theory, ear training, composition and jazz piano. She also taught music theory and composition for the preparatory divisions of The Juilliard School and Manhattan School of Music. Hentoff has lectured on music and arts education for The Kennedy Center in Washington, D.C. and The Juilliard School in New York City.

Hentoff has performed extensively as a singer/songwriter. She released her first solo CD, In This Room, in 1999. In addition to writing all of the songs and singing lead vocals, Hentoff played keyboards and co-produced the album. She is also the creator of Mandy’s Menagerie, a multi-media children’s entertainment property that features original songs sung by kids. Hentoff has written, produced and recorded all the music for the property. She has also created, designed and illustrated its characters in a distinct and endearing visual style.