Schoolboy to Showgirl: The Alexandra Billings Story is a powerful documentary that chronicles the remarkable life of Alexandra Billings, a trailblazing transgender actress, singer, and teacher. Written and produced by Alexandra Silets, the film takes viewers on an intimate journey through Billings' multifaceted life, exploring her gender transition, battles with addiction, triumph over homelessness and HIV, and her ascent in the world of performance and activism. Part of the "Out & Proud in Chicago" series, the documentary premiered on PBS (WTTW-11) on June 19, 2009, and earned a nomination for an Emmy Award in the Best Documentary category. Through candid interviews and rare archival footage, the film offers a raw and deeply human portrait of one of the first openly transgender women to appear on American television.
Born in Illinois on March 28, 1962, Alexandra Scott Billings is of European American, African American, and Native American descent. Her father, Robert Billings, a music teacher and musical director, helped cultivate her early love for theater. She worked backstage with legends such as Carol Burnett and Yul Brynner and appeared in stage productions like Jesus Christ Superstar and The Roar of the Greasepaint, the Smell of the Crowd. In her early adult life, Billings faced intense personal struggles, homelessness, addiction to cocaine and opioids, and periods of sex work. Despite these hardships, she never lost her passion for performance and self-expression.
In the early 1980s, she found refuge and identity in the Chicago drag scene under the stage name Shanté. Performing at the famed Baton Show Lounge, she became known for her impersonations of Barbra Streisand, Judy Garland, and Liza Minnelli. Billings won numerous beauty contests, including titles like Miss Wisconsin, Miss New York, Miss Chicago, Miss Illinois, and Miss Florida. She also served as a judge for the Miss Continental pageant, a prestigious drag competition. Chicago theater became her creative haven, where she collaborated with noted playwrights such as Larry Kramer, Tina Landau, and Jamie Pachino.
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Billings earned a Joseph Jefferson Award and five After Dark Awards for her work onstage and toured nationally with her autobiographical one-woman show.
As a singer, she performed in cabarets and theaters across the country and recorded her second album, The Story Goes On, in 2003. In 2004, she was honored with the New York MAC Hanson Award for Cabaret Artist of the Year. Her Broadway presence came in full force in 2018 when she appeared in The Nap at Manhattan Theatre Club, marking one of the first times an openly trans actor was cast in a trans role on Broadway. In 2019, it was announced that she would join the cast of Wicked as Madame Morrible, becoming the first openly transgender person to play a major role in the musical. Following Broadway’s pandemic shutdown, Billings resumed the role in 2021, remaining with the production until early 2022.
Her television and film career is equally notable. In 2005, she starred in Romy and Michele: In the Beginning, playing one of TV's first openly transgender characters. She later appeared in Karen Sisco, ER, Eli Stone, Grey’s Anatomy, How to Get Away with Murder, and The Conners. Her portrayal of Davina in Amazon’s Transparent brought her widespread recognition as she played a central, emotionally resonant role in one of the most groundbreaking series of the 2010s.
In 2018, she joined the cast of Goliath and later appeared in the 2022 sci-fi series The Peripheral. In 2023, Billings starred in the Canadian film Queen Tut, earning a nomination for Best Lead Performance in a Comedy Film at the Canadian Screen Awards in 2024.
An educator as well as an entertainer, Billings has taught acting and performance methods at institutions including Lewis University, the University of Chicago, the University of Illinois, and the Steppenwolf School. She is currently a professor at the USC School of Dramatic Arts and previously taught at California State University, Long Beach, where she also earned her MFA and delivered the College of the Arts commencement address in 2015. Her teaching emphasizes not only craft but the importance of authenticity and voice.
Activism has always been at the heart of Billings’ public life. A longtime advocate for HIV awareness and LGBTQ+ rights, she has used her platform to challenge stigma, empower marginalized communities, and call for meaningful change. After receiving the Human Rights Campaign Visibility Award in 2016, she encouraged her audience to go beyond ceremony, urging them to actively engage in the fight for equality. In 2017, while accepting a GLAAD Media Award on behalf of the Transparent cast, she called upon the older generation of LGBTQ+ people to mentor the next, recognizing that the ongoing struggle for justice must be intergenerational.
Billings’ personal journey is deeply interwoven with her activism. She began her gender transition in 1980 and has been living with HIV since 1985.
Throughout the years, she has spoken openly about her experience with the virus and the essential support of her wife, Chrisanne, whom she met in high school drama class. The two held a commitment ceremony in 1995 and have remained devoted partners for decades. Billings attributes much of her resilience to Chrisanne’s unwavering presence during the darkest chapters of her life.
In 2022, she published her memoir This Time for Me, offering a candid, lyrical account of her life, losses, and triumphs. Through storytelling, teaching, performing, and advocating, Alexandra Billings has cemented her place as a pioneering figure in the entertainment industry and beyond. Schoolboy to Showgirl: The Alexandra Billings Story not only documents this extraordinary life but serves as a testament to the power of visibility, transformation, and unwavering courage in the face of adversity.
Image credits: pbs.org
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