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At the 1998 Thelonious Monk Competition, she took second prize to the late Teri Thornton, who was making a dramatic career comeback in the competition, shortly before her death. Monheit's performance led to her immediately being signed for her first solo recording Never Never Land, which placed her in the company of jazz veterans such as pianist Kenny Barron, bassist Ron Carter and saxophonist David "Fathead" Newman. Her musical family includes an aunt and a grandmother who were both professional singers, a brother who plays rock guitar, a father who plays bluegrass banjo, and a mother who performed in musical theater. Began working on her first recording album after completing her studies at Manhattan School of Music in 1999. Her duet single "I Won't Dance" (from album Taking a Chance on Love), featuring multi-platinum artist Michael Bublé, peaked at number 11 at the World Jazz Top 20 Singles - Year-End Chart in 2004. One son with husband Rick Montalbano born about 2006.