Monheit grew up on Long Island. She began singing at an early age, which comes as little surprise given the musicality of her family: Her grandmother and aunt were professional singers, her father played banjo and her mother was involved in musical theater. At school, Monheit studied clarinet and music theory and participated in local theatrical and musical productions. After hearing Ella Fitzgerald and Sarah Vaughan, she realized that she wanted to be a jazz musician.
Monheit started working in clubs on the South Shore of Long Island while still in high school. Her formal vocal training began at age 17 at New York City's prestigious Manhattan School of Music, where she studied with Peter Eldrige, a founding member of the vocal group New York Voices. While in New York, Monheit moved into the cabaret scene in Village piano bars before her boyfriend convinced her to sing at the head of his jazz quintet.
In her senior year at the Manhattan School of Music, Monheit won the first runner-up prize at the 1998 Thelonious Monk Institute Vocal Competition. (The top award went to Teri Thornton.) Carl Griffin, head of artists and repertory for the multimedia company N2K, heard her there and offered her a record contract when she finished college in June 1999. Her first album, Never Never Land, was released in 2000, followed by Come Dream With Me in 2001 and In the Sun in 2002.
Jane Monheit's latest album, her 11th, is The Heart of the Matter, an eclectic collection of favorites spanning from Hoagy Carmichael to Lennon/McCartney to a Monheit original.