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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 first album Never Never Land remained on the Billboard Jazz Chart for over a year, and the Jazz Journalists Association voted it the Best Recording Debut. Her second album Come Dream With Me debuted at No. 1 on the Billboard Jazz Chart in May 2001. 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. She studied clarinet and music theory, and took the leads in theatrical productions in high school. She got her start performing on the South Shore of Long Island, and she began formal vocal training at the age of 17 at New York's Manhattan School of Music with Peter Eldridge, a founding member of the vocal group New York Voices. Began working on her first recording album after completing her studies at Manhattan School of Music in 1999. Considers Ella Fitzgerald as her foremost influence. Her other influences she says are Carmen McRae, Frank Sinatra, Mel Tormé and Irene Kral, groups Take Six, New York Voices, as well as non-jazz artists Barbara Cook, and singer/songwriters Bonnie Raitt and Joni Mitchell. 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. Married her college boyfriend, Rick Montalbano Jr., who is also the drummer in her touring band. During her college years, Monheit performed in the cabaret scene in Greenwich Village, New York City. Montalbano directed her toward jazz, by getting her to sing for his jazz quintet, which played frequently at a club in uptown New York.