Barry has been an actor and lecturer at the Oregon Shakespeare Festival for 31 seasons, including dramaturging nearly 60 productions. Other acting credits include Colorado and Utah Shakespeare Festivals, Old Globe at San Diego, Berkeley Shakespeare Festival, San Jose Repertory Theatre, Shakespeare Santa Cruz, A Contemporary Theater in Seattle, American Conservatory Theater, and Marin Shakespeare Company, among others. He has acted in 88 full productions of all Shakespeare's 38 plays, more than 100 roles. Barry has written After Dinner Shakespeare and Shakespeare Insult Generator. He has recorded several books on tape, including Ovid’s Metamorphoses.