In videos he posts across social media, British singer-songwriter Dylan Holloway performs duets with a younger musician, their voices intertwining seamlessly. Holloway knows his creative partner intimately. She is him, before he transitioned.

For these “trans duets,” as Holloway calls them, the 33-year-old indie-folk artist uses old recordings and videos to juxtapose his former self, playing guitar or piano and singing in a female voice, with footage of himself performing today, his vocals deepened by testosterone. Together, the two voices deliver both heartfelt original songs and covers, like Joni Mitchell’s wistful ballad “River” and “Yellow” from Coldplay . “Your skin and bones turn into something beautiful,” it goes.

“I sing duets with my old self because every version of me matters,” Holloway says. “I want people to know it’s OK to embrace who you’ve been. That person brought you here.”

Some who are transgender choose to leave their former selves behind once they transition to maintain distance from a time when they felt unseen, unsafe or disconnected from their true identity. Holloway, who performs under the name Dylan and the Moon, had the same inclination when he first came out to his family as transgender at 26.

“I thought I wanted to move forward and just be Dylan and move away from the past,” Holloway said over Zoom from his home in London. “No one will know I’m trans, and I’ll try and keep it a secret.” His mother, however, convinced her son to hold onto pieces of his former self, like his extensive old Spotify archive, in case he one day felt comfortable enough to revisit them.

Now he’s deeply grateful he followed his mom’s advice. The first time he listened to his past and present voices conversing musically, he burst into tears.

“It was incredibly cathartic and unfathomably healing,” he said. “It felt like healing grief in a strange way, being able to see someone you love again. I had this unbelievable compassion for this past version of myself that at one point I was going to throw away.”

Holloway, who is known in England as a former contestant on the reality TV music competition X-Factor , performs everywhere from intimate venues to music festivals and arenas. He’ll be touring the UK in November and plans to release an entire album of trans duets.

“So beautiful on so many levels beyond the music,” film director Shaun Peterson commented on one of the duets posted to Holloway’s Instagram account. “A gorgeous way to express transition, duality and identity.”

Music As Outlet And Lifeline

Growing up in a small town in southwest England, Holloway remembers feeling like a boy as early as 3 or 4. In a home video filmed on his sixth birthday, the little blond child with a missing front tooth opens a card his older sister addressed to her “youngest sister.” Looking into the camera, he quickly corrects the language.

“Youngest brother,” he insists.

As a teenager grappling with his identity and place in the world, he wrote songs to try to process the feelings of loneliness, fear and alienation he often suppressed.

“Music is the only thing that’s saved my life from going under,” he says in Tomorrow’s Too Late , a 2025 documentary about his musical journey and transition that’s currently showing at film festivals.

The artist went by Lots Holloway pre-transition and openly uses that name when sharing his story in the documentary and on Facebook, Instagram, TikTok and YouTube.

Because he views Lots not as a separate self, but as part of a continuous one, he avoids using the term “deadname.” It refers to the name a transgender person used before transitioning — for some, being referred to by it can feel like their current identity is being invalidated or disrespected.

Holloway, however, views the person he used to be as very much alive inside of him.

“That person isn’t dead to me,” he said. “It’s not a death. It’s an evolution.”

So far, fellow members of the transgender community have reacted with overwhelming positivity to the duets, Holloway said, and to his approach to his pre-transition self.

“There have been trans people who have said, ‘Wow, I love to see what you’re doing embracing your past,’” he said. “Mostly it’s been complimentary and inspirational vibes.”

Navigating A Changing Voice

The project emerged following unique transitioning challenges. As a musician, Holloway’s voice is inseparable from his identity and livelihood, and going on testosterone — which causes the vocal folds to thicken and lengthen, lowering pitch, while also enlarging the larynx — terrified him.

He wondered what he would ultimately sound like and whether people would still enjoy listening to him. About eight months into taking the hormone, which also increases muscle mass, causes body and facial hair to grow and impacts libido, he struggled to access notes, losing some altogether.

“It was like my range decreased from the top and the bottom,” he recalled. “It’s like any boy going through puberty when they get the squeaky voice and the kind of mismatch of sounds.” His voice sounded “pretty terrible,” he said. Suddenly, he couldn’t reach notes in songs he’d performed for years and canceled gigs.

He worried he was losing his singing voice and lived with constant uncertainty about when it would settle, or whether it ever would.

About a year and a half into taking testosterone, it did, to his immense relief and joy. Suddenly a voice he felt had lived inside him for years finally became audible. He refined it by consistently practicing scales and doing other vocal exercises, a commitment he likened it to being an athlete in training.

“Now I can say that my range has expanded past what I already had because I have this wealth of new low notes,” he said.

He’s also trained himself to be able to sing in the falsetto range he had before.

“Tonally it sounds a bit different, but the range has become increasingly there again,” he said.

Other transgender singers have spoken about the complexity of balancing their transitions with professional identities that depend on their voices. In a New York Times piece on trans opera singers, some talk about finding their new voices. Others share their decision to leave their voices alone were even while beginning to present differently.

As Holloway started to transition, he too considered leaving his voice untouched. But the elation he experienced as people began to see him as the man he’d always felt like inside outweighed any potential musical trade-offs.

“I was like, ‘I feel so good as a human being that I want to just keep going,’” he said. “I'm so glad I did.”