“[Thelonious Monk] played each note as though astonished by the previous one, as though every touch of his fingers on the keyboard was correcting an error and this touch in turn became an error to be corrected and so the tune never quite ended up the way it was meant to. Sometimes the song seemed to have turned inside out or to have been constructed entirely from mistakes. His hands were like two racquetball players trying to wrong-foot each other; he was always wrong-fingering himself. But a logic was operating, a logic unique to Monk: if you always played the least expected note a form would emerge, a negative imprint of what was initially anticipated. You always felt that at the heart of the tune was a beautiful melody that had to come out back to front, the wrong way around. Listening to him was like watching someone fidget, you felt uncomfortable until you started doing it, too.
“Sometimes his hands paused and changed direction in midair. Like he was playing chess, picking up a piece, moving it over the board, hesitating and then executing a different move from the one intended—an audacious move, one that seemed to leave his whole defense in ruins while contributing nothing to his attacking strategy. Until you realize that he’d redefined the game: the idea was to force the other person to win—if you won you lost, if you lost you won. This wasn’t whimsical—if you could play like this then the ordinary game became simpler. He’d got bored with playing straight-ahead bebop chess.
“Or you can look at it another way. If Monk had built a bridge he’d have taken away the bits that are considered essential until all that was left were the decorative parts—but somehow he would have made the ornamentation absorb the strength of the supporting spars so it was like everything was built around what wasn’t there. It shouldn’t have held together but it did and the excitement came from the way that it looked like it might collapse at any moment just as Monk’s music always sounded like it might get wrapped up in itself.”
—Geoff Dyer, offering the best description of Thelonious Monk’s style that I’ve ever read, in But Beautiful: A Book about Jazz (1991)