Tootsie's Orchid Lounge

Tootsie's Orchid Lounge has occupied 422 Broadway since 1960, when Hattie Louise "Tootsie" Bess took over a struggling honky-tonk and painted it a shade of purple that has never left. The key fact of its geography is a back door that opens onto the alley running directly behind the Ryman Auditorium, fifty yards away. Grand Ole Opry performers who slipped out during intermission found themselves at Tootsie's. The bar became, by proximity and reputation, the unofficial green room of the Opry — a place where the famous and the aspiring drank side by side.

In the early 1960s the clientele included Waylon Jennings — not yet the outlaw, but a young singer chafing against Nashville's demand that he smooth his sound into something easier to sell. Kris Kristofferson was working as a janitor at Columbia Studios on Music Row, trying to get anyone to listen to his songs; Tootsie's was where he spent his evenings, and it was reportedly here that Roger Miller first heard "Me and Bobby McGee" and told him to keep going. Willie Nelson was another regular in his Nashville years before his reinvention in Texas. The bar served as waiting room, rehearsal space, and consolation for a generation of country musicians who were either not yet famous or no longer quite famous enough.

Tootsie herself kept a hatpin in her beehive for managing difficult customers and extended credit tabs to broke musicians for years, sometimes feeding them for free. She died in 1978. The bar has been in continuous operation under changing ownership ever since, still purple, still on Broadway, with the alley door behind the Ryman still there for anyone who needs it.