His production of My Fair Lady played both the McCarter Theatre and Hartford Stage in 2004 after its debut at Chicago's Court Theatre.[14] In 2009 he directed a lauded production of West Side Story at the Stratford Festival of Canada. The reviewer for The Globe and Mail wrote: "Griffin's production has an electric charge that keeps the hairs on your skin tingling from start to finish, thanks to two incredible leads cast as the star-crossed lovers Tony and Maria and Rick Fox's assertive musical direction."[15]
Griffin has directed several Stephen Sondheim musicals for Chicago Shakespeare Theater, including A Little Night Music in 2003[16] and Sunday in the Park with George in 2012.[17] In 2014, he directed Road Show and Gypsy for CST.[13][18] 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.[19] 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."[20]