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.
In 2006, Chestnut made his Telarc debut with the release of Genuine Chestnut. The album is a carefully balanced mix of original material with some well-known pop melodies from the past several decades—all driven by Chestnut’s eclectic yet unmistakable jazz sensibility.
In addition to his regular backup unit of bassist Michael Hawkins and drummer Neal Smith, guitarist Russell Malone and percussionist Steve Kroon join Chestnut. The synergy between the regular trio lineup and the two guest players was a natural fit. "When you have that caliber of musicianship in the studio, getting comfortable is not a difficult task," says Chestnut. "I encouraged everyone to just be themselves. I brought Russell Malone into the studio to be Russell Malone. I brought Steve Kroon into the studio to be Steve Kroon. Likewise, Neal Smith and Michael Hawkins are there to do what they do best."
Cyrus has been featured on film playing a Count Basie inspired character in the Robert Altman film, Kansas City. 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 Dizzy Gillespie Alumni All Star Big Band, the Lincoln Center Jazz Orchestra, and the Carnegie Hall Jazz Orchestra. He has recorded with the people before mentioned and including Bette Midler, Freddy Cole, and many others too numerous to name.
Chestnut continually tours with his trio, playing live at jazz festivals around the world as well as clubs and concert halls. With his hectic schedule, Cyrus has also found the time to get into jazz education, doing seminars worldwide and also, on occasion, educating students in jazz at Middlebury College in Vermont during the winter months. Joined by bassist Dezron Douglass and drummer Neal Smith, he continually uses the trio format to extend, elaborate, and refine the basic conception of the jazz rhythm section. In his own words, "This country and this art form are founded on the basic principles of freedom, whereby a person is able to think, say, or play what he or she chooses. Throughout the years as I look at history, all of my predecessors, regardless of what environment was, shared freely their thoughts and feelings in a swinging, musical way on the bandstand.They swung hard and made the listeners feel better leaving than when they arrived. This is the tradition I intend to preserve."
The future is bright with great possibilities for Cyrus. Expect once again this year to hear a unique and unforgettable recording that only can come from someone like Cyrus Chestnut.