Born and raised in Toronto, Canada, Woodley began making films at the age of seven, studying the techniques of animation at the Art Gallery of Ontario. After graduating from York University's Film Production Department, Woodley worked in the industry as a film and television editor (receiving two Gemini nominations), a television writer and stop-motion animator. He also wrote and directed the award-winning short films Pipe Dreams (1994), The Wager (1998), Bed & Breakfast (2000) and Downpour (2000). His feature film debut, Rhinoceros Eyes, starring Michael Pitt (The Dreamers, Funny Games), won the Discovery Award at the 2003 Toronto International Film Festival. His follow-up was Tennessee, produced by Lee Daniels (Monster's Ball, Precious) and starring Adam Rothenberg, Ethan Peck and Mariah Carey. Woodley was one of four filmmakers involved in Toronto Stories, which made its debut at the Toronto International Film Festival.