A small basement in Manhattan's Greenwich Village neighborhood, an area known for its bohemian values, is home to what is now one of jazz's oldest and most significant venues, the Village Vanguard. Although its very name, geography, and twentieth-century countercultural context define the Village Vanguard, a haven for experiment, its unequaled historical significance and current status as a major landmark within worldwide jazz culture have led to a twenty-first-century reality in which the club not only features but also plays an important role in defining the music that constitutes the most widely accepted subgenre of contemporary jazz, an improvisatory, small-group tradition rooted in the philosophical and musical heritage of bebop. Through an examination of performances both at the Vanguard and in other contexts by pianist Fred Hersch, a performer regularly featured at the club, this article argues that the cultural role of the Village Vanguard, both in spite of and because of the way its longtime owner Lorraine Gordon retained mid-twentieth-century appearances and practices, has shifted from its former purpose as a space for avant-garde experiments to become a powerful force in defining mainstream jazz. Hersch tailors his performances to suit the culture of the Vanguard at multiple levels, including his choice of personnel and ensemble type, the repertoire he does and does not play there, and the musical details of his improvisatory practices. Due to the venue's fame and prevalence as a recording space, choices like these by Hersch and other musicians shape the music widely understood to be at the center of the “jazz tradition,” marking a shift in the nature of the Vanguard that parallels changes in both its local and global context over the past half century as Greenwich Village has undergone substantial gentrification and jazz has gained an ever-stronger foothold as an institutionally recognized art music.