Interview with Barbara Herr

Barbara Herr is a transgender woman, actress, cabaret artist, showgirl and activist whose remarkable life spans more than five decades of LGBTQ+ performance history. Born Robert Hernández in the Bronx, New York, in 1955 to Puerto Rican and Cuban immigrant parents, she grew up between New York and Puerto Rico, an experience that would shape both her identity and her extraordinary artistic career. Barbara moved to Puerto Rico as a teenager and began performing in 1973 under the name Bobby Herr. During the 1970s and 1980s, she became part of the island's vibrant world of drag, cabaret and nightclub entertainment, performing in venues such as Bachelor in Santurce and Stars in Condado. She also worked in theatre and television and toured with a revue connected with the legendary Héctor Del San Juand and Ed Vachan. Later, she toured the Caribbean as a solo artist, headlining her own show during hotel residencies in the Dominican Republic. Two important figures helped shape her artistic life. Antonio Pantojas, one of Puerto Rico's most celebrated entertainers, became her mentor, teacher and close friend, while the legendary Lady Catiria became an important artistic influence. Through them and many other performers of her generation, Barbara became part of a rich Puerto Rican and Nuyorican tradition of transgender and drag performance that has only recently begun to receive the historical recognition it deserves.

 

After building an important career in Puerto Rico, Barbara returned to New York around 1990 because she wanted to live openly as the woman she knew herself to be. Her journey was not easy. Like many transgender women of her generation, she faced discrimination, violence and limited access to safe gender-affirming healthcare. Yet she continued to perform, becoming a familiar presence in New York's LGBTQ+ nightlife and appearing at venues including La Escuelita, The Monster and Friends Tavern. In 2005, Barbara won the title of Miss Continental Elite, recognising a career that had already lasted more than three decades. Her life was later documented in the film Portrait of a Lady: Story of Barbara Herr , produced by Lauren Velez and Julio Colón, and the documentary HERR , produced by Nate and Rob Bailey Millado, while her work also extended to television, film and theatre.

As she grew older, Barbara increasingly turned her own life into art. Her autobiographical shows I'm Still Herr and Trans-Mission allowed her to move beyond the glamour of the cabaret stage and tell deeply personal stories about childhood, identity, transition, relationships, violence and survival. Trans-Mission , which premiered in 2017, earned her an HOLA Award for Outstanding Solo Performance and recognition from the Latin Alternative Theater Awards.

 

Throughout her life, Barbara has remained a powerful advocate for transgender visibility and dignity. Her story connects the Puerto Rican nightclub world of the 1970s and 1980s with contemporary transgender activism and autobiographical theatre. She belongs to a generation of women whose lives were often lived in the shadows, on nightclub stages and in dressing rooms, long before transgender stories became part of mainstream culture. More than fifty years after first stepping onto a stage, Barbara Herr is still performing, still telling stories and still preserving a history that might otherwise be forgotten. Her journey from a Puerto Rican and Cuban child in the Bronx to a legendary cabaret performer, openly transgender woman, actress and activist is not only the story of one remarkable life. It is also a living piece of transgender history.

 

“I didn't know it at the time,
but I was already rehearsing for the life
I would eventually have.”

 

Monika: Barbara, you were born in the Bronx in 1955 to Puerto Rican and Cuban parents and grew up between New York and Puerto Rico. When you look back at that little Puerto Rican child you once were, what do you remember most vividly?

Barbara: I remember being very shy and quiet. I loved playing with dolls at my friends' homes, I loved music, and I loved wrapping a bedsheet around myself like a dress and lip-syncing in front of the living room mirror. I was good at school, but I kept to myself because, even at a tender age, I knew I was different, and there was always some bully who called it out. I was a bullied Puerto Rican kid in the Bronx, and I think that little girl inside me was already there, even though I didn't have the words for her. Looking back, I can see that music and performance were already giving me an escape route. I didn't know it at the time, but I was already rehearsing for the life I would eventually have.

Monika: Do you remember the first moment when you felt that there was something about you that did not fit the role the world expected you to play? Was it a feeling you could understand at the time, or did it take many years before you could finally give it a name?

Barbara: I don't remember an exact moment. For me, it just seemed natural, although I was taught that it was very wrong. Growing up in the 1960s, there was simply no language available to me to explain what I was feeling. Even homosexuality was deeply taboo, and being transgender was practically invisible. So I didn't sit there thinking, "I am transgender." I just knew that the way I felt inside did not match what everybody expected from me. It took me until my thirties to fully understand what that meant.

Monika: In Trans-Mission , you spoke about putting on your mother's wedding dress when you were very young. What do you remember about that moment today, and how do you feel when you think about that child who simply wanted to wear something beautiful?

Barbara: I remember that I knew it would mean trouble if I were caught. That was exactly what happened. My mother gave me a whipping because boys should not wear girls' things or act like girls. I was taught it was wrong, but I also knew how I felt inside. I thought I was the only boy in the world who felt this way. There was nobody on television, nobody in my school and nobody in my neighborhood telling me that there were other people like me. So something as simple as putting on a beautiful dress became this enormous secret. That is one of the reasons I think Trans-Mission was so important to me later, because I finally got to let that child speak. 

“Puerto Rico was my savior.”

Monika: You grew up at a time when there was very little public understanding of transgender people. There were no social media communities, almost no visible role models and very little language to describe what you were experiencing. How did you imagine your future when you were young?

Barbara: Well, there was NO understanding of transgender issues. The word didn't even exist in my world. Those people were banished from society and were often arrested because it was against the law. I never imagined that I would be able to be my true self. I imagined I would identify as a gay man and always be on stage as a drag artist. I also knew I could sing, because I had been singing since childhood and my mother had put me in vocal training. So I thought maybe my future would simply be as a male singer and performer who did drag on the side. I could never have imagined that decades later I would be standing on a stage telling an audience the story of my transition.

Monika: You moved to Puerto Rico as a teenager. What did Puerto Rico represent to you at that stage of your life? Did you feel that you had discovered a new world, or were you still searching for a place where you truly belonged?

Barbara: Puerto Rico was my savior. I had been having trouble at school in NYC because of the bullying. Puerto Rico saved me from that because it was an entirely different way of life. People were courteous and respectful. There were some idiots, but not like in New York. My school experience there was wonderful because I finally had friends at school. They are still my friends today. I knew then that I belonged there. I moved there when I was fifteen, and I stayed for roughly twenty years. It wasn't just somewhere I lived. It became the place where I became an entertainer, where I built my professional identity and where I became part of Puerto Rican culture. I really became a Nuyorican through living between those two worlds.

Monika: Do you remember the first time you met a transgender woman in real life who helped you realize, “That’s me!”?

Barbara: I remember Tiny. She was my cousin, younger than me. She went to New York and returned to Puerto Rico as a woman. Beautiful. She knew that transitioning was in my future, and she tried to help me do it, but I was already a name in Puerto Rico as a drag artist. Transitioning at that time would have meant being banned from every club I worked in. It would have banned me from the theatre as well, and from society. Puerto Rico was very hard on transsexuals. Seeing Tiny was very important because she showed me that this was actually possible. But knowing something was possible and being able to do it were two very different things.

Monika: You began your artistic career in 1973 under the name Bobby Herr. What made you choose to start your career under that name rather than Barbara?

Barbara: It was my name, and I was a man who was an actor and did drag. I was also temporarily back in New York studying hairdressing when I did my first drag performance in the Bronx in 1973. So the beginning was not some carefully designed career plan. I was a performer, I could sing, I could act, and drag became part of what I did. Then I went back to Puerto Rico and really began developing professionally there. Bobby Herr became the name people knew.

Monika: Can you take me back to your earliest performances? What did it feel like to walk onto a stage and present yourself in feminine clothing and makeup before an audience for the first time? Was it terrifying, liberating, exciting, or perhaps all of those things at once?

Barbara: My first time was in NYC, and it was exciting. Although I was not really well prepared, it did not matter because I was talented. My first time in Puerto Rico was spectacular because I was well prepared and had wonderful help with wardrobe, hair and makeup. It was at Bachelor in San Juan in 1975. I never stepped off a stage after that. I started building a career in clubs, theatre and television, and eventually I was performing all over the Caribbean. I worked in places like Stars in Condado and Bachelor, as well as many other nightlife venues, and I even did hotel residencies in the Dominican Republic. Looking back, it is amazing to realize how quickly that first performance became a lifetime. 

“We were not allowed to hang out
in drag.”

Monika: You were part of a remarkable generation of performers who created an entire world of glamour, comedy, music and fantasy in Puerto Rican nightclubs. What was that world really like behind the curtains, after the audience had gone home and the makeup was coming off?

Barbara: It was exactly that! Glamour, elegance and discipline. The makeup came off after the show at the club. We were not allowed to hang out in drag. That always frustrated me. But there was also an incredible work ethic. You had to know your material, your costumes had to be right, your hair had to be right, and you had to know how to hold an audience. I wasn't just working in one little club either. There was a whole circuit, with places like Bachelor, Stars and El, while Zal Zi Puedes and Yerba Buena came later in my career, along with other venues and resort performances. We were entertainers, and we treated it like a profession.

Monika: Antonio Pantojas was not only an important artist in Puerto Rico but also a mentor and close friend in your life. What did he teach you about performing, and what did he teach you about surviving as a person who did not fit comfortably into society's expectations?

Barbara: Well, the lessons I learned from him came from observation. We met in 1975 at Bachelor's, and he became my teacher, mentor and one of my best friends. He always reminded me that I was an actor and that drag was an act. He had no idea that I felt most comfortable as a woman. He threw me on stage to host and do stand-up when I had never done it before. He wanted me to break the ice and become comfortable on the mic. He taught me improvisation through the comedy sketches we did at the clubs. He encouraged me to sing live. He knew that I was different from the bunch he was mentoring. I was special to him.

We also worked together outside the club. I toured with him to island resorts in the Caribbean, and I got to learn what it meant to work as part of a professional travelling production rather than simply appearing at one nightclub. A lot of my instincts as a performer came from watching Antonio. He could command a room without looking like he was trying. That is something you cannot learn from a book.

Monika: Is there one funny, outrageous or deeply touching story about Antonio Pantojas that has never been properly recorded and that you would like future generations to know?

Barbara: There are many, and what many people may not realize is that off stage he was a quiet, humble person. Very smart. On stage, he was a powerhouse, an extrovert and an expert improviser. That contrast was fascinating. You could watch him quietly sitting backstage, and then suddenly he would walk onto the stage and become this completely different force. I learned a lot simply by watching that transformation. He taught me that being a great entertainer is not about constantly demanding attention. It is about knowing exactly when to take it.

Monika: Lady Catiria was another legendary figure in your life, someone you have described as a mother and mentor. What made her so special to you personally, beyond the glamour and the legend surrounding her name?

Barbara: Catiria was not like a mother or mentor. She was helpful in my transition, and we worked together quite a bit. It was a relationship of mutual respect. She was part of a whole New York family of performers around me. There were people like Dorian Corey, Lady Bunny, Perfidia and Sweetie, and we all came from this incredible world of New York and Puerto Rican drag. Catiria was especially important because she understood both the performance world and the transgender experience. She was part of a lineage that I feel very proud to have been connected to.

 

END OF PART 1

PART 2

 

All photos: courtesy of Barbara Herr.

© 2026 - Monika Kowalska

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