Gregory’s evocative, alternative sound blends "Rufus Wainwright ́s opulent musicality and Justin Timberlake ́s accessible soulfulness," (OUT Magazine). His recent spotlight on NPR's Morning Edition has coined him "one of New England's best- kept secrets." Douglass has shared the stage with artists like Regina Spektor, They Might Be Giants, Shawn Colvin, The Weepies, Jason Mraz, and Margaret Cho. According to Pandora's founder, Tim Westergren, Gregory is one of the top independent artists on Pandora radio today. Gregory has sold 100,000+ songs digitally on his own and his videos have amounted to over one million views on his YouTube channels. His music videos have also charted numerous times on MTV Network's LOGO TV.