Miles quickly found his footing in the New York music scene, and though it took a little longer, he found Charlie Parker as well. “The first time I played [with Bird and Dizzy] I wasn’t great but I was playing my ass off in the style that I played, which was different from Dizzy’s, though I was influenced by his playing at this time. But people would watch for clues from Bird and Dizzy, and if they smiled when you finished playing, then that meant your playing was good.”
They did smile and Miles began to play with his heroes on a regular basis. When Diz was not there, Miles stepped in as the primary trumpet. He would play to the early morning then hustle back to morning classes at Juilliard. Photographs from this period show Miles dressed to impress, his still-skinny physique barely filling his sharp suits. To gain respect he forged a tough, street-wise persona. “Miles talks rough—you hear him use all kinds of rough words,” Gillespie told jazz historian Dan Morgenstern. “[But] his music reflects his true character… Miles is shy. He is super-shy. A lot of people don’t believe that, but I have know him for a long, long time.”
Miles familiarized himself with music theory, piano and dictation at Juilliard, and also learned the musical geography of the city: the modern jazz clubs were on 52nd Street, or simply “The Street”; in Harlem, a number of bars, like Minton’s, provided late-night opportunities to jam and be heard. It was at Minton’s that Bird introduced Miles to the house pianist, Thelonious Monk, whose harmonic innovations were codifying bebop. Monk’s use of space in his solos immediately influenced the young trumpeter; over time, their association would blossom and yield some of the most memorable music and historic moments of Miles’ career.
It was with Parker that Miles hung tightest and most often, even allowing the saxophonist to move into his apartment. In November 1945, Miles joined his idol in a studio just off Times Square to play on three of bebop’s most legendary recordings, Parker’s “Billie’s Bounce,” “Thrivin’ On A Riff” and “Now’s The Time.” On the last tune, as Bird completed his solo, Miles entered, tentatively at first, then with increasing confidence, improvising a statement that is markedly different from the high-register trumpet flurries of Gillespie and other bebop acolytes: bluesy, free of embellishment, economically phrased. The seed of the style that would take Miles to the top was sprouting.
Recording With Charlie Parker
Over the next few years, Miles would drop out of Juilliard (with his father’s blessing and his advice to his son to not imitate the sound of other musicians) and become a regular member of New York City’s modern jazz scene. He recorded often with Parker, enjoying the reflected glory of being in Parker’s band from a devoted jazz audience.
In 1947, Davis tied with Gillespie as top trumpeter in DownBeat’s critics poll, and his composition “Donna Lee” became a new bebop standard, which other bands recorded. His playing improved as he pushed himself night after night, and he released singles as a leader for the same label as Bird—the small independent Savoy Records out of Newark, New Jersey—and was often called in as a sideman by singers (Henry “Rubberlegs” Williams, Billy Eckstine, Ann Baker, Sarah Vaughan), composer/instrumentalists (Tadd Dameron, Charles Mingus, Benny Carter, Illinois Jacquet) and to add his name to celebrity lineups (Metronome All-Star Band, Birdland All Stars) that prove how his sound was developing and his star was ascending.
Drummer Roy Porter recalled Miles in an in-studio moment from 1946, revealing the young sideman’s burgeoning bandleader chops, helping to save Bird’s historic recording of “Night in Tunisia”: “Now on that break that Bird made, man, it was so hard for us to count it because we weren’t used to listening and everybody wasn’t coming in right. So Miles said ‘I tell you what, I’ll go over here by the piano, I’ll put my finger in my ear and on the first beat of the 17th bar when you’re supposed to come in, I’ll bring my hand down.’ That’s how it was made.”