"Since the Montreal-born, long-US resident Bley's 50's debut with Mingus and Blakey, he's worked with more first-rate, wide ranging original musical minds than anyone but Miles..." —Howard Mandel, Downbeat, April 1995
Bley gave violin recitals at age five. By age seven he was studying piano. He went through numerous classical teachers—including one Frenchman that had him play, balancing filled water glasses on the tops of his hands. At age 11 he graduated from the McGill Conservatory—having taken on their musical curriculum in addition to his public school education. Bley, who was known as "Buzzy" in his early adolescence, formed a band and played clubs and summer hotel jobs in the Laurentian Mountains at age 13. Four years later he replaced Oscar Peterson at the Alberta Lounge. Bley founded the Montreal Jazz Workshop and brought Charlie Parker, Sonny Rollins, Brew Moore and Alan Eager to Montreal inorder to perform with them.
In 1950 Bley left for New York City. He studied at the Julliard School of Music from 1950-54. While at Julliard, Bley had a band with Jackie MacLean, Donald Byrd, Arthur Taylor, Doug Watkins. In this period he toured with Lester Young, Ben Webster, Roy Eldridge and Bill Harris. He was a frequent visitor at the famed Saturday night sessions at Lenny Tristano's studio. Bley served as president of the Associated Jazz Societies of New York in 1952, which led to Charlie Mingus hiring Bley to conduct his ensemble. Mingus also recorded Bley's debut album, along with himself and Art Blakey, on his label, Debut Records.
In 1957, Bley went to California where his bands included: Ornette Coleman, Don Cherry, Charlie Haden, Billy Higgens, Bobby Hutchinson, Scotty LaFaro, Lawrence Marable, and Dave Pike. In 1959 Bley returned to New York, where he played with Roland Kirk, Oliver Nelson, and Jimmy Giuffre at the Five Spot Cafe. This group evolved into the Jimmy Giuffre 3, including Bley and Steve Swallow, which brought Bley to Europe for the first time in 1961. They recorded for Verve and CBS.
In 1963 Bley and Herbie Hancock were invited to play with the bands of Miles Davis and Sonny Rollins, who were performing on a double bill on a Monday night at Birdland. Both pianists were offered both jobs. Hancock gave Bley first choice. Bley chose to join the Rollins quartet for a year to record and go to tour Japan. Bley's own trio with Gary Peacock and Paul Motian of the 1960's became the standard by which other trios would be measured.