Drew was born in Vancouver, British Columbia, Canada. His father, Philip Moss, was born in Calgary, Alberta, and found success in commercial real estate. His mother, JoAnne Peters, was born in Regina, Saskatchewan, and worked as a secretary until Drew was born. Drew moved to Toronto with his family in 1990. He began acting after graduating from Toronto Film School. Drew is also a graduate from Algonquin College for Aviation Management and is a fully licensed Commercial Pilot.