Trans Country Crooner Jaimie Wilson Strumming His Way to Success

NEW YORK, NY – For twenty-one year old Jaimie Wilson, nothing beats the feeling of rambling along in his custom Jeep Wrangler 4X4, headed for a gig to perform his beloved country music in his adopted home state of Florida. Shirtless, tanned, fit, and blonde haired, he looks like most every other young man his age who is entering adulthood trying to figure out where his path will take him.



As the Jeep rolls down the freeway, his guitar and overnight bag perched in the back seat, windows rolled down, he sings along to the radio or a CD, the oversize off-road tires humming as the miles fly by for accompaniment.



But, it wasn’t always like this, and for Jaimie, life was actually pretty difficult. He grew up the youngest of four children in rural Livingston County, Michigan, near its county seat of Howell. An area of Michigan that is deeply red, religious, and conservative. He and his three older brothers lived on their family’s horse farm, and Jaimie had a secret which he knew he couldn’t share with his closest friends or his own family. He knew, from as early as age five, that he wanted to be a boy, in fact, Jaimie knew he was going to be a boy. However, a decade went by before he began to realise his dream, for you see, Jaimie, was designated a girl at birth.



He described growing up as difficult, hardly permitted to be even a true tomboy by his deeply religious and conservative family, who were opposed to anything related to the LGBTQI community, to the point there was never, ever, any mentioning of LGBTQI people.



In fact, Jaimie waited until the second semester of his senior year of high school to come out. Knowing that his family was hardly affirming, and like most LGBTQI youth, he had kept a very low profile. February 4, 2015 though, became Jaimie’s red letter day as he relates:



“When I realized that I was "different" I decided I would never come out. It just wasn't an option for me because I knew how my family would react. It was something I was just going to have to bury deep and deal with. But I woke up one morning and decided I was done living a lie.



A few days earlier I had watched a viral video by Ruby Rose titled "Break Free" and it was like a light bulb went off. I needed to break free. So I called a nearby salon and made the earliest appointment I could. I cut my long flowing locks. I didn't tell anyone I was doing it. I just came home that day with short hair and dressed in men's clothing.”



Jaimie had spent countless hours searching YouTube and other internet portals, trying to find youths like him, trying to find himself and his place in a world where he could fit in. He describes grabbing hand-me-downs from his older brothers without their knowledge to wear as his way of being able to be a boy, at least partially, but always when he was alone. He related that he’d tuck his long flowing hair up under a baseball cap, throw on a pair of jeans and a shirt and transform himself, at least for the moment, into his ‘real self’.



That winter day when he decided that he needed to live as his true and authentic self was traumatic.



“My mom and dad did not react well. There was a lot of crying and confusion. A lot of ridicule. They made it impossible for me to stay with them. Still in high school I was forced to move out and fend for myself.



One of my brothers initially was supportive but his opinion changed shortly after I came out. My family (mom, dad, and brothers) have progressively just gotten worse about my transition and we no longer have a relationship.”



Jaimie’s anchor, in what had become a tumultuous and oft times drama filled life, was his love of music. He had started playing piano at around the age of five and picked up playing guitar when he was sixteen. His mother had an old guitar she was getting ready to throw out and she offered it to him first. Music, he says, became his escape.



One of the primary outlets for his musical creativity became YouTube. In a video posted on October 15, 2013 prior to his transition, Jaimie wanted to raise awareness regarding suicide among LGBTQI youth with an original song he’d written. He noted:



“My hopes for this song is not to make you sad...but to inspire you to reach out to others, because a friend, can sometimes be a life saver. Every single person is important, and if anyone ever needs a friend or someone to talk to I'm here.”



Music, he explains, is much more than just a personal passion, it is a way to contribute - to give back.



“Being transgender, I have always struggled with trying to make others happy but I want to show that it's okay to break free. I'm hoping with these words I can bring the community together and encourage others in similar situations to be true to themselves.”



It was the realisation that his family was going to remain unsupportive and unyielding in their opposition to his decision to live his life authentically that crystallised his decision to move away from the confines of his Michigan hometown.



“I like sun and water and warm places so moving to Southern Florida made sense,” he says.



That and he really wanted to move at least somewhere that would be a place he felt where he could transition comfortably and where he had friends who were supportive.



Jaimie, however, knew that he was going to be proactive and open about himself. By this time and not shy at all, he documented his journey in countless pictorial posts on social media as he made his transition. Candid photographs and then several contests he sponsored for ‘binder’ giveaways to help fellow female to male trans people like himself.



He picked an Instagram handle that was his bench mark, the date of his medical transition. His selected screen name? Tboy61915.



“I started my medical transition [on] June 19, 2015 and top surgery in September 2015. It was important to me to get top surgery because I didn't identify with having a female chest,” he says, adding “It was an amazing day and a weight off my shoulders!”



“I started my Instagram account June of 2015, a few days before starting hormone therapy. I started the page to document my transition and changes. In the early stages of realizing I was transgender, I would look at FTM guys on Instagram and look at their progress and top surgery and voice changes. It was extremely helpful and inspiring. I wanted to make sure I had a place to document my journey as well so I started an Instagram for that.”



All the time, music is his outlet and his motivation which drives him to attain success. Yet, he also knows that as his story gained greater awareness on social media he wants to help out and not sit back and be silent.



“My motive for being a trans activist is spreading awareness. I am in a position to be able to help others and be visible so I do what I can. I had no support from family or friends so I know how helpful it can be to have someone give out binders, donate to their GoFundMe campaigns, speak for them when they don't have the voice. It's very important to me,” he says.



As he continues to rack up thousands of views on his YouTube videos and has built up to nearly 200,000 followers on Instagram, he pursues his musical career, interweaving his music with an unabashed commitment to his trans advocacy. On the subject of music and genre he notes:



“I grew up listening to country music so that's really my roots and what I enjoy to write and sing. I love all genres of music and get a lot of requests for pop covers as well.



Recently I've gotten more into the production of music. I used to have my songs recorded at a studio but now I've been doing all of the production, recording, mixing, mastering myself. I'm looking forward to working with more people in helping them take their ideas and make them a reality.”



One recent song, "Soldier," posted to his YouTube channel last month talks about his take on personal battles people face daily, but also his conflicts as a trans man.



“I wrote the song to speak to everyone, because whether they show it or not every single person is going through struggles in their life. We are all soldiers fighting our own battles. In the song I express that although life is difficult, love can help you through anything.



For me personally, the song "Soldier" was about living my own truth while battling against hurtful words and actions. Even though coming out was very hard for me and I endured a lot of pain, I did my best and do my best to keep love by my side. Again, love can help you overcome anything.”



He also DJ’s around Florida as well as performs at gay bars, pride events, and charity events.



When asked why he wasn't living in either Nashville, home to Country Western, or even Memphis, he was direct and blunt:



“Nashville and Memphis are not trans inclusive as far as the country scene goes. I think that country music does not have very much LGBTQ+ representation. I would really like to break that barrier."



But that is something Jaime is convinced he can help change. Not long ago he says, a talent agency contacted him after watching his videos, they were excited about his work, but after they were informed he was trans - suddenly they wanted him to perform in another genre other than Country-Western. Not something he’s interested in.



"The support I have received from the LGBTQ+ Community and allies has shown me that anything is possible! I don't need to have the country music scenes approval...I'm coming whether they like it or not!



I'm very thankful for all the support I have received and continue to receive. My supporters make this all possible for me, I don't even think they know how much they mean to me.”



Is there room for a transgender country music star? Jamie is convinced there is.



“Absolutely. I think doing so would really help make trans visible. I am a country singer who happens to be trans. For me it is very important to be open about being transgender, I take it as a opportunity to spread awareness. And yes, although some country stars may be accepting of the LGBTQ+ community, there is not much representation of LGBTQ+ artists in country music like there is in mainstream pop.



I think it would be amazing to change that. I'm not sure exactly what to expect being a trans man trying to break into the country music scene. But I grew up on country music, it has a special place in my heart, and I'll keep singing it until I can't sing anymore.”



He sees fellow musician Steve Grand, a singer, songwriter who’s been acclaimed by some to be the first openly gay male country performer who was able to attract mainstream attention after building a massive following on social media and the internet, as an example that he can follow. But he’s dedicated to continuing his work building his own following and his own fan base. He continues to also remain dedicated to his advocacy work as a vital component of who he is as a person, and as a performer.



Jaimie’s response to the question of whether or not he writes for a specific audience and what he found for inspiration as a songwriter was quite poignant:



“I don't have anything specific that inspires my writing. Some days I sit down and write an entire song and it seems to just come to me. Other times I find myself emotionally returning to a past experience to get the inspiration to write about what happened to me in hopes someone else out there can relate. Some songs are just happy songs, others are intentionally written to take me, or people listening, to a place where they feel vulnerable.



Music is something I do to make myself feel complete; I would still be writing and singing even if no one wanted to hear. I don't write with a specific audience in mind. I never want to limit myself or listening audience. I just sing and write what comes naturally to me, and I'm very grateful for anyone who enjoys!”



Asked if he may consider auditioning for one of the popular talent shows such as The Voice, X-Factor, or even America’s Got Talent he was coy but didn’t rule those possibilities out as he noted:



“I do gigs around Florida, but I'm not limited to Florida. I have a 10 state tour and 2 international stops coming up this year.”



For now, at least, he’ll continue to pursue his dream, working hard on building his fan base, writing and performing his songs, dee-jaying gigs, and strumming his guitar to his own unique tune. #



Brody Levesque is a veteran journalist & currently the Chief Political Correspondent for The New Civil Rights Movement Web Magazine and the former Washington Bureau Chief for LGBTQ Nation magazine.



Additionally an amateur historian, he published his first book on early U.S. presidential automotive transportation in 2015 and is working on his second book detailing the rise of a closeted gay American religious figure in the early to mid-twentieth century. He lives and works in New York City.



Photography courtesy of Jaimie Wilson