Cyrus Chestnut balances his lithe technical skill with a robust, soulful style that speaks to his deep gospel roots and love of swinging hard bop. Having grown up playing in the church, Chestnut learned early on how to infuse his swinging, classically trained style with a warm gospel sound. It was a style he perfected in the late '80s and early '90s as a sideman, backing legendary vocalists Jon Hendricks and Betty Carter, as well as with instrumentalists like Donald Harrison and Wynton Marsalis. As a leader of his own groups, he has collaborated with well-respected rhythm section players including Christian McBride, Carl Allen, Clarence Penn, Ron Carter, Lewis Nash, and others. Often working in a trio, as on 2016's Natural Essence with Buster Williams and Lenny White, or with guest artists as on 2001's Soul Food, he displays his virtuosic skill and mastery of the jazz tradition.
Chestnut first started playing piano at age three, and by age five was already performing at the Mount Calvary Baptist Church, which he attended with his parents. By age nine, he was studying classical piano in the prep program at the Peabody Institute. All the while, he continued to develop his gospel and jazz skills, and in 1981 enrolled at Boston's Berklee College of Music, where he earned his degree in jazz composition and arranging. While there, he earned the Eubie Blake Fellowship, the Quincy Jones Scholarship, and the Oscar Peterson Scholarship. After graduating, he found himself an in-demand sideman, working throughout the late '80s and early '90s with a string of well-known performers including Jon Hendricks, Wynton Marsalis, Terence Blanchard, Donald Harrison, and others. However, it was his early association with vocalist Betty Carter, with whom he toured and recorded, appearing on 1992's It's Not About the Melody, that had a lasting influence on the pianist. Purportedly, Carter encouraged Chestnut to push himself to be more individualistic by taking chances and trying to surprise her.
Chestnut took his time to develop, and made his solo debut in 1992 with The Nutman Speaks and Nut. Recorded for Japan's Alfa Jazz label, the albums showcased the pianist's trio with bassist Christian McBride and drummer Carl Allen. A third trio effort with McBride and Allen, Another Direction, followed on Evidence in 1993. Chestnut then signed with Atlantic and issued 1994's Revelation with bassist Christopher J. Tomas and drummer Clarence Penn. Several more highly regarded Atlantic releases followed, including 1995's Earth Stories and 1998's Cyrus Chestnut, which featured guest spots from Joe Lovano, James Carter, and Anita Baker. Also during this period, he appeared on vocalist Madeleine Peyroux's Dreamland, and collaborated on projects with other artists including Tim Warfield, Kathleen Battle, James Carter, Dee Dee Bridgewater, Rodney Whitaker, and more. He also made his acting debut, performing as a character based on Count Basie in director Robert Altman's 1995 film Kansas City.
Chestnut delivered his first holiday-themed album, Charlie Brown Christmas, which hit number three on the Billboard Jazz Albums chart. He then rounded out his Atlantic contract with 2001's all-original Soul Food, a exuberant set featuring appearances by Marcus Printup, James Carter, Gary Bartz, and others. He then moved to Warner Bros. for 2003's trio effort You Are My Sunshine, with bassist Michael Hawkins and drummer Neal Smith. He then expanded the same group to a quartet, adding guitarist Russell Malone on 2006's Genuine Chestnut. A year later, he applied his urbane jazz chops to the music of Elvis Presley on Cyrus Plays Elvis, followed by 2008's modal jazz-leaning Black Nile on Japan's M&I label. In 2013, he delivered the hard bop-infused Soul Brother Cool, which featured trumpeter Freddie Hendrix. He then showcased his trio on the 2014 concert album Midnight Melodies, recorded live at Smoke in New York City. Also in 2014, he joined Jimmy Greene on the saxophonist's poignant, Grammy-nominated album Beautiful Life.
Chestnut then moved to HighNote, debuting for the label with the 2015 trio effort A Million Colors in Your Mind, with bassist David Williams and drummer Victor Lewis. For his second HighNote effort, 2016's Natural Essence, the pianist was joined by the veteran rhythm section of bassist Buster Williams and drummer Lenny White. Williams and White were also on board for 2017's There's a Sweet Sweet Spirit, which also featured vibraphonist Steve Nelson. Also that year, he paired with Charnett Moffett on the bassist's Music from Our Soul. In 2018, Chestnut returned with Kaleidoscope, a classical-influenced trio album featuring bassist Eric Wheeler and drummer Chris Beck. Included on the album were jazz reworkings of compositions by Wolfgang Amadeus Mozart, Claude Debussy, Erik Satie, and more.