On January 6, 1950, The Gay 90s moved downtown to Plankinton Avenue, where owner Gordy Tobin transformed it into a show lounge. Tobin was so committed to quality that he would only hire performers aged 50+ who could actually recreate the stage style of the 1890s. Former customers remember the Gay 90s for its theatrical, circus-like atmosphere, which attracted flamboyant, thrill-seeking crowds. The Gay 90s offered showtunes singalongs, drag shows, comedians, and other nostalgic vaudeville traditions.

When Tobin retired in August 1954, the business moved to Michigan Street under the ownershop of "Baron" Milton Siegel.