A Look Back at Holly Woodlawn, Andy Warhol’s Trans-Latina Protégée and Transgender Movement Heroine

Holly Woodlawn Andy Warhol BELatina Latinx
Photo Credit Jack Mitchell/Getty Images

“‘Walk on the Wild Side’ made me immortal, honey,” Holly Woodlawn said in an interview back in 2013, “for what that’s worth.”

The transgender actress and pioneer of trans activism spoke to The New York Times two years before she passed away in the winter of 2015, recalling singer Lou Reed, who wrote her into history through his iconic song, the anthem of a generation as prolific as it was fleeting.

As that first verse recounts, Holly hitchhiked from Miami to New York at age 16, plucked her eyebrows, shaved her legs, “and then he was a she.”

Although, actually, Holly Woodlawn always knew she was a woman.

The Price of Freedom

Woodlawn was born in Juana Díaz, Puerto Rico, in 1946, the daughter of an American soldier of German descent and Aminta Rodríguez. After her father abandoned her mother, the family moved to Miami Beach following her stepfather, Joseph Ajzenberg, who found a job at the Fontainebleau Hotel.

Despite taking her father’s name, and having transformed her own from Haroldo to Harold, she came out of the closet at age 16, and adopted the name “Holly.”

“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,” she recalled in her memoir, A Low Life in High Heels.

Although she repeated many times that she had adopted her new name in honor of Holly Golightly, the protagonist of Truman Capote’s Breakfast at Tiffany‘s, in her memoir she also recounts other versions, surely clouded by time.

In some she mentions that the Woodlawn came from the name of the famous cemetery, in others she assures that it was an episode of I Love Lucy in which a subway train sign appears that reads Flatbush Avenue and Woodlawn.

The fact is, once luck was on her side, the name would stick.

Taking a Walk to the Wild Side

The young woman hitchhiked to New York, and ended up in a prostitute circle “of any and every gender,” trying to survive, and learning to put on 25-cent lipsticks from subway vending machines.

“Atlanta, Georgia, of all places — you could expect to be tarred and feathered and murdered in those days! But we survived and I remember the first time I saw New York: the Emerald City. I thought the sidewalks were made of diamonds because of the specks of mica in the asphalt,” she told The Guardian in an interview in 2007. “It was 1962. Marilyn had just died. I lived on the streets like everyone does when they run away. I met some girlfriends who took me in and we found a place in Queens. I was really lucky. I met this guy who fell in love with me and asked me to be his girlfriend. I started taking hormones for a sex-change and lived as his wife, working in the days as a clothing model at Saks Fifth Avenue. Oh, the things I did! And for six or seven years they never knew I was a boy. Not a clue!”

Archivist, model, go-go girl and even Miss Donut, Woodlawn would embrace her new identity with the freedom offered by early 1962 New York during the day, and the toughness of trying to survive one night at a time.

While Holly was trying to survive on the streets, a young illustrator-turned -controversial artist had his first solo exhibition at Eleanor Ward’s Stable Gallery, featuring images of soup cans.

Then There was Andy

During one of the many events at Andy Warhol’s studio, the Factory — at its second location, on the sixth floor of the Decker Building — in 1968, Holly met luck, enchanting the eye of the artist and collector of eccentricities, who would introduce her to his friend Jackie Curtis.

Curtis hired the young Puerto Rican woman as a chorus girl for the revival of her play Glamour, Glory and Gold: The Life and Legend of Nola Noonan, Goddess and Star, where she would share the stage with a young Robert De Niro, who played the 10 male roles.

“I had a scene with him in which he played a Jewish producer; I was auditioning and he felt me up,” Woodlawn wrote in her memoir.

A year later, and after her appearance in Curtis’ second play, Heaven Grand in Amber Orbit, Woodlawn already considered herself another of Warhol’s stars, but one who had no “aristocratic” roots.

“Hers was a different kind of aristocracy, one formed not from bloodlines but brazen moxie, heedlessness in the face of convention and determination to claim for herself the glamorous existence denied her by some obvious misalignment of fate,” Guy Trebay wrote in his 2015 obituary for The New York Times, distinguishing Holly’s career from other Warhol protégés such as Brigid Berlin, Baby Jane Holzer or Edie Sedgwick.

Although she was still an ordinary mortal for Andy, her egomania caught the attention of Paul Morrissey, Warhol’s co-producer who would eventually cast her as Joe Dallesandro’s co-star in his legendary film Trash, where for the first time a transgender woman would play a heterosexual cis woman.

BELatina Holly Woodlawn Latinx
Woodlawn’s story was immortalized in the first lines of the Lou Reed song ‘Walk on the Wild Side.’ Here she is pictured in 1971 when she was 25

“They wanted me for one or two scenes at first,” she said in her 1970 Village Voice interview. “Paul Morrissey said, ‘Do this, do that, fabulous,’ and so they kept adding to my part. I worked six days at $25 a day. Except for the last scene, everything was done in one take. The clothes, the dialogue, like, everything was mine because the character I play is me. I’ve been in those situations.”

In fact, Morrissey rewrote the entire role for Holly, who, in turn, preferred to improvise, giving the murky film a little light in her funny come-backs, which guaranteed her a role in the director’s next film, Women in Revolt, a satirical look at the women’s rights movement.

“You live in a hovel, walk up five flights, scraping the rent. And then at night you go to Max’s Kansas City where Mick Jagger and Fellini and everyone’s there in the back room. And when you walked in that room, you were a STAR!” she remembered.

In Women in Revolt, Woodlawn would mark another “first” in the history of cinema, being one of the first people to say the word cunt on the big screen.

And… Scene

After her brief moment of fame, Woodlawn made some appearances, such as in the documentary Is There Sex After Death?, and in the low-budget 16mm musical Scarecrow in a Garden of Cucumbers. 

Her last attempt and, for some, her most ambitious performance, was in Broken Goddess, a 1973 black and white short film originally written for Bette Midler, in which Holly appears with heavy Kabuki makeup.

She also tried out for cabaret in the late 1970s in Manhattan, but life would take her back to the beginning, ending up back in Miami, waiting tables at a restaurant in Benihana and working for her father’s tax business, according to The New York Times.

“I felt like Elizabeth Taylor,” she said remembering the best moments of her life. “Little did I realize that not only would there be no money, but that your star would flicker for two seconds and that was it. But it was worth it, the drugs, the parties; it was fabulous.”