Her work is known for its emotional intensity, with her writing exploring nature, love, loss, death, myth, and identity, often with philosophical and literary influences.

Her mother also used to be a torch singer in Washington clubs, so Jennifer also learned early on the songs of Édith Piaf, Ruth Etting, Marlene Dietrich, Billie Holiday, and Judy Garland.

At age 12, she became passionate about the music of South Asia after her mother returned from a journey across India and Nepal with a bag full of cassettes for her, with Jagjit and Chitra Singh's The Gold Disc being her favorite.

Her mother had season tickets to the National Symphony Orchestra, which they attended on Friday nights, and her father would take her to hear live jazz at places like Blues Alley, One Step Down, and Charlie's Georgetown, where she saw the likes of Anita O'Day, Mel Tormé, Dizzy Gillespie, Ahmad Jamal, Oscar Peterson, George Shearing, and Jamaican jazz pianist Monty Alexander.

She was turned on to the different sounds in each city - The Lounge Lizards, Diamanda Galas, Lydia Lunch, Blondie, and The Velvet Underground in New York; and The Specials, Gang of Four, Siouxsie, The Slits, The Buzzcocks, The Birthday Party, Cocteau Twins, and The Fall in the UK.

She also grew up going to go-go concerts, seeing Chuck Brown, Trouble Funk, Junk Yard Band, E.U., and Rare Essence, and went to hear Ethiopian music in the clubs and restaurants of DC's Adams Morgan neighborhood.

In 1987, she moved to New York to continue her theatre and academic studies, receiving her Bachelor of Fine Arts from NYU's Tisch school in just three years.

Upon graduating she appeared in various off-broadway theater productions, had a stint singing in a dive piano bar and curated a performance/poetry series at the original Knitting Factory.

She and Bloedow recorded La Mar Enfortuna for Zorn's Tzadik label, featuring renditions of Sephardic and Ladino songs.

Charles was back on stage in 2008 in the Off Broadway production "Lightning at Our Feet", inspired by poet Emily Dickinson, under the direction of Obie winner Bob McGrath, with film maker Bill Morrison and composer Michael Gordon, which was part of the Next Wave festival at Brooklyn Academy of Music in December 2008, where she sang and acted, channeling the iconic 19th century poet.