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Garland began his musical career studying clarinet and alto saxophone under the tutelage of Buster "Prof" Smith, who had previously been an early mentor of saxophonist Charlie Parker. Having been drafted into the army in 1941, Garland began to learn piano whilst stationed Fort Huachuca, Arizona, practicing relentlessly until his playing quickly became proficient. It was also around this time that Garland undertook a short-lived amateur boxing career, racking up 35 professional fights in total which would include facing a young Sugar Ray Robinson in the ring, although he would go on to lose this particular bout. Fortunately, his time spent as a welterweight seemed to have no negative impact on his performance, and after being discharged from the army in 1944 he immediately began playing small venues all over Texas. By the turn of the 1950s, Garland's stature as a musician had increased incalculably, having performed with a plethora of jazz greats including Coleman Hawkins, Lester Young, Ben Webster and Sonny Stitt, as well as leading his own trio. Garland embarked on without a doubt his most famous collaboration in 1955 when he was invited to join Miles Davis' band, which at the time also featured Coltrane, Philly Joe Jones and Paul Chambers. Garland would remain in Davis' band until the summer of 1958, recording such classic albums as Miles: The New Miles Davis Quintet, 'Round About Midnight and Milestones. Quite astoundingly, Garland would somehow also manage to produce numerous highly-regarded albums of his own during this period. Following his debut A Garland Of Red, he went on to record such classics as John Coltrane With The Red Garland Trio, further building on his previous work with the renowned saxophonist, and All Mornin' Long, with critic Ira Gitler describing the epic 20 minute title track as a "many-splendored, deep-dish demonstration of feeling, mood and melody."

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