A native of Baltimore, Maryland, Chestnut first studied piano with his father at the age of five, with official lessons beginning two years later. By the age of nine, he was enrolled in the prep program at the Peabody Institute. He graduated from Berklee with a degree in jazz composition and arranging. Chestnut took his time, working with a number of top-notch musicians (Jon Hendricks, Betty Carter, Terence Blanchard, and Donald Harrison) before finally recording his first solo CD at the age of 30. His initial dates as a leader were recorded for the Japanese label Alfa (reissued on Evidence), and he became an Atlantic artist in 1994. A self-titled LP followed in 1998, with Tribute to Duke Ellington following a year later.

In subsequent years, Chestnut remained busy, releasing Charlie Brown Christmas in 2000, the all-original Soul Food in 2001, You Are My Sunshine in 2003, Genuine Chestnut in 2006, and Cyrus Plays Elvis in 2007. The following year, he released 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 concert album Midnight Melodies, recorded live at Smoke in New York City. In 2015, Chestnut released his debut album for HighNote, the trio effort A Million Colors in Your Mind, which featured backing from bassist David Williams and drummer Victor Lewis. For his second HighNote effort, 2016's Natural Essence, the pianist was joined by bassist Buster Williams and drummer Lenny White. ~ Ken Dryden