Gregory Douglass '99 Talks Life and Music with Craig Gemmell

Nancy Hughes

May 7 2019

In his most recent episode of “Diverse Thinkers” podcast, Head of School Craig Gemmell talks with the Los Angeles-based singer-songwriter and performer Gregory Douglass ’99 about following one’s passion, serendipitous timing, life in California, and maintaining positivity in what can seem like challenging times. Upon graduating from Brewster, Douglass took the brave step of directly entering the work force, and he credits Brewster with setting the stage for his ambitious and successful entrance into the world of professional songwriting and performing. Douglas explains:

“I left campus feeling so inspired and motivated to just make it happen, and in 1999 the time was prime for singer-songwriters to do it themselves, and I did just that. I didn’t want to wait around to be discovered. I wanted to make it happen. Little did I know that this default way of doing things would become the norm.”

Douglass’s commitment to pursuing his passion as he finished high school led him to be ahead of the curve in an industry starting to be shaped by independent artists—aided by the rise of YouTube, crowdfunding, and livestreaming. Gregory now finds himself one of the top independent artists on Pandora radio. He has sold 200,000 plus songs digitally on his own, and his videos have gained more than a million views on his YouTube channels. And last spring his 2005 song “Alibis” was featured in Netflix’s original show “The Rain.” In the past 20 years, both artists and audiences have—through the advances in technology—changed how they produce and consume music, and Douglass acknowledges that he had a headstart taking advantage of these changes entering the business when he did in the late ’90s.

Dubbed “one of New England’s best kept-secrets” by NPR’s Morning Edition, Douglass, a Vermont native, reflects on his experience moving to and living in California in his discussion with Gemmell. As our Head of School admits to be being a bit overwhelmed by the pace and unrelenting stimuli of Los Angeles, Douglass explains how he steadily came to feel a part of a place that he now understands to be characterized by a devotion to family and creativity. “Everything exists here in Culver City …This is America,” Douglass explained, noting that too often we let our fears inhibit us from seeing people and places clearly. Being in this environment has allowed Douglass to evolve as a creative entrepreneur; he is making experimental music, scoring a musical, touring, and working with fellow artists to build a sustainable future for independent musicians. And after 20 plus years in the industry, he is confident about his journey and delighted to see that the central themes of his first album “If I Were a Man” (1998) are still alive in his new work, yet framed with a greater depth and sense of hope. For Douglass, music is a form of “light work,” part of the progress, which he thinks is inevitable. He explains: “I have learned to put the tragic into perspective. I am conscious of what the media is pushing us to consume.” And he pushes back. Despite what the news cycle suggests each day, Douglass says, “This is really a fortunate time for us to be living; this is a time of spiritual evolution. We are laying the groundwork for the future.”

In Douglass’s mind, that future is one that sees all experience as educational, that relishes diversity, and that allows individuals to honor their emotions fully—in music and in life. He offers that the diversity, which greeted him at Brewster, inspired him intellectually and creatively, and his journey inspires us with its optimism. We look forward to welcoming Douglass back to campus to share his perspective with current students in the 2019-20 school year.

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