Comedian Aries Spears recently opened up about a memorable skit he performed alongside Damon Wayans on the Showtime series *The Underground*. In the unscripted bit, Spears dressed as a mysterious character mistaken for a trans woman, a role he crafted off the cuff during a TSA security checkpoint scenario. Spears explained that the humor came from the ambiguity and mystery of his character, which kept Damon Wayans guessing and added to the comedy’s impact. Spears also clarified that his first time dressing as a woman on television was actually on *MADtv*, predating his famous *The Underground* and DMX mother sketches. Addressing criticisms about black men in drag, Spears embraced the comedic value of such roles, dismissing negativity and celebrating the laughter these performances inspired. His reflections highlight not only his versatility as a comedian but also conversations around gender and humor in black comedy culture.