Individual | Inducted 2026
Maya Douglas began her career in the pageant and performance world through the Miss Continental Pageant, to which she traveled from Rochester, New York, in 1984. On her second attempt, she won the Miss Continental title in 1985 at age 23. Encouraged by Shante’, known as Alexandra Billings, Douglas moved to Chicago in 1987 and began performing at the Baton Show Lounge.
At the Baton, Douglas quickly became an audience favorite, appearing in three shows a night, five nights a week. She also created outfits and costumes for cast production numbers, work that enabled her to travel and perform nationally. Over the following decade, she contributed her time and skills to the Baton’s fundraisers and benefits, assisting with makeup, hair, and costuming. She formed close friendships with Ginger Grant and Chilli Pepper and later spoke at both of their funerals.
Douglas began her transition in 1987. During her career, she won Miss Gay USofA in 1995, National Entertainer of the Year in 1997, Universal Show Queen in 1999, and Miss Continental Elite in 2006, completing a return to the pageant system where her career had begun. She judged Miss Gay USofA for nine years beginning in 1997 and has more recently served as a regular judge for the Continental system for seven years.
As an established performer, Douglas became a mentor to many emerging entertainers, offering guidance, advice, and creative criticism. She credits performers including Leslie Rejeanne’, Dina Jacobs, and Chilli Pepper with providing her own formative guidance. She also appeared on the television programs *Jerry Springer*, *Sally Jessy Raphael*, and *Maury Povich*, bringing drag and trans performance to national audiences. Her work is included in the picture books *D.R.A.G.* and *Legends of Drag*.
Since 2008, Douglas has provided hair and makeup services for “Dance Divas,” a fundraiser for the Chicago Dance Heath Fund. She has donated her time and talent to the event every year since, supporting fundraising for financial and medical assistance. Douglas has called Chicago home since 1987 and has worked as an entertainer for more than four decades.