The Five Spot, at 5 Cooper Square, the Bowery’s northern end, had begun its existence in the early 1900s as a dive called the Bowery Café, a small, nondescript bar among many other bars in the booming shadows of the Third Avenue El. The Bowery itself, all four‑fifths of a mile of it, had started out innocently back in Manhattan’s Arcadian days, as a country lane lined with small farms (the word “bowery” comes from an old Dutch word for farm); it wasn’t until the mid‑nineteenth century that the avenue began to go to seed, sprouting saloons, flophouses, whorehouses, tattoo parlors, greasy spoons, cheap clothing stores, and, of course, the bums whose very existence turned the thoroughfare’s name into a synonym for dereliction. The El went up in 1878, locking in the ambient shadiness.
Salvatore Termini, Joe and Iggy’s father, had bought the café in 1937, and when the two brothers came home from the war in 1946, they helped him run it. The clientele mainly consisted of drunks and blue‑collar workers: the booze was cheap, overhead was low, and so were profits, but it gave the Terminis a steady income. When Sal retired in 1951, Joe and Iggy took over. Then, in 1955, the El was demolished, and everything changed.
There had been outcries to clean up the Bowery ever since it first got dirty, and with the return of sunlight, the disinfecting began. The city widened and repaved the avenue, planted trees, installed streetlights, razed flophouses. Downtown artists and musicians, always on the lookout for cheap apartments and loft space, took notice and started to move into the neighborhood. When some of the new denizens of what was now being called the East Village began to drift in for a drink—or a seventy‑ five‑cent pitcher of beer at a poetry reading—Joe and Iggy Termini took notice. They spiffed up the place, put some art posters on the walls. A merchant marine and would‑be jazz pianist named Don Shoemaker held jam sessions in his loft next door: when running schooners of brew up and down the stairs got old, he suggested that the Terminis get a piano—the musicians could play right in the bar. It made business sense. The brothers bought an old upright and applied for a cabaret license. “They received the license August 30, 1956, and a week later opened for business as the Five Spot, the newest jazz club in the Village,” Robin Kelley writes. “Within weeks of the club’s reincarnation, the Five Spot earned a reputation as the local place for cheap beer and good music.”
Downtown types loved to drink, smoke reefer, and gossip: news traveled fast on the bongo‑drum grapevine. Soon the little place (official seat‑ ing capacity: seventy‑six) was awash in painters and sculptors—names that have solid‑gold Sotheby resonance in today’s commoditized world, but were then mainly known to gallery goers and each other: Willem de Kooning, Grace Hartigan, Franz Kline, Joan Mitchell, Larry Rivers, Bob Thompson, Jack Tworkov—and writers: Jack Kerouac, Gregory Corso, James Baldwin, Allen Ginsberg, Ted Joans, LeRoi Jones, Frank O’Hara. And then, musicians.
The jazz musicians arrived more gradually, because the core of jazz energy was Black, and Black faces were unwelcome in what was still a largely ethnic (Italian and Polish and Ukrainian) blue‑collar neighborhood. Ted Joans carried “a blackjack and a napkin filled with hot pepper to throw in their eyes in case I was attacked.” LeRoi Jones had a similar strategy, carrying “a lead pipe in a manila envelope, the envelope under my arm like a good messenger, not intimidated but nevertheless ready.”
The venturesome composer, arranger, and multi‑instrumentalist David Amram, then studying at Manhattan School of Music under Dimitri Mitropoulos, Vittorio Giannini, and Gunther Schuller, quickly found his way to the Five Spot and soon started hipping his music friends, many of them Black, to the place. One was a twenty‑seven‑year‑old pianist who seemed as far as possible from what the Five Spot’s white habitués might have expected of a jazz musician. Cecil Taylor came from an intellectual middle‑class family on Long Island; he was classically trained; he wrote poetry and read widely. (He also happened to be gay, though that was something no one talked about in those days.) And he played like nobody else. Taylor’s version of Thelonious Monk and Denzil Best’s “Bemsha Swing” took Monk’s version—which had already sounded radical to jazz audiences when Monk first played it in 1952—and cranked its cubism a few notches forward, sometimes commenting recognizably on the tune’s original lines, sometimes veering into glittering, dissonant, abstract‑ expressionist excursions. The poets and painters jammed shoulder to shoulder at the saloon’s tiny tables took note. By the winter of 1956–57—move over, Vanguard and Bohemia—the Five Spot had become the white‑hot center of experimental jazz in New York.
The spring of ’57 brought the club national fame: the Magnum photographer Burt Glinn shot a photo spread there for Esquire; Steve Allen ran a short, respectful segment on it on The Tonight Show. The same period also saw the ascension of Thelonious Monk. On Thursday, July 4, he began his eight‑week stand at the Five Spot with two ad hoc sidemen, bassist Michael Mattos and drummer Mack Simpkins, the musicians he wanted not being immediately available. But on July 16 he had his own band in place: Wilbur Ware, the drummer Frankie Dunlop, and, in fulfillment of Monk’s promise, John Coltrane.
Word quickly got out that something extraordinary was happening at the Five Spot. On weekend nights that summer, long lines formed in the soft dusk. Eight weeks turned into sixteen, and then into almost six months. The long stand became historic by every measure, even while it was happening. If you loved jazz, you had to be there—and many, including many fellow musicians, returned again and again. Bud Powell is said to have attended four nights in a row. J. J. Johnson went just once, but later said, “Since Charlie Parker, the most electrifying sound that I’ve heard in contemporary jazz was Coltrane playing with Monk at the Five Spot I had never heard that kind of performance—it’s not possible to put into words. I just heard something that I’ve never heard before and I haven’t heard since.” The critic François Postif, who frequented the club during the period, predicted Coltrane’s impact on current jazz musicians would be “as great as that of Charlie Parker.”
Coltrane had shifted into a new gear. A good part of his transformation had to do with a brand‑new commitment to clean living. “About that time I made a decision,” he told August Blume. “That’s when I stopped drinking and all that shit. I was able to play better right then, you know. . . . I could play better and think better, everything. And his music, that was a stimulant.” He laughed.
Coltrane was referring to the Monk‑ness of Monk, the quantity that
seemed at first like sheer musical unpredictability. Miles, as we’ve seen, grappled with it, unsuccessfully at first (though a good part of their early clashes, music‑based as they were, would also have had something to do with the antler‑locking of two alpha‑male geniuses). For unfledged ac‑ companists, Monk could be terrifying. His inner metronome gave no clear rhythmic cues, and his spare, jagged chords pointed in no obvious musical direction: those who played with him not only had to learn the unconventional structures of his compositions, but also how to let go and enter Monk‑mind, forging new neural pathways in their musical brains.
“Opening night he was struggling with all the tunes,” LeRoi Jones wrote of Coltrane. But, Lewis Porter writes, the saxophonist “went through a transformation during the engagement. Monk’s compositions challenged Coltrane’s knowledge of harmonic progressions, his spare and percussive accompaniment gave Coltrane a new‑found freedom, and his motivically structured improvisations served as models from which Col‑ trane could learn.”
And then there was the dancing. If the music was swinging and Monk’s spirits were high—as they often were over the six months of the Five Spot stand—he began doing something he’d never done before in performance: get up from the piano bench while one or another of his players soloed and go into a little shuffle‑tap, circling, eyes closed, returning to the keyboard at whatever moment he deemed right.
Monk’s dancing was also of a piece with another custom of his at the Five Spot: “From time to time,” Coltrane told Postif, “Monk went off to have a drink and left us alone, Wilbur Ware, Shadow Wilson and me. . . . And we improvised without any constraints for fifteen or twenty minutes, exploring our different instruments like madmen.”
The pianist might even retire to the dressing room and stare out the window for a while—maybe a long while—still in the music in his head but in effect creating a different kind of solo, a Cage‑ian silence.
“He said he wanted to hear us, he said he wanted to hear the band,” Coltrane said. “When he did that, he was in the audience himself, and he was listening to the band. Then he’d come back, you know, he got some‑ thing out of that thing, man.”
Monk’s wandering ways could be unsettling to his players at first. “I felt a little lonesome up there,” Coltrane told Blume, laughing. Suddenly he had all the room in the world to solo, but what would he play over a period that, depending on Monk’s mood, might last an hour or more? Everything, Coltrane said, depended on his spontaneous interaction with the bassist—and while Ware was there, there was another set of challenges. “A bass player like Wilbur Ware, he’s so inventive,” he said.
Like, he doesn’t always play the dominant notes Wilbur, he plays
the other way sometimes. He plays things that are kind of, you know, they’re foreign. If you didn’t know the song, you wouldn’t be able to find it. [chuckles] Because he’s superimposing things. He’s playing around, and under, and over—building tension, so when he comes back to it you feel everything suck in. But usually I knew the tunes—I knew the changes anyway. So we managed to come out at the end together anyway. [laughs] A lot of fun playing that way, though.
Wallace Roney described Coltrane’s playing by contrasting it with that of the great, bluesy alto player Lou Donaldson: “If you heard Lou Donaldson— who played beautiful—you heard the chord, and you heard notes that fit right in the chord.” Roney vocalized a demonstration. “When you heard Coltrane you heard”—here he sang a much wilder Coltrane run—“but it sounds right,” he said. “It sounds like something that’s taking the music— not out, but to the future, you know what I mean? He’s playing the extensions of the chords. And he’s playing out on the fringes of the chords.”
Miles Davis, working across town at Café Bohemia with a new quintet—Sonny Rollins, Red Garland, Paul Chambers, and Art Taylor— quickly got wind of what was happening at the Five Spot. As Roney re‑ membered, “He said someone would come up to him and say, ‘Man! You hear Trane with Monk? Man, that’s amazing!’ And Miles would say, ‘I know how Trane play! I was telling you Trane was bad before all that—’ And the person would say, ‘No, Miles, this is even different.’ And then someone else would come back and say, ‘Have you heard Monk and Trane?’
“So Miles said he went down there to the Five Spot. He said, man, he walked in and Trane was in the middle of one of his solos, and Monk was off the piano just dancin’, and Trane”—Roney imitated another wild Trane solo—“and Miles said, ‘Man, I found myself down there every night—late for my gig!’”
Excerpted from 3 SHADES OF BLUE: Miles Davis, John Coltrane, Bill Evans, and the Lost Empire of Cool by James Kaplan. Used with the permission of the publisher, Penguin Press, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2024 by James Kaplan.
