On February 29, 1940, the Oscars are set to make history in Hollywood, but the night takes an unexpected turn when Bartender Arthur Brooks, a hopeful Black filmmaker from rural Alabama, and his best friend Dottie Hudson, a disillusioned maid at the Ambassador Hotel, find themselves at a crossroads. As Academy Award Nominee Hattie McDaniel unexpectedly opts out of the night's grand event, Arthur and Dottie are thrust into a frantic mission to convince her to attend and seize her historic victory. This gripping play delves into themes of race, class, gender, and the shifting dynamics of Hollywood's golden age.