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Sandra Caldwell (born 1952) is an American singer and actress. She is known for her extensive career in American and Canadian theater, film and television. Caldwell began her career in New York City as a showgirl and eventually settled in Toronto where she performed in various productions including Rocky Horror Show,  Leader of the Pack and Beehive. Caldwell also appeared in a variety of American television shows including Little Men (1998-1999), Soul Food (2001-2002) and miniseries The Book of Negros (2015). In 2016, Caldwell was cast as Mama Darleena Andrews, a transgender woman who runs an LGBTQ etiquette class for Chicago youth, in MCC Theater’s production of Charm. Upon receiving this role, Caldwell publicly shared her experience as a transgender woman for the first time. Caldwell was featured in the Netflix documentary, Disclosure: Trans Lives on Screen (2020) to speak about her experience of “living in stealth” within the entertainment industry. She continues to speak about her identity and recently re-wrote her one-woman show, “The Guide to Being Fabulous After You Skinned Your Knee,”  to include her transition story.

Early Life
Caldwell was born in Washington, D.C. At the age of 13, she ran away to New York, where she continued to live for nine years. When she was 18, Caldwell bought a ticket to see Follies on Broadway and realized that she wanted to pursue performance as a career. During her time in New York, Caldwell was a member of the prominent ballroom family, House of LaBeija. However, she left the ballroom scene to pursue acting. While in New York, Caldwell performed as a showgirl. Eventually, she auditioned for a production of Beehive in the Imperial Room and subsequently moved to Toronto.

Theater
Caldwell performed in a variety of plays and musicals both in the United States and Canada. After leaving New York, Caldwell landed her first role in Beehive and subsequently performed in The Rocky Horror Show (1976) and Leader of the Pack. From 1990-1991, Caldwell performed as an Apollo singer in the Broadway Musical, Buddy: The Buddy Holly Story. In 1997, Caldwell was nominated for a Dora Mavor Moore Award for her role in Sophisticated Ladies. After this performance, Caldwell was featured in a U.S. production of Dreamgirls. In 2001, she acted in a production of Anne-Marie MacDonald’s, Anything that Moves at the Tarragon Theatre. The following year, Caldwell performed in the musical Dance of the Dead.

Caldwell also wrote and starred in a one-woman show, The Guide to Being Fabulous After You Skinned Your Knee, which she first performed at the Berkeley Street theater in Toronto. After coming out to her manager Alicia Jefferey in 2016, the women worked together to modify the show to include Caldwell’s transition story.

In 2016, Caldwell auditioned for the role of Mama Darlene in Philip Dawkin’s drama, Charm. This drama was based on the real-life figure, Miss Gloria Allen, a transgender woman who started an etiquette class for LGBTQ youth in Chicago. Following Caldwell’s casting in Charm, she publicly shared her experience as a trans-woman for the first time in a New York Times article. In 2017, Charm was performed off-broadway at the MCC Theater and included performances by Kelli Simpkins, Hailie Sahar, Marquise Vilson, Michael David Baldwin, Lauren F. Walker, Jojo Brown, Michael Lorz, Marky Irene Diven.

Film and Television
Caldwell also has an extensive career in film and television. Beginning in 1998, Caldwell had a small role in Maya Angelou’s film Down in the Delta. Following this role, Caldwell played Asia, a resident housekeeper, in the Canadian television show, Little Men (1998-1999) which was based on the book of the same name by Louisa Mary Alcott. The same year, she appeared in Canadian science fiction series, Mentors and the TV movie, Love Songs.

In 2001, Caldwell played a “public relations hack” to John Corbett’s character, Lars Hammond in Sernedipity. Additionally, Caldwell appeared as the president of an advertising company in ‘NSYNC’s film, On the Line. From 2001 to 2002, Caldwell had three guest appearances on the series Soul Food, the first hit drama that featured an African-American Cast in U.S. primetime television. In 2003, Caldwell had roles in a series of TV movies including Good Fences (2003) and The Cheetah Girls (2003). She was cast as one of the leads in Conan O’Brien’s TV pilot of Beat Cops, however, the show did not continue.

Caldwell had over fifty appearances as Georgia in the 2015 BET (US broadcast) and  CBC (Canadian broadcast) miniseries,  The Book of Negroes. In 2020, Caldwell was an interviewee and a creative consultant for the Netflix documentary, Disclosure: Trans Lives on Screen which was executively produced by Laverne Cox.