When John Barr opened Nighttown on February 5, 1965, it was a one-room bar. Constructed in 1920, the building had previously housed the Cedar Hill Diner, a deli, Sam’s Beauty Parlor and Stock's Candies. The Silhouette Lounge, which was run by mob-operated Cadillac Amusements, replaced Stock's Candies in 1960. After the feds shut down the Silhouette Lounge, Barr leased the storefront and named the tavern after the Dublin red-light district in James Joyce’s Ulysses. The space was quite small and had an upright piano upon which a few local musicians would occasionally play. A restaurant area was added in 1966.
As Nighttown became more popular, Barr expanded the restaurant and bar into three other storefronts surrounding the original space. Today the 400-seat establishment comprises six dining rooms and three bars: the entire first floor of the three-story building. Barr sold Nighttown to Ireland-born Brendan Ring in 2001. As the building expanded (including a large covered patio named Stephen’s Green after Dublin, Ireland’s, best known city park) so did the list of guest performers. Barr had been a fan of stride piano, a type of jazz that was popular when the bar opened, but he only had space for one or two local players. When Brendan Ring became Nighttown’s general manager in 1993, he brought in Jim Wadsworth to book bigger national acts.
Nighttown now is one of the world’s premier venues for jazz music, according to DownBeat magazine. A short list of Nighttown’s performing alumni includes Freddy Cole, Jane Monheit, John Pizzarelli, Brian Auger, Ann Hampton Callaway, Tommy Tune, Ray Brown, Basia, Cyrille Aimee, Esperanza Spaulding, John Legend, Dick Cavett and Dick Gregory. In addition to formally booked acts, numerous musicians—from Wynton Marsalis to Stevie Wonder—have dropped in for impromptu performances. Nighttown also became the permanent home of the Press Club of Cleveland’s Journalism Hall of Fame in 2007.