Jane Monheit was born on November 3, 1977, in Oakdale, New York, on Long Island, into a musical family: her father played banjo and guitar, her mother sang and took part in musical theater, and her grandmother and an aunt were professional singers. She grew up on records by Ella Fitzgerald, whom she credits as her first model, and Sarah Vaughan, and she also took in Judy Garland, Billie Holiday, and Broadway musicals. As a student she played woodwind instruments and piano, sang in award-winning choirs for about a decade, and worked in community theater on Long Island. She was already singing professionally while attending Connetquot High School in Bohemia, New York, and in clubs on the island's South Shore. She went on to the Manhattan School of Music, where she studied voice with Peter Eldridge, a founding member of the vocal group New York Voices, and graduated in 1999.

In her senior year she placed second at the 1998 Thelonious Monk International Jazz Vocals Competition in Washington, D.C. The top prize went to Teri Thornton, and Roberta Gambarini, who had just arrived in the United States, took third; Tierney Sutton also entered that year. Carl Griffin, head of artists and repertoire at the multimedia company N2K, heard her there and offered her a recording contract once she finished college in June 1999. Her debut, Never Never Land, was recorded at Sear Sound in New York on January 13 and 14, 2000, and released that year. Joel Dorn produced it, and the band was Kenny Barron on piano, Ron Carter on bass, Lewis Nash on drums, Bucky Pizzarelli on guitar, and Hank Crawford and David "Fathead" Newman on saxophones.

Come Dream with Me (2001), recorded at Sear Sound in January and February with Barron, bassist Christian McBride, drummer Gregory Hutchinson, trumpeter Tom Harrell, and, on two tracks, saxophonist Michael Brecker, reached number one on Billboard's jazz albums chart and was her breakthrough. In the Sun (2002) put her in front of orchestrations by Alan Broadbent and Vince Mendoza and brought Ivan Lins in on piano and vocal for his song "Once I Walked in the Sun"; it reached number five on the jazz chart. It was also the first of her records to include drummer Rick Montalbano, with whom she would work regularly and who is now her husband. Live at the Rainbow Room followed in 2003. In those years she also sang on other leaders' records, among them Terence Blanchard's Let's Get Lost (2001), Harrell's Wise Children (2003), and In Full Swing (2003) by violinist Mark O'Connor's Hot Swing Trio, where Wynton Marsalis plays on "Honeysuckle Rose."

Her major-label years began with Taking a Chance on Love (Sony Classical, 2004), the first of her albums produced by Peter Asher and Al Schmitt, with arrangements by Mendoza, Broadbent, Jorge Calandrelli, and Edward Shearmur and a duet with Michael Bublé on "I Won't Dance." It reached number one on Billboard's traditional jazz chart, and "Dancing in the Dark" earned a Grammy nomination for best instrumental arrangement accompanying vocalists. Her version of "Over the Rainbow" was used in the 2004 film Sky Captain and the World of Tomorrow. She followed it with a Christmas album, The Season (Epic, 2005), then moved to Concord for Surrender (2007), a set of ballads and Brazilian songs produced and arranged by Calandrelli, and The Lovers, the Dreamers and Me (2008), which mixed standards with songs by Paul Simon, Fiona Apple, and Corinne Bailey Rae and included "The Rainbow Connection." Bassist Neal Miner, by his own profile, has been in her band since 2007.

Home (EmArcy, 2010) debuted at number five on the jazz chart and featured John Pizzarelli and Peter Eldridge as guests. Her voice is also the one heard on the title song of the 2010 film Never Let Me Go, credited on screen to a fictional singer, Judy Bridgewater. The Heart of the Matter (EmArcy, 2013) was produced and arranged by Gil Goldstein and again reached number five on the jazz chart. In 2015 she recorded two albums with pianist David Benoit, 2 in Love and the Christmas album Believe. She then founded her own label, Emerald City Records, and opened it on April 8, 2016, with The Songbook Sessions: Ella Fitzgerald, a tribute to her first idol produced by trumpeter Nicholas Payton, with pianist Michael Kanan, Miner, Montalbano, percussionist Daniel Sadownick, and harpist Brandee Younger on two tracks.

She returned to the studio with her working group, led by Kanan as pianist and musical director, for Come What May (Club44, 2021), and added the holiday album The Merriest (Club44, 2022) with Pizzarelli. Jane Monheit (Club44, 2024), produced by Monheit and Montalbano, mixes standards and bossa nova and includes arrangements for the Nashville Recording Orchestra; her website calls it her thirteenth album and her first self-titled one, built from years of touring with her West Coast band. As of November 2026 her website lists her as living in Los Angeles with Montalbano, who is also the contact for her management company, Emerald City Artists, and their son. She also writes English lyrics for Lins, and her voice is on "Rio (Rio de Maio)" on his 2023 album My Heart Speaks.

Monheit is a warm, full-voiced interpreter of the Great American Songbook, with a swinging, flexible delivery that AllMusic describes as highly resonant, and she moves easily between standards, Broadway material, and the Brazilian and bossa nova repertoire she has recorded since In the Sun. Her models were Ella Fitzgerald above all, plus Sarah Vaughan, Judy Garland, and Billie Holiday, and she has paid direct tribute in The Songbook Sessions. She describes herself as a jazz and adult contemporary vocalist, and her records range from small-group jazz dates to lush orchestral productions with arrangers such as Mendoza, Broadbent, and Calandrelli, so her work sits between jazz and traditional pop; her albums have reached the top five of Billboard's jazz charts repeatedly and she has headlined clubs including the Village Vanguard and Birdland. Her teacher Peter Eldridge, her producers Joel Dorn and Al Schmitt, and her long-running rhythm section of Kanan, Miner, and Montalbano shaped the sound of her records; she also teaches and mentors students.