Gary was born in Framingham, Massachusetts, the youngest of three brothers. He was a competitive swimmer and diver through his early teens. After graduating high school, Gary went to Johnson & Wales to study culinary arts, and then on to Emerson College, Boston, MA, where he graduated with a degree in film, TV, theatre and creative writing. While in college he worked as lighting designer for local rock bands including "til Tuesday and "The Fools." After graduation, Gary moved to Los Angeles to pursue acting and screenwriting.