Drew Deprey is a singer-songwriter and performer from the Northern Greater Boston area, whose path has run from major label stages to Nashville writing rooms and back home to the New England bars and stages where he first learned his craft.

Born in Concord, New Hampshire and raised in Billerica, Massachusetts, Drew came up through the Boston music scene before signing with Roadrunner Records (Warner Music Group) as the lead singer and co-writer of the rock band, Stilrize. The label years put him on big stages, in professional studios, and shoulder to shoulder with some of the most accomplished writers and producers in the business.

From there, Nashville. Drew spent years writing in rooms alongside major label artists and hit songwriters across rock and country, sharpening a craft built on story first songwriting: specific, honest, working class language delivered with earned emotion. Those years shaped everything about how he writes and performs today.

But New England kept calling. Drew returned home to Massachusetts to place roots for his young family, and went back to doing what he has always done best: performing live, week after week, for the people in the room. His weekly residency has packed the same rooms for years, a rare feat in any market, built on up to three-hour performances, a repertoire of music spanning six decades, and a connection with audiences that cannot be faked.

Today, Drew performs throughout New England and beyond, from private and corporate events to community stages, bringing a professional, fully self-contained show wherever he goes. His original music draws comparisons to the raw, lived-in songwriting of artists like Chris Stapleton, Jason Isbell, and Zach Bryan, and his catalog continues to grow with new releases under his own name.

For select events, Drew offers something few performers can: an original custom song, written from your stories by a Nashville trained songwriter, and premiered live in the room for the person it honors.

Life is full of journeys and memories. Songs capture them forever.