British singer-songwriter Dylan Holloway, who performs as Dylan and the Moon, has been wowing audiences with his voice for quite some time. But what makes Holloway especially unique is that he also charmed crowds before identifying as male. While Holloway had long wrestled with his gender identity, he transitioned from female to male during the COVID-19 pandemic. While some might say they never look back, Holloway chooses to look back with love and gratitude for his former self. In a recent clip posted to Holloway’s Instagram page, he shows his followers a split screen. On the left is Dylan presenting as female, with blonde curls and soprano notes. That side is labeled “2018.” On the right is modern-day Dylan, now presenting as male, shirtless and tattooed, marked “2026.” To the song “Kiss Me,” he harmonizes with his former self, and it’s absolutely pitch-perfect. View this post on Instagram “A duet with my past self” At the top of the clip, he writes, “Singing with my past self…trans duet.” Holloway adds in the comments: “A duet with my past self. I make these videos because it brings me joy to embrace my entire journey & it helps me spread love to others who may wish to do the same… I’m proud of who I am & the unique art I can make because of it … whoever you are, whatever your journey, you are wonderful & deserve love for your whole self too.” Fans in the comment section were equally loving and seemingly in awe: “You were and are a beautiful person, with a lot of charisma, musically and a beautiful voice. In both interpretations. Gifted! I’m impressed.” “I see a talented musician who is proud of his story and who loves himself, as he should.” Sixpence None the Richer As for the song? The year was 1998. The band Sixpence None the Richer had taken American radio stations by storm with their sweet, melodic single “Kiss Me” from their self-titled album, released a year earlier. Its lyrics are pretty straightforward, though some could call them a tad bossy. The singer would like a gentleman to kiss her “behind the bearded barley. Nightly, behind the green, green grass. Swing, swing. Swing the spinning step. You’ll wear those shoes and I will wear that dress.” Holloway nails every note. @dylanandthemoon The X Factor (lol) 11 years & 1 transition later #xfactor #transition #transgender #transman before and after ♬ original sound – DylanAndTheMoon Obvious X Factor Back in 2012, Holloway became a sensation while competing on Britain’s The X Factor, where he ended up as a finalist in a band called MK1. More recently, he compiled clips from the show featuring his former self singing beautifully then and just as purely now as a man. In an interview with DIVA Magazine, Holloway described his time on the show: “MK1 ended up at the finals on national television, which was such a turning point in my life. Until then I had just been a little androgynous kid from Newquay with a secret inside me, and now I was a rapper in an urban band on telly. But everyone knew me as someone I wasn’t, and I felt like a caricature of myself. Eventually, after a few years, these feelings bubbled to the surface and I couldn’t continue to be this person everyone thought I was, so I drifted and started releasing my own music under the name Lots Holloway.” View this post on Instagram Compassion and love When asked what it’s like singing with his former self, Holloway seemed to feel at peace: “It’s actually such a wonderful experience to look at them now. I think a lot of transgender people find there’s a pressure, whether they put that on themselves or it is external pressure, to eliminate the person you once were when you become someone new. Now I’m the person I am today, I look back at old footage of myself with this new compassion and love. I wouldn’t be here right now if it wasn’t for that brave, resilient, and bold soul that was brave enough to come out.” Alongside his career as a musician, Holloway also speaks professionally about mental health advocacy and LGBTQ rights. On the Raise the Bar website, where he is listed as one of its motivational speakers, the organization shares the importance of these side-by-side videos: “In posting these videos, he spreads the message that it is okay to accept your old self, as it is all part of the journey that makes you who you are now.” Upworthy spoke with Holloway, who shared how he feels about transitioning and music in general. “For awhile, I thought I had to leave that version of myself behind. But over time, I realised there was something really beautiful about letting both versions of me exist together,” he said. “So instead of erasing my past, I started creating duets with old vocal recordings and videos I had. Almost like having a conversation across time with younger me. So healing. How many people ever have that opportunity? I want other people to know it’s okay to embrace who you are – the whole story.” He says his favorite duet so far is “Yellow” by Coldplay. “This song came out when I was growing up and confused about myself,” he said. “I recorded it on a rooftop in 2018. Then went back to the same place in 2026 to film again, totally free and transitioned. And the merging of those two people together, to me, is beautiful. I love how the lyrics mean something totally different in this context. ‘Your skin and bones turn into something beautiful. I swam across. I jumped across for you. You know I love you so.’ All of it.” He added, “My dream is that Coldplay will see it and see how much their song helped heal me. And one day, we will play it together with the old version of me projected behind us to sing it too. In a huge stadium, of course. I want to spread the message of acceptance and love as far as we can.” “Traditional songwriting” is where he draws most of his influence: “People who tell stories. People who write to move others. Dolly Parton, David Bowie, Coldplay, Paul Simon, Tracy Chapman. Iconic.” He plans to keep telling those stories. “I’m a totally independent artist, and this year, I’m creating an album in public and allowing my fans to make decisions along the way,” he said. “I make one bit of content a day and release one song a month. Eventually, it will all come together into an album. And my fans will know they helped bring it to life. So everyone is welcome to come and get involved!” Holloway is also releasing a documentary later this year that shares more of his story. “It shows an up close and personal journey of my transition from the lens of being a singer who risked losing their voice,” he said. The post A trans man beautifully harmonizes to the song ‘Kiss Me’ alongside a 2018 clip of himself appeared first on Upworthy.