The Vanguard began as something else entirely. Gordon was a literary man — he wanted a forum for poets and folk musicians, a Greenwich Village salon that happened to sell drinks. Through the 1930s and 1940s, Lead Belly played blues and folk music from the stage; Maxwell Bodenheim and Harry Kemp read poetry; the Duke of Iron brought Caribbean calypso. Jazz sessions crept in on Sunday afternoons, where the cover was fifty cents and the names onstage were Lester Young and Ben Webster. Lorraine Gordon, who would later marry Max and run the club for decades after his death, remembered that you could hear the greatest jazz musicians in the world for pocket change. Nobody called it the jazz club yet. That came later.

By 1957, Max Gordon had made a decision. Jazz went to the top of the bill. Folk acts and comedians would fill the gaps. Within months, the booking list read like a fantasy — Miles Davis, Thelonious Monk, Gerry Mulligan, Sonny Rollins, Bill Evans, Stan Getz, Carmen McRae, Charlie Mingus. The Monk booking was Lorraine's doing. She had met Max at a bakery on Fire Island and proposed that he give the relatively obscure pianist a week at the club. Max agreed. When Monk opened on September 14, 1948, nobody came — not the critics, not the cognoscenti, nobody. The Vanguard would eventually help make Monk's name. It took longer than a week.

What separates the Vanguard from other legendary jazz venues is the recordings. On November 3, 1957, Sonny Rollins recorded three LPs in one session in that triangular basement, laying the foundation for the piano-less trio and shaping the hard-bop movement. John Coltrane's Vanguard recordings from 1961 — five titles drawn from 22 songs over four nights — became some of the most studied documents in jazz history. Bill Evans recorded there so extensively that his Vanguard sessions constitute a small library; the last significant ones came just three months before his death in 1980. The phrase 'Live at the Village Vanguard' on an album cover became, as Blue Note Records president Bruce Lundvall once observed, a direct and positive influence on sales. The room's acoustics, the intimate pressure of those angled walls, pulled something out of musicians that they didn't always find elsewhere.

Max Gordon died on May 11, 1989. Lorraine closed the club for one day. The next day, she reopened it and ran it for nearly thirty more years. She died in June 2018 at age 95. The Thad Jones/Mel Lewis Orchestra — later the Vanguard Jazz Orchestra — had been playing Monday nights at the club since 1965, a residency that outlasted both of its founders. The club's calendar has barely paused since the 1930s. It remains, as one writer put it, a room with a life of its own: a wedge in the ground on a Greenwich Village corner where the history of jazz is still accumulating.