Monika: Your chosen name has connections to Casey, your mother Sandra and your drag mother Dena Cass. How did Dena
come into your life, and what did she mean to you at that important stage of discovering yourself and becoming
Cassandra?
Cassandra: Dina came into my life because I used to sneak into the local gay club, and I distinctly remember seeing
Dina for the first time. She came out in an orange palette costume, and she was a wonder. I mean, she was like 300
pounds, but she had star quality.
I just remember thinking, I want to be like that. My relationship with Dina was extremely traumatic. I was very
naive, and I was so in awe of her that I was willing to do anything she wanted. It was very much along the lines of
Mommy Dearest and very much like Ike and Tina Turner. I found Dina extremely abusive. She would always tell me I
would never be pretty. She was definitely not supportive of me wanting to perform. I actually remember when I
decided I was going to perform, we were living together, and I was paying rent every month. I came home, and all my
stuff was on the front porch. She basically told me that she did not want me to transition. She did not want me to
become a burden to her. It was horrible. Dina did some really horrible things to me. I basically say thanks for the
name, but other than that, she basically taught me everything I didn't want to be.
Monika: Do you remember the first time you met a transgender woman in person? What was that experience like, and
how did it make you feel?
Cassandra: Yes, I remember. Remember, this was the nineties in Iowa. This was before the internet. So everything was
through magazines or going to your local gay bar and trying to connect with somebody. I remember I used to take my
mother's hormone pills, you know, because I thought that would help me with transitioning. And I remember going to
the hospital and saying that I wanted to transition and them not understanding what I was talking about.
So basically, they sent me to a support group that was headed by a transgender woman. Now, I thought this was going
to be this incredible, you know, community, but I walked in and it was basically her. And truthfully, she was
everything I didn't want to be. She was not very attractive and living kind of in squalor. So I basically met a lot
of people in the beginning part of my journey who taught me lessons, but more lessons about what I did not want. The
people that I admired were Tula, Caroline Cossey, people I saw on Maury Povich, which is so funny because we are now
Facebook friends and we are about 20 years apart. And I was always drawn to the ones that I thought were, you know,
showgirls who were pretty. I mean, who didn't want to be pretty? I wanted to be pretty.
Monika: You grew up in Iowa and later became such a recognisable San Francisco showgirl. What was the biggest
culture shock when you first entered the nightlife and drag world?
Cassandra: When I first moved to San Francisco, I thought it was a place of plenty. I thought it was completely
accepting. I remember going to the Castro district, and I remember a gay man coming up to me saying, “You don’t
belong here. You should be in the Tenderloin!!!!” I came to find out that’s where many of the trans women were
working on the corners, just trying to survive. What cracked me up is that no more than 15 years later, I was the
celebrity grand marshal for the Pride parade, and I remember giving my speech and saying, “Wow, I wonder where that
guy is now,” lol.
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|
"There were many, many times I was broke
and desperate." |
Monika: Do you remember the moment when you realised, “This isn’t just a character I’m playing on stage. This is
actually me”?
Cassandra: To me, because at the time Hollywood wasn’t gonna allow us to have a career, my performances on stage
were parts of my personality and actually ways that I was acting. I was taking on each and every character.
You know, one of my role models was Madonna. And at the time when I moved to San Francisco, I always thought, well,
what would Madonna do? So I was such a go-getter. I mean, I remember that at some of my performances, people wanted
to take my picture. So I thought, well, why not make a calendar? So I basically got sponsorship, and I produced four
calendars, the Cassandra Cass Fantasy Girl, that I would sell at my performances. I honestly cannot name a
transgender performer in San Francisco at the time who was doing what I was doing. I worked at Divas. I was a
bartender. And then I also worked at AsiaSF, and I was a performer and hostess. And then I also worked at Esta
Noche. I mean, I was working nonstop. I just was super hungry. And then I got the opportunity to work at Harry
Denton’s Starlight Room, and I worked there for 10 years and accomplished so many cool things. I had several
write-ups in magazines and papers that led to many other opportunities.
Monika: When I was talking to a friend who transitioned in the 1990s, she told me, “If you want to transition, you
need three things: money, money and money.” For a young trans woman without family support or financial security,
that can be incredibly difficult, and sometimes a lack of options can push women toward sex work simply to
survive. Many trans women have found themselves in that situation. You managed to avoid that path, even though you
faced rejection and struggled to find work when you first started living as a woman. Was it partly a matter of
conviction for you, knowing that certain choices might help you survive in the short term but could close doors
you desperately wanted to keep open for your future?
Cassandra: Well, I've been at this career, and I've also been blessed to have angels who've come into my life,
who've seen that determination to do the things I want to do, who have helped me. So I've definitely had people help
me, but it's not been because I've sold my body. Oh, yes, oh, trust me, there were many, many times I was broke and
desperate. I just didn't want to sell my body. It came down to that, and I was willing to work. I would be turned
down by 20 different jobs, but all I would need was that one person.
I remember when I first transitioned, I moved to Florida, and I could not get a job. Nobody would give me a job, and
I was in a gay bar, and a guy came up to me and he said, “Hey, you're really pretty.” I said, “Well, that's not
paying the bills. I really need a job.” And he said, “Really? We're hiring a receptionist in the mall at our salon.”
So I remember I got dressed up and I went to the mall and filled out the application. I pretty much thought I had
the job, and I handed it to the manager, and he said, “Oh, thank you. We'll get back to you.” I had been turned down
so many times, I literally grabbed the piece of paper, ripped it up, threw it in the trash, and said, “You're not
gonna call me.” Well, needless to say, on the way out, I was walking through another store, and I knew the friend
who had recommended me for the job there, and he said, “Cassandra, you have to go back.”
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| “I think a lot of girls take the easy way out.” |
Monika: And did you go back?
Cassandra: I said, “I'm not going back.” He said, “Go back.” So I went back, and the manager said, “You're hired.”
It was such a pretty woman moment, and that gave me the opportunity not to have to do sex work.
I think a lot of girls take the easy way out. The reality is it's hard to go to a nine-to-five and clock in, but to
me, I just wasn't willing to do it. I remember when I bartended, you know, I would make minimum wage and a couple
dollars in tips, and I would see these girls, and they were carrying Louis Vuitton bags, and they were like,
“Cassandra, you're so dumb to be working this job. You could be making money.” And I always said, “Hey, a whore on
the corner with a Louis Vuitton bag is still a whore on the corner.” I always wanted respect, and I always thought
that that started with myself.
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?
Cassandra: When I first started, I wouldn't leave the house without a full face of makeup on. But at this point,
I've actually lived as Cassandra longer than I ever lived as my birth sex. I mean, we're 30-plus years in. So to me,
I'm like most women. I dread having to put makeup on or to sometimes even get dressed up. I also think because of my
career with all the modeling and costumes, I've really lived out so many fantasies. I've lived out so many
dream-come-true moments. And I'm at a point now in my life that I just enjoy just being me and realizing that I
don't need all that stuff to be found attractive and whatever.
But don't get me wrong. I still have a full closet full of designer, yada, yada, yada, and a storage unit with my
costumes. And, you know, I can pull it out, but it's more a question of when I want to versus the validation issue.
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or do
you struggle with believing them?
Cassandra: You know, at different phases in my life, compliments were different. I mean, obviously, when I was in my
20s, it was more like, “Oh my God, someone thinks I'm pretty.” I went through that. Then I went through a phase when
I wanted to be taken seriously as an artist. And I didn't find it complimentary that people would just talk about my
body. But now, at 50 years old, yeah, bring on the compliments. I mean, I was just at the store, and a lady came up
to me and she's like, “Oh my God, you're a figure.” So, of course, I love a compliment. And I think now that I'm
older, I appreciate them, and I take them and accept them much more, just because I'm more comfortable with myself.
Monika: You have created a very distinctive, glamorous image for yourself, from your hair and makeup to your
curves, costumes and stage presence. Did you ever feel pressure to meet a certain ideal of femininity, the way I
did trying to look like the women around me?
Cassandra: Did I ever feel pressure? Oh, of course. I think that's part of just being a woman. I mean, you're
constantly bombarded with ideals of beauty. I mean, my father had a stack of Playboys. So I think, as a child, that
was my ideal woman, you know, like the nineties, the curves and whatever. But as I'm getting older, I'm realizing
that beauty comes in different shapes and sizes. But yes, I definitely feel pressure. I mean, every time I go to the
store, I'm still very hard on myself with my figure because, honestly, I built up such a resume with some of the
photos I've done. You know, it's not easy to get older or to change. And I'll be fighting that struggle till the day
I die.
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“I've been very open with my cosmetic
procedures.” |
Monika: How do you choose the gowns and outfits you wear? Do you usually buy them ready-made, have them specially
tailored or altered, or do you sometimes design something yourself? And what makes you look at a dress and think,
“Yes, this is absolutely Cassandra”?
Cassandra: The majority of my costumes I have made myself, or I've worked with a designer. Everything about me is
constructed. It's an extension of my personality or of what I'm feeling at that moment in my life, like if I went
through a breakup or something like that. I mean, everything you see from me comes from my heart. And I'm hands-on
with every single thing I wear.
Monika: You have been remarkably open about cosmetic surgery and the money you have invested in your appearance.
Was there ever a point when you thought, “Okay, enough, I am finally happy,” or does the beauty game always
tempt you to make one more little improvement?
Cassandra: Yes, I've been very open with my cosmetic procedures. Part of that was just to show people that you can
be anything you want to be if you're willing to do the work and, you know, rustle up the money and find the right
surgeons. Yeah, I'm very happy with the way I look. I'm just trying to stay youthful. I was never one of those
people who needed five nose jobs or anything like that. I've always really had a good sense of myself. I just
wanted to have the surgeries to be softer. And once I got to that point, now the surgeries are just about
anti-aging. I'm the type of person who works out every day. I don't believe in having surgery for everything.
Monika: You know, many of us feel the pressure to “pass” as women, and even after surgeries, society keeps
judging us. You look like a million dollars, so I’m curious, how do you personally deal with the outside world’s
expectations of femininity and beauty? Do you feel that, at some point, you stopped trying to meet other
people’s standards and simply decided to become the woman you wanted to be?
Cassandra: I think the thing about me is that once I knew what I wanted to look like, I did it for me. Let me just
make this clear. Everything I've ever done is because this is the way I wanted to look. This was my ideal of a
beautiful, perfect woman in my eyes. As far as society, I've never followed society's rules anyway. I mean, when
you think about how I've lived, it's just something I gravitate toward. I love being a blonde. I love being curvy.
I love being vivacious. That's just something that is my own standard. I'm not trying to fit in with society.
Society can kiss my butt. I mean, you're never going to be happy trying to fit other people's ideals of what you
should be. This is my journey in life, and I'm truly doing what makes me happy.
Monika: You appeared on CSI, Trantasia, Wild Things, What’s the T?, Strut and Hooked on the Look. How different
did it feel to be yourself on television compared with performing on stage?
Cassandra: Well, when you're acting or you're in a reality show, it's different than on stage. Nothing compares to
the energy you get on stage from a live audience. I mean, it just makes you come alive. I enjoy all facets of
entertaining, but stage is just so tangible. But I will say, as far as a legacy, the TV shows and stuff will stand
longer than my stage performances.;
END OF PART 2
All photos: courtesy of Cassandra Cass.
© 2026 - Monika Kowalska
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