🔵 The new single “Tear In Your Hand" by queer artist Gregory Douglass

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or most of his career, Gregory Douglass has existed just outside the machinery of the music industry.

Long before the modern wave of independent artists building careers online, Douglass was already doing it the hard way: writing songs alone at the piano, releasing records independently, touring relentlessly, performing house concerts, funding his music through fan support, and building a devoted audience one listener at a time.

NPR’s Morning Edition once called him “one of New England’s best-kept secrets,” while OUT Magazine praised the way his music blends “Rufus Wainwright’s opulent musicality and Justin Timberlake’s accessible soulfulness.”

But Douglass never quite fit the traditional mold of a singer-songwriter career. Not because he lacked the voice – critics have praised its striking emotional depth for years – but because he refused to shape his work around industry expectations.

Instead, he let the music pave the way.

Over the course of a 25-year career, Douglass has independently released ten studio albums, collaborated with international producers, and shared stages with artists including Grace Potter, Jason Mraz, Regina Spektor, Patty Griffin, They Might Be Giants, and fellow Vermont collaborator Anaïs Mitchell (Hadestown). In 2019, his song “Alibis” appeared in the Netflix series The Rain, quietly introducing his music to a growing international audience.

• And somewhere along the way, his relationship with music had changed too.

And yet the deeper story of Gregory Douglass isn’t about success or obscurity. It’s about endurance.

After more than a decade of touring and releasing music at a relentless pace, Douglass stepped away from the cycle he had built. The industry had changed. The definition of success had changed. And somewhere along the way, his relationship with music had changed too.

“I realized I’d spent years trying to prove something,” he says. “At some point you have to ask yourself who you’re actually making the music for.”

The answer eventually became AMATEUR.

His forthcoming eleventh album marks Douglass’ first major body of original work in nearly a decade, and it arrives not as a comeback record but as something far more vulnerable: a sort of reckoning.

Built around piano, voice, strings, and bass, AMATEUR strips away the gloss of modern production to focus on the emotional core of the songwriting. The result is a deeply intimate chamber-pop album that explores queer identity, open relationships, childhood memory, artistic survival, and the complicated process of learning to love oneself again.

Much of the album was shaped by Douglass’ life over the past several years living in Palm Springs, California – a place where queer culture, sexuality, and community coexist in ways that forced him to confront long-held ideas about love, shame, and authenticity.

• I was drawn to the song for the way it holds intimacy

“Life has a way of revealing you,” Douglass suggests. “Just when you think you’ve got it figured out, everything changes. The more life you live, the more you realize how little you actually understand. That feeling of always learning – and always getting back to the core of things – is what AMATEUR is about.”

Across the album, Douglass examines the emotional architecture of modern queer life with startling candor.

His new single “Tear in Your Hand" is an interpretation of one of the most  emotionally complex Tori Amos songs from Little Earthquakes. Douglass confides, "This version honors the woman who taught me how to write songs that matter. It’s a song I’ve turned to in every major life transition – a breakup anthem for letting go of the familiar and stepping into the unknown. “Tear in Your Hand” is my first-ever recorded cover of a Tori Amos song, despite her being one of the most formative influences on my voice, songwriting and musical identity. I was drawn to the song for the way it holds intimacy, heartbreak and emotional ambiguity at once, and approached it as a deeply personal interpretation through my own voice. It’s the second single from AMATEUR – my first original album in roughly a decade and, in many ways, the most Tori-influenced record I’ve made."

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Appropriately, the album itself will unfold slowly. Rather than dropping the project all at once, Douglass plans to release a series of singles throughout 2026, allowing listeners to experience the record the way it was written – as a gradual emotional journey – before the full album arrives in November, 2026.

This strategy mirrors the philosophy that has defined his career from the beginning: patience, independence, and trust in the long arc of the work.

• I learned the real reward is learning how to love

“Like so many others, most of my career has been motivated by the idea of success,” Douglass says. “But somewhere along the way I learned the real reward is learning how to love what you’ve already created and who you’ve become through creating it.”

With AMATEUR, Gregory Douglass returns not as the artist he once hoped to be, but as the artist he’s always been. And he may have arrived at the most powerful place an artist can reach: the courage to begin again.

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