Born on January 17, 1963, in Baltimore, MD; son of McDonald (a retired post office employee and church organist) and Flossie (a city social services worker and church choir director) Soulful jazz pianist Cyrus Chestnut might just be proof positive of the impact that music has on babies in the womb. Young Cyrus's home was filled with the sounds of the gospel music along with jazz records by artists such as Thelonius Monk and Jimmy Smith.
At age nine Chestnut was enrolled in the prep program at the Peabody Institute in Baltimore. He later headed to Berklee College of Music in Boston, where he earned a degree in jazz composition and arranging. Before graduating from Berklee in 1985, Chestnut had received the Eubie Blake fellowship in 1982, the Oscar Peterson scholarship in 1983, and the Quincy Jones scholarship in 1984. In his free time Chestnut studied the history of music and the work of such masters as pianists Bud Powell, Wynton Kelly, and Hank Jones, and the work of gospel artists Clara Ward, Charles Taylor, and Shirley Caesar. In school he studied classical music, writing and performing. A Warner Jazz website article on Chestnut quoted the New York Times, which described Chestnut as a "highly intelligent improviser with one of the surest senses of swing in jazz."
Chestnut went on to work with jazz vocalist Jon Hendricks from 1986-88, and trumpeter Terrence Blanchard and saxophonist Donald Harrison from 1988-90, before joining jazz legend Wynton Marsalis in 1991 famed vocal stylist Betty Carter. After a short stint playing aboard a Caribbean cruise ship in 1985 with a band that included Dizzy Gillespie, Joe Williams, and Tommy Flanagan. After Chestnut graduated from Berklee.
Chestnut has worked with an array of artists, including saxophonists James Carter, Donald Harrison and Joe Lovano; trumpeters Roy Hargrove and Freddie Hubbard; jazzman Chick Corea, the Chicago Symphony Orchestra, the Boston Pops, and opera singer Kathleen Battle, with whom he tours occasionally since 1995. More recently Chestnut has collaborated with vocalists Vanessa Williams, Anita Baker, Bette Midler, Isaac Hayes, and Brian McKnight. In 2000 he collaborated with Williams, McKnight and the Boys Choir of Harlem on an updated version of Vince Guaraldi's A Charlie Brown Christmas.
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 Jazz at Lincoln Center Orchestra, and the Dizzy Gillespie All-Star Big Band.