“I don’t think it came as easy with John [Gillespie] as it did for Bird,” mused Billy Eckstine, the honey-baritoned “Sepia Sinatra” who was Hines’s male vocalist (Sarah Vaughan handled the distaff chores). Could anybody have been cooler than “Mr. B.”? I don’t think so, not from the stitched edge of his softly rolled shirt collar to the crepe soles of his suede shoes. When Billy Eckstine left Hines at the beginning of 1944 to go out on his own, he hired Gillespie to put together what history would remember as the first bebop band. The first person Dizzy brought aboard was Charlie Parker. “Bird was responsible for the actual playing of it,” Eckstine explains, “and Dizzy put it down.” In To Be or Not to Bop, Gillespie says that “Charlie Parker was the other side of my heartbeat.”

MINTON’S UNIVERSITY OF BEBOP

Until Henry Minton took it over in 1938, the space was an unused dining room off the lobby of the Hotel Cecil. Standing at 118th Street between St. Nicholas and Seventh Avenues in Harlem, the Cecil housed many black musicians when they were in New York. Henry Minton was a saxophone player and a community leader, and the first African-American delegate to the American Federation of Musicians Local 802. In Shadow and Act, Ralph Ellison remembers Minton as someone you could always go to for a small loan, and a man who “loved to put a pot on the range.” It was Minton who transformed the Cecil’s old dining room’s battered bar, its discolored mirrors, and its postage-stamp dance floor into Minton’s Playhouse, a supper club with white linen tablecloths and flowers in little glass vases, a “first-class place,” Miles Davis told Quincy Troupe, “with a lot of style.”

Minton’s Playhouse functioned mainly as a hangout for Minton and his friends until the end of 1940, when Minton put Teddy Hill in charge of music. Although he’d fired him from a band the year before for “playing too modern,” Hill hired Kenny “Klook” Clarke to assemble a trio to back the club’s after-hours jam sessions. The first player that Klook—short for “klook-a-mop,” one of his trademark percussion figures—hired was piano player Thelonious Monk.

Thelonious Sphere Monk grew up on the Upper West Side of Manhattan, in a neighborhood, San Juan Hill, long since obliterated by Lincoln Center. The area’s name probably commemorates the First Negro Cavalry’s capture of the height above the Puerto Rican capital just ahead of Teddy Roosevelt’s Rough Riders during the Spanish-American War. San Juan Hill became the pre-Harlem heart of black New York after the denizens of the city’s first Little Africa were driven north from what is now Greenwich Village by razor-wielding Italian immigrants. Monk lived in the same fourth-floor walk-up apartment at 243 West Sixty-third Street for fifty years, first with his mother and sister after his dad moved back to North Carolina because of his asthma, then with Nellie Smith, the neighborhood girl who would become his wife and the mother of his two children.

Monk learned to play the piano by listening to his older sister, Marion, take lessons on the family’s old upright piano. When he was eleven the teacher figured out it was Thelonious who had the talent. Monk took lessons, but he soon figured out that no school was going to teach him to play like the musicians he loved—Duke Ellington, Fats Waller, and especially James P. Johnson, the great stride pianist who lived in the neighborhood when Monk was growing up. Monk began showing up every Wednesday for the Amateur Night contest at the Apollo Theater until he won so often that he was barred from the competition. By the time he was fourteen, he was playing at Harlem rent parties. Two years later, he quit high school to go on the road as a faith healer’s pianist.