In 2008, after completing a run of the awardwinning production of Dennis DeYoung’s The Hunchback of Notre Dame in Chicago, he returned to Los Angeles to perform in Jacques Brel: A Life in Song (Best Cabaret Ensemble Ticket Holder Award), translated and directed by Peter Mellencamp. Chicago theatre highlights include Galileo (Goodman Theatre), Kabuki Medea (Wisdom Bridge), Chicago and Grant Park Symphonies as a vocalist, and Ensemble Espaņol as a company dancer.
Other recent southern California credits include Glengarry Glen Ross (Egyptian), Twentieth Century (Lillian Theatre), Wild About Harry (Crown City Theatre), The Winter’s Tale (A Noise Within), Man of La Mancha (A Noise Within, Best Supporting Actor Ticket Holder Award), Joan of Arc (The Lobero), and The Boys From Syracuse (Crown City Theatre, Garland Citation).
Additional theatres include Actors Alley, Actor’s Company, Long Beach Studio, Welk Resort, Southern Arizona Light Opera, California Music Theatre Broadway Series, Jewel Box, Theatre Geo, Inside The Ford, Ark, and Whitefire.
In 2005, Gregory performed at the Edinburgh Fringe Festival under producer Jon Lawrence Rivera and continues to tour with The Roger Wagner Chorale to Japan. He has been a recurring sketch player for Talk Show With Spike Feresten.
Other screen credits include House, Mad Men, Samantha Who?, Close To Home, Ghost Hunters: Point of Contact, Friendly Fire, Pure Love, and Power Poison.