Puerto Rican-American actress Holly Woodlawn was BOTD in 1946. Born in Juana Díaz, Puerto Rico, her family emigrated to the United States when she was a child, and she was raised in Miami. Assigned male at birth, she identified as transgender at a young age, adopting the name Holly in homage to the heroine of Truman Capote‘s novella Breakfast at Tiffany’s. At 15, she ran away from home, heading to New York City where she supported herself via sex work, experiences later referenced in Lou Reed’s song Walk On the Wild Side. She met artist Andy Warhol in 1968, becoming one of the “Superstars” of The Factory alongside Candy Darling. She starred in Warhol’s and Paul Morrissey’s experimental films Trash and Women in Revolt, reportedly spending her salary on heroin. Director George Cukor was so impressed with her performance in Trash that he lobbied for her to be nominated for the Best Actress Oscar. In 1971, she replaced Darling in a production of Vain Victory and was arrested later that year for impersonating the wife of the French Ambassador at the United Nations. After starring in Robert Kaplan’s underground film Scarecrow in a Garden of Cucumbers, she moved to San Francisco, where her career went into decline, but for a brief appearance in Rosa von Praunheim’s 1979 documentary Tally Brown, New York. Returning to New York in the 1980s, she became a cabaret performer. She had a brief career resurgence in the 1990s, appearing in Madonna’s music video Deeper and Deeper and the indie films Night Owl and Billy’s Hollywood Screen Kiss. She continued performing in cabaret into the 2000s, making her last screen apperance in Joey Soloway‘s trans-themed TV drama series Transparent. She died in 2015, aged 69. Her estate founded the Holly Woodlawn Memorial Fund for Transgender Youth in Los Angeles.