[1][3] After struggling at Fauquier High School while balancing schoolwork with farmwork and caring for his grandparents, he managed to graduate in 1974, though he was not able to attend college due to his family's financial situation.

After initially taking the stage under the name Sharyn O'Brien, someone suggested that "you need an African American name.

"[1][3][6][7] She was a key member of the Academy of Washington, a now-shuttered social club for drag performers, and won various awards from the organization before it closed in 2015.

There, she hosted the long-running Ladies of Illusion show on weekends until the nightclub's closure during the 2020 COVID-19 pandemic.

[1][3][6][9] Fitzgerald, who created the show, served as director, emcee, and performer, and became one of the club's best-known acts, sometimes referred to as the "First Lady of Ziegfeld's.