Interview with Deena Kaye Rose

Deena Kaye Rose is a remarkable figure in American music and literature, known for her creativity, resilience, and honesty. As one of Nashville’s most recognized songwriters of her time, she has over 400 songs published, with around 200 recorded and released worldwide. Her collaborations with legendary artists, including Johnny Cash, secured her place in the history of country music, with songs such as Any Old Wind That Blows becoming timeless hits. She also penned songs that reached audiences across the globe, shaping the sound of an era in country and popular music. What makes Deena’s story even more compelling is the way she has intertwined her artistic journey with her personal one. After years of success in the music industry, she embraced her true self and transitioned later in life, choosing authenticity over fear. She has spoken openly about the challenges and joys of that decision, offering wisdom to others who may be standing at similar crossroads.

 

In her autobiographical book Some Days Are Diamonds (2016), she reflects not only on her career and creative process but also on the power of living one’s truth. Her life has taken her through Los Angeles, New York, and Nashville, always in pursuit of music and creativity. Along the way, she has performed, collaborated with some of the most iconic names in the industry, and built lasting relationships with fellow artists. Yet her work extends beyond music. As a writer and lecturer, she has given voice to transgender experiences in ways that resonate deeply with both trans and cisgender audiences. Today, Deena continues to embody a fearless artistic spirit. She writes new music from a transgender point of view, reimagines her past creations through the lens of her present self, and inspires countless others with her humor, humility, and insight. Her story is one of courage, reinvention, and devotion to the creative life, reminding us that art and authenticity are inseparable companions.

 

Monika: Today it is my pleasure and honor to interview Deena Kaye Rose, an American writer, lecturer, one of the most recognized Nashville songwriters of her time with over 400 songs published and around 200 of those recorded and released worldwide, the author of the biographical book titled “Some Days Are Diamonds” (2016). Hello Deena!

Deena: Hi, Monika! It is an honor to be invited to share a bit of my humble story with you. Thanks, bunches.

Monika: You are a woman of many talents. Could you share a few reflections on your remarkable career?

Deena: Well, I appreciate your very kind words. I have often thought that even a stray dog finds a ham-bone now and then! So I have stumbled upon some minor successes in the world of entertainment.

Being creative is absolutely the most important part of my life; whether that is writing songs, performing on stage, or recreating myself as a woman. Having lived in Los Angeles, New York City, and Nashville, the world of show business is filled with so many inspirational people. My intent was to TRY and write songs, rather than not make the attempt and spend the rest of my days wondering if I might have done it - but I didn’t give it a chance.

Nashville Publicity Photo.

Monika: Most people remember the songs you wrote for Johnny Cash. What are your memories of working with him?

Deena: Johnny Cash heard a tape of about seven of my compositions and he called me. He said, “Hello, this is Johnny Cash,” and at first I thought it was one of my friends trying to prank me. He asked me to come out and talk to him. Well, I was about five miles away and I think I made it in about four minutes! He praised my tunes and said they were “not just a bunch of words.” John signed me to his publishing company and gave me a draw of $100 a week.

Monika: What was it like to share that kind of personal and professional connection with him?

Deena: We had some terrific talks, one on one. He recorded and released four of my songs, including his number one recording of my song, “Any Old Wind That Blows.” The best advice he ever gave me was, “Sing louder!”
Monika: In what ways did your experience as a session musician shape your understanding of the needs and expectations of artists looking for your songs? 

Deena: Very much so. And it gave me a close relationship with other professional Nashville musicians. These girls and guys gave me a lot of tips concerning recording artists who might be looking for a particular type of material.
Monika: Do you have a favorite among the many songs you have written? 

Deena: My songs are like my children. While each tune may have unique qualities and a special history that I like, I could not choose one over another any more than I could choose one child over another. I always feel that I have two favorite songs: the last one and the next one! The excitement an artist has for a new creation is very exhilarating. And when that excitement wears off, the creative muse nudges me with another idea.

Monika: Where do you usually find the inspiration for your songs?

Deena: My inspiration has often come from the art of others. Mary Cassatt’s painting “Portrait of a Young Woman in Green” might touch me and leave me with such a glow that I want to create too, not to copy her genius but to make something with my own talents. Out of that feeling might come a new song. And I love to speak with persons who give me a line or tell me a story that becomes a nice musical work, to express what they might feel but cannot say.

Late 1970s in NYC.

Monika: How has your transition influenced the way you perceive the world artistically, and what does being a transgender artist mean to you?

Deena: Now, I am artistically fearless! A lot of my time when I was trying to be a guy was consumed with the paranoid acts of what I felt was self-protection.
Monika: In recent years, contemporary music has seen a growing presence of transgender female artists, such as Mina Caputo of Life of Agony, Laura Jane Grace of Against Me!, Marissa Martinez of Cretin, Amber Taylor of The Sexual Side Effects, Namoli Brennet, Sissy Début, and Jennifer Leitham, and many others. How do you feel about this new wave of transgender performers? 

Deena: I celebrate them all! Wonderful artistic courage, every one of them. When I met Jennifer Leitham, I told her she had inspired me in a very deep way in how, after transition, she had publicly embraced her achievements before transition, her musical career as a guy. She said, “Well, I really didn’t have a choice!”

Monika: What do you think is the most common misconception about transgender people in the arts?

Deena: Too often the impression I have gotten through the years is that transgender folks have all been incapacitated by gender dysphoria, that we were hiding in a shuttered room somewhere just waiting to transition so that our lives could begin. But that is certainly not true. I am thrilled to see so many post-transition people coming out to claim their successes in their previous personas.

Monika: Can you share a few examples of transgender people whose accomplishments have impressed you?

Deena: Just to mention a few as examples, Martine Rothblatt, the founder of Sirius Satellite Radio, Laura Jane Grace, already a star as the male lead singer in the band Against Me, who slipped seamlessly into the same spot as her female self, the recent story that the Wachowskis, the genius movie makers, are both transgender, and, of course, Caitlyn Jenner. Now everyone can say I knew someone before she transitioned!

Monika: Do you believe that the presence of transgender artists in music will continue to grow?

Deena: Yes, I do hope we see more and more transgender musical artists and I would hope that someday the TG part of a performer’s story will be a very minor deal when really great music should be the main thing. I once heard the legendary guitarist, Chet Atkins, say, “There are only two kinds of music: good and bad!” And I am eager to tie my humble musical accomplishment to the true fact that I am transgender, that even a country music guy from Nashville who wrote “East Bound and Down” from the Burt Reynolds film Smokey and the Bandit is not immune to the state of being trans. It chooses us, not the other way around.

Performing on a Nashville Network TV Show.

Monika: How would you describe the current situation of transgender women in American society?

Deena: We are more visible. Our bravery often comes from others who have taken to the internet to wrap collective arms around one another, to provide support to our trans sisters and brothers.

Monika: How has growing up in a time of greater social stigma shaped your perspective on this increased visibility?

Deena: Being a “mature” lady myself, I grew up in a time when being a person who wanted to be the opposite gender was about the worst social stigma that one could possess. With the advent of the internet, we find, hey, I am not the only one. There is a great Barry Manilow song, which I wish I had written but didn’t, called “All the Time.” It is certainly a great tune about feeling alone when others like me were there all the time. I recommend a listen. This tune is about the US.
Monika: What inspired you to write your autobiography?

Deena: For that same reason of community solidarity that I spoke of before. When I met Kristin Beck, she told me there was no reason for me to allude to my old dead name; that I could move to Seattle, transition, change all of my gender markers, and no one would ever need to know. I said, “Yes, Kristin, but I would know. And it would be unfair to my TransSisters if I were to choose living in stealth myself while others like Kristin Beck are putting themselves and their lives on the line in order to achieve gender equality for all.”

Monika: How did you hope your story would help others facing similar challenges?

Deena: My story is my attempt to say to others like myself who have struggled with the idea of transition and what there might be to lose, that all of the negative circumstances that I had imagined never came to pass! Worrying about those “maybes” was an exercise in wasted energy and wasted tears.

Monika: How did it feel for you personally after your transition?

Deena: The worst day I have had since my transition to a full-time lady is better than the best day I had in the dozen or so years before that. I was prepared for disappointment; I was not really prepared to be so very happy! Each morning, I look in the mirror and think, I am a woman! Most times, I start to tear up just from the very emotional memory of feeling that I would never see this reflection of myself. “Hello, Lady. Where have you been?” She was there all the time. A transfriend once said to me, “You know, you have to learn to act like a woman.” I said, “No, I have always been a woman. I am just learning to act like a lady!”

Her book via Amazon.

Monika: What lessons from your experience do you think could help other transwomen, especially those considering a later-in-life transition?

Deena: Well, as I have said, I am a “mature” lady, and being such, I would tell anyone who has late-in-life doubts about transition that it is only the wrong time when there is no more time. I am delighted to be an older woman, for if I am left with twenty more years, twenty more months, or twenty more minutes, this is the right thing to do with the rest of my life. And I am delighted to know my true soul has finally come out to meet the world.
Monika: At what age did you begin your transition, and what was that process like for you?

Deena: As I said, I am a late-in-life lady! I began HRT about six years ago, and around that time I started to rid myself of material ties to everything. I sold a property, held yard sales, gave away “stuff,” sold musical instruments on Craigslist, and made numerous donations to charities.

Monika: How did you prepare for the transition in practical terms, especially regarding your belongings and finances?

Deena: I had come to Nashville with everything I owned in my old blue Chevy and $800 in cash in a Hershey’s chocolate tin. My plan was to leave Tennessee in much the same way, only in a different gender. I put everything in digital form, online, or in mail forwarding plans, and I took all of my leftover boy clothes to Goodwill. All of my music accounts were online, my credit cards were paperless, and all of my banking was online except for one small local account for petty cash, which I closed out for travel money. It was a little over $1,000.

END OF PART 1

PART 2

 

All the photos: courtesy of Deena Kaye Rose.

© 2016 - Monika Kowalska

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