Holly Woodlawn was born as Haroldo Santiago Franceschi Rodriguez Danhakl in Juana Díaz, Puerto Rico, to an American soldier of German descent, and Aminta Rodriguez, a native Puerto Rican, and grew up in Miami Beach, where she came out at a young age. She adopted the name Holly from the heroine of Breakfast at Tiffany’s, and in 1969 added the surname from a sign she saw on an episode of I Love Lucy. After changing her name she began to tell people she was the heiress to Woodlawn Cemetery. In 1962, at the age of fifteen, Haroldo Woodlawn left Florida heading north, changing his name to Holly, after Audrey Hepburn’s character in Breakfast at Tiffany’s. She recollects that “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. Woodlawn met Andy Warhol at the Factory, at a screening of Flesh (1968). Through him she met Jackie Curtis, who cast Woodlawn in her play Heaven Grand in Amber Orbit in the autumn of 1969. In October, she was given a bit role in Trash, but so impressed director Paul Morrissey that she was given a much larger role. Warhol’s collaboration with Morrissey were always done on a shoestring budget. Joe Dallesandro was a heroin addict on a quest to score who, ambivalent about his sexuality meets transgender casual girlfriend, with a motherly figure in Holly’s role. Initially only a bit part in the dialogue, screenwriter Morrisey re-wrote it to give her the lead. The pair contrasted the other with violent episodes of over-dose matched by improvisation and sulky rejection. Woodlawn ad lib many of the lines herself, preferring creativity to strict adherence to the script. Woodlawn was paid $25 per day during filming, spending the last day’s on heroin. In October 1970, she received word from the Academy of Motion Picture Arts and Sciences that George Cukor, supported by others, was petitioning the Academy to nominate her for Best Actress for her work in Trash, however, nothing came of this campaign. In Morrisey’s next film she was joined by others in Warhol’s pantheon of stars, to play in Women in Revolt, a satirical look at the women’s rights movement and the PIGS (politically involved girls).

In May 1971, Woodlawn replaced Candy Darling at the La MaMa theatre in a production of Vain Victory written and directed by Jackie Curtis. She was arrested and briefly incarcerated in Puerto Rico after being caught shoplifting. Woodlawn created a stir when she was arrested in New York City after impersonating the wife of the French Ambassador to the United Nations. When arrested, she was taken to the Women’s House of Detention then transferred to a men’s facility when her assigned sex at birth was discovered. In 1972, director Robert Kaplan and cinematographer Paul Glickman concocted the idea of a movie whose premise would be using a transgender woman as the lead in a film without revealing the sex of the actress. Woodlawn played a young, starstruck girl hoping for success as an actress in New York City. The film, Scarecrow in a Garden of Cucumbers, was a low budget, 16mm, unsuccessful musical feature. The song “In The Very Last Row”, written by Marshall Barer, was performed by Bette Midler. In 1977, Woodlawn moved to San Francisco. She returned to New York later in the year, appearing on Geraldo Rivera’s talk show, before being jailed again in 1978 for violating terms of probation. She was released on the appeal of politician Ethan Geto, who helped organize a benefit for her. By 1979, she had surrendered to a faltering career, cut her hair and moved back to her parents’ home in Miami, while working as a busser at Benihana. Back in New York in the mid-1980s, she became a featured singer in Gabriel Rotello’s Downtown Dukes and Divas revues at clubs such as The Limelight and The Palladium, and a star of various musicals and revues mounted by the songwriting and producing team of Scott Wittman and Marc Shaiman. In 1991 she published her autobiography, the Holly Woodlawn Story, “A Low Life in High Heels” with writer Jeff Copeland.

During the 1990s, Woodlawn achieved a modest film and theatrical comeback, making cameo appearances in productions such as Night Owl (1993) and Billy’s Hollywood Screen Kiss (1998). After Warhol’s death, she was interviewed frequently on his life and influence. At the time of her death she resided in West Hollywood where in the late 90s she participated in riot grrrl shows with Revolution Rising, and recorded spoken words for songs with experimental recordings by the band Lucid Nation. In 1999 she was in a controversial film about conjoined twins who live in a run down motel in a small town. Twin Falls Idaho was followed four years later by Milwaukee, Minnesota. More recently she acted in Transparent a US TV series about a transgender father played by Jeffrey Tambor. Woodlawn fell seriously ill in June 2015, and was hospitalized at Cedars-Sinai Medical Center in Los Angeles, California. She was so weak that physicians feared for her life. Tests later revealed that she had lesions on her liver and brain. The lesions were later determined to be cancer. Woodlawn’s health improved enough for her to be sent home, where she continued treatment and received in-home healthcare. She was later forced to vacate her West Hollywood, California, apartment due to flooding, and entered an assisted living facility in October. Woodlawn died of brain and liver cancer in Los Angeles on December 6, 2015.