Bill's Place

Bring your own booze to Bill's Place. The owners don't mind. In fact, they encourage it, as this Harlem hole-in-the-wall (or, more accurately for the basement location, hole-in-the-ground) doesn't serve liquor. That's because, since opening in 2006, Bill's has been one of New York City's most authentic jazz speakeasies, evoking a bygone era when Prohibition bred creative booze, and even more creative music.

While Bill's Place is relatively new, it's located on the strip of 133rd Street between Lenox and Seventh Avenues historically known as "Swing Street." Brimming with illicit basement joints serving hot music and cool "bathtub gin," Swing Street is where jazz greats such as Billie Holiday got their start in the 1930s.

By the end of the decade, with Prohibition long gone and racial tensions overtaking the city, Swing Street lost much of its light, and by the time Bill's Place owners Bill Saxton and Theda Palmer Saxton found 148 West 133rd Street, the block had become placidly residential. While Bill Saxton is a Harlem native and celebrated saxophonist, he didn't know the full extent of Swing Street's history when the couple first purchased the spot. Yet, say the Saxtons, some shadow of bebop energy—a vibe, if you will—lived on in the building. It was only later that a neighbor pasted an article to their door, detailing their block's historic clout. The couple later discovered that their address had once been home to Tillie's, a jazz joint as famous for music as for fried chicken, and then Monette's Supper Club, where Billie Holiday is rumored to have been discovered by a record producer.

Following in these famous footsteps, Bill's Place's iconic red awning is now a beacon to jazz lovers from New York and beyond. Historically, Swing Street was a space where races and genders could mix far more freely than in the largely-segregated city, Leslie Pariseau writes in Punch. Bill's Place continues that legacy, with a diverse mix of locals and tourists crowding into the tiny basement cubbyhole to be transported by the jazz. And who knows: If you go to Bill's Place on a Friday night and pay close attention, you just might see the ghost of a young Billie Holiday alongside the musicians.