Drew Gregory

Get ready for an unforgettable live country experience packed with nostalgia, high-energy performances, and the songs you know and love. Drew is incorporating a ’90s theme throughout his live sets, creating a high-energy experience that celebrates the era’s biggest country hits while putting his own modern spin on the sound. Backed by a powerhouse band, Drew delivers a show packed with the most recognizable country songs of the ’90s, infused with his own hit songs and signature sound. It’s the perfect blend of nostalgia and fresh country—giving audiences the songs they know and love while showcasing an artist with a growing catalog of original music. From the opening note to the final encore, Drew knows how to work a crowd. Expect big vocals, sing-alongs, dancing, Nashville energy, and a feel-good atmosphere that keeps audiences engaged from start to finish. The ’90s theme adds an extra layer of nostalgia and fun, taking audiences back to one of country music’s most memorable eras while keeping the show fresh, current, and uniquely Drew. Perfect for festivals, casinos, fairs, theaters, corporate events, and concert venues, Drew Gregory delivers a show built to entertain, connect, and leave audiences wanting more. Throughout his career, Drew has shared the stage with artists including Owen Riegling, Paul Brandt, Cody Johnson, Tenille Townes, The Reklaws, and Jade Eagleson. His energetic live performances have appeared on some of North America’s biggest country music stages, including Big Valley Jamboree, Country Thunder Calgary and Arizona, Calgary Stampede’s Nashville North, and Dauphin’s Countryfest, to name a few.