Cyrus Chestnut was born in Baltimore, Maryland, in 1963. Chestnut started his musical career at the age of six, playing piano at Mount Calvary Baptist Church in his hometown. By the age of nine, he was studying classical music at the Peabody Institute. In 1985, Chestnut earned a degree in jazz composition and arranging from Boston's renowned Berklee College of Music. While at Berklee, Chestnut was awarded the Eubie Blake Fellowship (1982), the Quincy Jones Scholarship (1983), and the Oscar Peterson Scholarship (1984).
Chestnut toured as pianist for Jon Hendricks; Terrence Blanchard; Donald Harrison; Wynton Marsalis; and the Betty Carter Trio. His association with Carter significantly affected his outlook and approach to music, confirming his already iconoclastic instincts. Chestnut has also performed and/or recorded with, Freddy Cole, Bette Midler, Jon Hendricks,Freddie Hubbard, Jimmy Scott, Chick Corea, Isaac Hayes, Kevin Mahogany, Dizzy Gillespie, and opera diva Kathleen Battle, most notably on the Sony Classical recording "So Many Stars".
In 2006, Chestnut released his first album, Genuine Chestnut, on TelArc Records. Chestnut continually tours with his trio, playing live at jazz festivals around the world as well as clubs and concert halls. His leadership and prowess as a soloist has also led him to be a first call for the piano chair in many big bands including the Lincoln Center Jazz Orchestra, Dizzy Gillespie Big Band, and Carnegie Hall Jazz Orchestra. Chestnut is currently represented by Addeo Music International (AMI).