Dorothy Jones, the quintessential renaissance woman of Jazz Age Harlem, operates an upscale dress shop by day and an exclusive, underworld speakeasy by night from her posh Sugar Hill brownstone. Unable to resist the request of her business associate and mentor, Johnny, Dorothy agrees to hostess an event at her speakeasy for the mob boss, welcoming a few new men into his organization. While sitting at the bar, Charlie, Dorothy's longtime friend and bartender, serves her hallucinogenic martinis made with Johnny's bootleg gin. After a few drinks, Dorothy awakes to find her speakeasy crash landed in the Land of Oz. Sporting her new ruby studded stilettos, provided courtesy of the deceased Witch of the East, Dorothy begins her journey along the Yellow Brick Road to the Emerald City, in hopes of meeting with the Wizard. However, Dorothy doesn't get very far in the five-inch stilettos, so she enlists the Scarecrow, Tin Man, and Lion, who are more than happy to assist Dorothy for reasons she can neither fathom nor conceive. For unbeknownst to Dorothy, once her stiletto heels click upon the Yellow Brick Road of the Emerald City, she will alter the future of Oz for all time.