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Singer Duets With His Past Self
28 May
Summary
- Singer performs duets with his former self using old recordings.
- This project is seen as cathartic and healing for the artist.
- He embraces all versions of himself as part of an evolution.

British singer-songwriter Dylan Holloway, known as Dylan and the Moon, has found a unique way to express his gender transition through music. He creates "trans duets," where he performs alongside older recordings of himself singing in his former voice.
Holloway, who first came out as transgender at age 26, initially considered distancing himself from his past. However, encouraged by his mother, he kept old recordings, which later proved invaluable for his healing process.
The experience of hearing his past and present voices together was profoundly moving for Holloway, bringing him immense compassion for his former self. He views his journey not as leaving a past person behind, but as an evolution.
He gained recognition in England as a contestant on "X Factor" and will embark on a UK tour in November, with plans to release an album of trans duets. Holloway's approach has been met with positive reactions from the transgender community.
Transitioning presented challenges, particularly concerning his voice. Testosterone therapy significantly altered his vocal range and quality, causing initial distress and canceled performances. After about a year and a half on testosterone, his voice settled, and he has since worked to regain his previous vocal range and expand his new lower notes.
Holloway's artistic journey is also documented in the upcoming 2025 documentary "Tomorrow's Too Late."