In 1993 Gilchrist formed the New Volcanoes, as a quartet that also contained trumpeter Freddie Dunn, bassist Vince Loving, and drummer Nate Reynolds. Trumpeter and sound engineer Mike Cerri was soon added, and Gilchrist recorded his first album, The Art Is Life, as a sextet with James Dephilipo added on euphonium. This was self-released, as was Gilchrist’s second album, Asphalt Revolt. He played with the New Volcanoes and gave solo performances on the East Coast for several years after graduating.

He first met Murray in 1999: Gilchrist introduced himself and later sent the saxophonist a recording of his playing. They played together a few weeks later, and the pianist joined Murray’s band after a few more weeks had passed. Their first gig together was at the Iridium Jazz Club in New York City in April 2000. Gilchrist subsequently obtained a recording contract with Hyena Records, but decided to remain in Baltimore, based on his belief that New York-based musicians tend to converge on a particular style of playing.

Gilchrist gradually built the sound of the New Volcanoes by adding particular musicians on different instruments, particularly Gabriel Ware on alto saxophone and Greg Thompkins on tenor. The latter commented that the pianist “does look at the horn section as a choir, […] But it’s a choir where anyone can get the spirit and take off”. The first release of original material on Hyena was 2005’s Towards the Shining Path, which received little attention, as Gilchrist did not have enough money to pay for the whole band to tour. To develop his reputation and capacity to tour, Gilchrist formed a more commercially viable band, a trio, with Anthony “Blue” Jenkins on bass and Reynolds on drums; they created the album Three.^[4]

Gilchrist’s 2008 New Volcanoes album Soul Progressin’ received a four-star review from Down Beat, which commented that “Gilchrist’s sanguine melodies, vulnerable and gospelized, distinguish the music from M-Base‘s cool austerity.” A 2012 recording of the same group also contained a mix of styles: one reviewer described one track from It Came from Baltimore: Live at the Windup Space Vol. 1 as containing elements of “Pop and the avant-garde, old and new, free-jazz and funk, hip-hop and rock, modernist dissonance and sentimental grooves”. Gilchrist also leads a trio called Inside Out, with Michael Formanek (bass) and Eric Kennedy (drums). Gilchrist’s New Urban World Blues was a musical re-telling of the 2015 Baltimore uprising that began with the death of a young African American man and is chronicled in the song “Blues for Freddie Gray”. A 4-volume set titled Compendium was released on Manta Ray Records in 2017.

His composition “Assume the Position” was used in the score for the HBO drama television series The Wire. His compositions have also been used in the HBO series Treme and The Deuce.