Griffin has directed several Stephen Sondheim musicals for Chicago Shakespeare Theater, including "A Little Night Music" in 2003 and "Sunday in the Park with George" in 2012. In 2014, he directed "Road Show" and "Gypsy" for CST. Griffin has received eight Joseph Jefferson Awards for directing and has twice been named a "Chicagoan of the Year in the Arts" by the Chicago Tribune. He was the Co-Artistic Director of the Apple Tree Theatre in Highland Park, Illinois, starting in 1998, and was the artistic director of Drury Lane Oakbrook Terrace, Illinois starting in 1993. Regarding his work at Drury Lane Oakbrook Terrace, the "Chicago Tribune" wrote: "Gary Griffin is rapidly establishing himself as one of the most versatile--and busiest--directors on the local theater scene. As artistic director at Drury Lane Oakbrook Terrace, he has faithfully re-created an impressive roster of vintage musicals in recent seasons, while somehow finding time to moonlight in contemporary drama for such groups as Apple Tree, Pegasus Players and Buffalo Theatre Ensemble."