Monika: Your life has been connected with many extraordinary performers, including women and entertainers who are
no longer here to tell their own stories. Which forgotten transgender performers would you wish people today knew
about, and what do you feel history has failed to understand about your generation?
Barbara: Honestly, there are too many to list. My Boomer generation was by far the most glamorous generation of
entertainers because we were the first to break the barriers. We were working when there was no internet, no social
media, no transgender entertainment industry and very little protection. We had to create our own stages and
sometimes even create our own jobs. A lot of those women were extraordinary actresses, singers, dancers and
comedians, but history tends to remember only the most famous names. There were hundreds of women who kept the clubs
alive and made a living entertaining people while society pretended we didn't exist.
Monika: You performed as a drag artist long before you were able to live openly as a transgender woman. Looking
back, do you see your years as a performer as part of your journey toward understanding yourself, or were your
artistic identity and your personal gender identity separate experiences at the time?
Barbara: Absolutely! From the time I was a child, I could sing. I had a good voice. My mother had me in vocal
training, and I presumed I would be a male singer. Drag sort of fell in my lap as a fun thing to do. It actually
showed me that my stage persona was where I felt most comfortable. The interesting thing is that I could separate
"Bobby the actor" from myself for a while, but the more I performed, the harder that separation became. The stage
gave me permission to be something that I wasn't yet ready to admit I wanted to be in everyday life. So yes, the art
was absolutely part of my journey.
Monika: After building an important career in Puerto Rico, you eventually returned to New York because you felt
you needed to live your life more openly as a woman. Was leaving Puerto Rico one of the hardest decisions you ever
made?
Barbara: Leaving PR devastated me. Adjusting to NYC again after 25 years was very difficult and challenging. I had
spent so much of my adult life there that Puerto Rico was home to me. But I had reached a point where I needed to
live my truth. I knew that I could not fully transition there and continue the career I had built because the
discrimination against transgender people was too strong. So I came back to New York in 1989. I had to start
rebuilding a life in the city where I had originally grown up, but I was now a completely different person.
|
|
"We had to create our own stages and
sometimes even create our own jobs." |
Monika: So many transgender women have had to choose between safety, family, work and authenticity. What did you
have to give up, or risk, in order to become Barbara Herr openly and fully?
Barbara: I really gave up nothing. I always had family support, I always worked, and I never really felt unsafe.
That doesn't mean the transition was easy. It means that I had certain things in my life that many other women did
not have. I was able to keep working, and when I came back to New York, I continued performing at places like
Sally's and La Escuelita. I eventually became part of the nightlife again, even though I was now living openly as a
woman. I was fortunate in some ways, and I don't want to pretend otherwise.
Monika: Was there a particular moment when you stopped thinking of womanhood as something you performed on stage
and began to feel that you were simply living your everyday life as the woman you had always been?
Barbara: Yes. 1986. That is when I planned my move. I had already started thinking seriously about what my life
needed to become. There was a point where I knew I couldn't keep dividing myself into the performer and the person
forever. The stage had shown me where I was happiest, and eventually I had to take that feeling off the stage with
me.
Monika: When you came out, did your mother embrace you as her daughter? And do you feel any connection to her in
the way you look, carry yourself, or even in your style and mannerisms?
Barbara: Unfortunately, my mom passed away in 1973 when I was 17. She was 42. I was not out, although we never
discussed it. She knew. I see her in me now at times. Other times, I see my dad. Losing her so young meant that I
never had the opportunity to have that conversation with her as the woman I eventually became. That is something you
cannot go back and change. You just carry it with you.
Monika: I remember the time right after my transition, it was pure euphoria. My closet is still full of dresses
and shoes that I literally bought by the dozens back then, and I must have tried on hundreds. I felt like I had to
make up for all those years that were taken from me. Did you feel the same way?
Barbara: No!! I was petrified and self-conscious. I was 35 when I transitioned. It's easier when you are younger. I
wasn't running around thinking, "Finally, I can buy everything!" I was worried about everything. I had spent so many
years being a performer that suddenly having to simply walk down the street as a woman was a completely different
kind of performance. Eventually, everything fell into place, and I am no longer self-conscious. But those early
years were very different from the glamorous picture people might imagine.
|
| "The art was absolutely part of my journey." |
Monika: Your generation often had to navigate dangerous and sometimes unregulated paths to obtain hormones and
gender-affirming care. How different do you think the experience of transition is for transgender women today, and
what do you wish younger women understood about the risks and courage required by the women who came before them?
Barbara: In my time, everything was on the black market. Hormones, silicone, all of it. There was no "transgender
healthcare" like we have today. Everything was risky. My advice to the new generation is to stay away from silicone
and anything that is not legal. Do everything medically. We have that option now. I honestly thought I was too old
to have gender-affirming surgery when I eventually had it. I was 62. I had wanted it for years but couldn't afford
it. Obamacare made it possible for me, and I am very happy that I finally did it. But surgery is not a requirement
for being transgender. Everyone has a different path.
Monika: You have spoken honestly about relationships and about the violence and disappointments you sometimes
experienced with men. After everything you have lived through, what does love mean to you today?
Barbara: I only experienced violence once. The rest have been disappointments because of betrayal, opportunists or
being used as a fetish. Yet through it all, I still believe in love. Sometimes it is not meant for some of us, but
it does exist. I have had relationships that taught me beautiful things and relationships that taught me very
painful things. I don't regret loving people. I just became better at recognizing who deserved my love.
Monika: You have survived experiences of violence simply for being yourself. Without asking you to revisit
anything you would rather leave in the past, how did those experiences change your relationship with the world?
Did they make you more cautious, or did surviving them make you even more determined to live openly?
Barbara: I have always been a warrior and a survivor. I have been cautious my entire life and continue to be,
especially with the current political and social climate we are in. One of the worst incidents happened after I
returned to New York, when I was living in Corona. I was attacked by a group of men, and fortunately, the
perpetrators were prosecuted and received twenty-year sentences for a hate crime. That experience stayed with me. I
later moved to Sunnyside. I don't live my life terrified, but I don't walk through the world believing that
everybody has good intentions either. Survival teaches you to pay attention.
|
| "I have always been a warrior and a survivor." |
Monika: One of the things that makes you different from many classic female impersonators is your extraordinary
ability to talk to an audience. You tell stories, make jokes and create a relationship with the people in front of
you. When did you discover that your own voice could be as powerful as any song you performed?
Barbara: It came with time and experience. Antonio helped with that because he pushed me onto the microphone and
made me host and do stand-up before I thought I was ready. Eventually, I discovered that I loved talking to an
audience as much as performing for them. I became very conversational on stage. I can tell a story, make a joke, do
a lip-sync number and then switch back into conversation. I have performed in both English and Spanish, and that
connection with an audience became one of the things I valued most about cabaret.
Monika: Complete this sentence: “A real showgirl is not defined by her body, her costume or her makeup. A real
showgirl is…”
Barbara: A disciplined professional. You can have the most beautiful costume in the world, but if you don't know
your material, don't respect your audience and don't understand that performing is a job, you're not a showgirl.
Glamour is wonderful, but discipline is what keeps you working for fifty years.
Monika: In 2005, after decades in the entertainment world, you won Miss Continental Elite. What did that victory
mean to you personally? Did it feel like recognition, vindication, celebration, or perhaps something even more
complicated?
Barbara: It meant ALL of the above. That victory was bittersweet for me because I should have won the regular
Continental a couple of times before Elite. Elite was not something I wanted until I won the regular. When I won
Elite, I just let it all go after seven years of competing. I crowned the new winner one year later, and I never
returned. Winning was wonderful, but the biggest feeling was finally being able to close that chapter. I had spent
years competing, preparing, travelling and putting everything into those pageants. After that, I knew I had other
things to say and other stages to conquer.
Monika: Many of us feel the pressure to “pass” as women, and even after surgeries, society keeps judging us. How
do you personally deal with the outside world’s expectations?
Barbara: Honestly, those days of worrying about passing or not are gone. I don't even think about it. I just go
about my day. I have spent too many years worrying about what other people think to waste the rest of my life doing
it. I'm an actor and entertainer, and yes, I like looking glamorous. But there is a difference between looking the
way you want because you enjoy it and desperately trying to convince strangers that you are something. I know who I
am.
|
| "Education was simply another part of my life." |
Monika: You earned a degree in Social Sciences from the University of Puerto Rico while building a life as a
performer. People often reduce transgender showgirls to stereotypes and forget the intelligence, education and
ambition behind the glamour. Has being underestimated ever become one of the things that motivated you?
Barbara: I have never felt underestimated. Education was simply another part of my life. I loved theatre, acting and
performing, but I was also interested in learning and having an education. People sometimes imagine that because
someone works in nightlife, that's all she knows. That was never me. I could be backstage worrying about a costume
and then be thinking about something completely different. I've always had different sides to me. I was also a
cosmetologist for many years.
Monika: You eventually began turning your own life into theatre through shows such as
I'm Still Herr
and
Trans-Mission. What was more frightening: standing in front of an audience in full showgirl glamour, or standing before them
emotionally exposed and telling the truth about your own life?
Barbara: Definitely being emotionally exposed as an actor telling my own story. I have performed glamorous cabaret
for decades. I know how to put on the hair, the makeup, the costume and become an entertainer. That is easy compared
with standing on a stage and saying, "This happened to me."
I'm Still Herr
was more cabaret-oriented and allowed me to use the performer I had always been, but
Trans-Mission
went much deeper. I wrote it and performed it, with Luis Caballero directing, and suddenly I couldn't hide behind
another character.
END OF PART 2
All photos: courtesy of Barbara Herr.
© 2026 - Monika Kowalska
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