The Five Spot had been a neighborhood bar, but started featuring jazz at the suggestion of painters and poets who had been moving into nearby lofts since the 1940's. It quickly made a splash on the New York music scene with a long residency by Thelonious Monk in 1957. Monk's seven month stint at the club was a landmark for both the artist and the club. It was the first time he had performed in a New York club since losing his New York City Cabaret Card in 1951. He was backed by John Coltrane on tenor sax, Wilbur Ware on bass (later replaced by Ahmed Abdul-Malik), and Shadow Wilson on drums. The triumphant stay at the Five Spot was a major step in America's recognition of Monk's genius. It also made the Five Spot the East Village's premier jazz club. Monk would return to the club for many engagements in subsequent years.
Another groundbreaking event occurred in November 1959 when Ornette Coleman brought his pianoless quartet featuring Don Cherry on cornet, Charlie Haden on bass, and drummer Billy Higgins to the Five Spot. His six-week stay at the club shook the jazz world.
Many other jazz greats performed at the club, and many live recordings have been released over the years, including: Thelonious Monk's two albums with Johnny Griffin, Thelonious in Action and Misterioso; Monk's reunion with John Coltrane Discovery! Live at the Five Spot (all from 1958); Eric Dolphy's quintet with Booker Little on At the Five Spot volumes 1 and 2 and Memorial Album (1961); Pepper Adams' 10 to 4 at the Five-Spot and Charles McPherson's Live at the Five Spot.
Williams, Martin. "A Night at the Five Spot," Downbeat, February 13, 1964.