Profiles of Transgender Courage: Holly Woodlawn

Holly Woodlawn was a Puerto Rican transgender woman known for her work as an Andy Warhol Superstar. She was born in 1946 in Juana Diaz, Puerto Rico and grew up in Miami, Florida. She came out at a young age and adopted the name Holly after the heroine from the film Breakfast at Tiffany's and added the surname later after it appeared in an episode of I Love Lucy. She would tell people that she was the heiress of Woodlawn Cemetary, even though it wasn't true. In 1962, at the age of fifteen, she left Florida and made her way to New York. She recalled this experience in her memoirs, A Low Life in High Heels."I hocked some jewelry and ... made it all the way to Georgia, where the money ran out and ... had to hitchhike the rest of the way" to New York City. At the age of 16, when most kids were cramming for trigonometry exams, I was turning tricks, living off the streets and wondering when my next meal was coming." In 1969 she considered gender confirmation surgery but decided against it.

In 1968, Woodlawn met Andy Warhol at a screening of Flesh at his studio, The Factory. Warhol introduced her to Jackie Curtis, who cast Holly in her 1969 play Heaven Grand in Amber Orbit. That same October, she was cast in a small role in Warhol's film Trash. She impressed the director/screenwriter so much that he re-wrote the whole thing to give her a larger role. One year later, she received word that a petition was gathering support to nominate her for an Oscar for Best Actress for her work in Trash, though nothing ever came of this effort. In her next film Women in Revolt, another Warhol project, she joined other Warhol Superstars such as Candy Darling. In the film, she became one of the first people to use the word "cunt" in cinema.

Holly replaced Candy Darling in Vain Victory, another Jackie Curtis production in 1971. She spent some time in jail this same year in Puerto Rico and New York for shoplifting and impersonating the wife of the French Ambassador to the United Nations respectively. Initially, she was housed in a women's detention facility, but when her assigned sex at birth was discovered she was moved to a men's facility. In 1972, she appeared in a film called Scarecrow in a Garden of Cucumbers. It was a low budget film and unsuccessful musical feature. The film was conceived by Robert Kaplan and Paul Glickman, the premise was to use a transgender woman in the lead role without revealing the sex of the actress. In 1977, she moved to San Francisco but returned to New York later that year. In 1978 she was arrested and jailed for violating terms of probation and was released when politician Ethan Geto organized a benefit in her benefit appealing for her release. By 1979, her career was in a major slump and she returned to her parent's home in Miami.

Woodlawn moved back to New York in the mid-80's. She became a featured singer in Gabriel Rotello's Downtown Dukes and Divas Revue. She also starred in a variety of musicals. In 1991, she published her autobiography A Low Life in High Heels with writer Jeff Copeland. Throughout the 90's she experienced a mild theatrical comeback, making cameo appearances in films such as Night Owl in 1993 and Billy's Hollywood Screen Kiss in 1998. In 1999 she appeared in Controversial film Twin Falls Idaho, a film about conjoined twins living out of a hotel room in a small town. Woodlawn began performing in cabaret shows in sold-out New York and Los Angeles performances in the early 2000s. Most recently she appeared in Transparent, a show about a father who comes out as trans starring Jeffery Tambor.

After the death of Andy Warhol, she was frequently interviewed about her experiences with him. In the years before her own death, she made her home in West Hollywood, California where she participated in riot grrrl shows with Revolution Rising and recorded spoken-word for an experimental project by the band Lucid Nation. She became seriously ill in June of 2015 and was hospitalized at Cedars-Sinai Medical Center in Los Angeles. Tests showed that she had lesions on her brain and liver which were later determined to be cancer. She eventually moved into an assisted living facility where she eventually passed from brain and liver cancer on December 6, 2015. She was included in the In Memoriam segment of the 88th Academy Awards.