Born in 1963, Chestnut started his musical career at the age of three, playing piano at the Mount Calvary Star Baptist Church at the age of six in his hometown of Baltimore, MD. By age nine, he was studying classical music at the Peabody Preparatory Institute inBaltimore. In the fall of 1981, Cyrus began jazz education in Boston, MA at the Berklee College of Music. In 1985, he earned a degree in jazz composition and arranging. While at Berklee, Chestnut was awarded the Eubie Blake Fellowship, the Oscar Peterson, Quincy Jones, and Count Basie awards for exceptional performance standards at the college. After Berklee, Cyrus began further honing his craft as a sideman with some of the legendary and leading musicians in the business. Some of these great people include; Jon Hendricks, Michael Carvin, Donald Harrison, Terence Blanchard, Wynton Marsalis, Branford Marsalis, Delfeayo Marsalis, Freddie Hubbard, Benny Golson, Curtis Fuller, Regina Cater, Chick Corea, Jimmy Heath, James Moody, Joe Williams, Isaac Hayes, Kathleen Battle, Betty Carter, and Dizzy Gillespie just to name a few. His association with Betty Carter, which began in 1991 significantly affected his outlook and approach to music, confirming his already iconoclastic instincts. Carter advised him to “take chances” and play things I’ve never heard,” Chestnut says.
As Cyrus was absorbing experiences as a sideman, he was also developing as a leader, recording and playing live around the world. There’s a Brighter Day Coming was his first self-released album, followed by The Nutman Speaks (1992), The Nutman Speaks Again (1992), Another Direction (1993). The records received the prestigious Gold Disk award from Japan’s leading jazz publication, Swing Journal.
In the summer of 1993, Chestnut signed with Atlantic Records, releasing the critically acclaimed Revelation (1994), followed by The Dark Before The Dawn (1995), EarthStories (1996), Blessed Quietness (1996), and Cyrus Chestnut (which featured Anita Baker, James Carter, Joe Lovano, Ron Carter, Billy Higgins, and Lewis Nash, 1998). In 2000, Cyrus was given a great honor to pay tribute to his favorite cartoonist, CharlesSchulz and first jazz influence, Vince Guaraldi in his interpretation of the classic Charlie Brown Christmas, which celebrated Mr. Schulz’s 50th year of writing the saga of Charlie Brown. Vanessa Williams, Brian McKnight, The Manhattan Transfer and the Boys Choir of Harlem were a few of the participants on this star-studded record. In 2001, he released Soul Food, featuring bassist Christian McBride, drummer Lewis Nash, and special guest soloists including James Carter, Stefon Harris, Wycliffe Gordon, and Marcus Printup. This acclaimed record was included in Down Beat’s list of the best records of 2001 and ascended to the “Top 10” on the Jazz charts. In 2005, Cyrus recorded "You Are My Sunshine” on the Warner Jazz label. This record was and still is a hit with jazz and gospel lovers alike. It featured Neal Smith on drums and Michael Hawkins on bass.
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