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Critics called Gregory "spot on" in God of Carnage at Northern Stage.

Gregory plays a Wall Street exec who gets into a bar fight with James Caviezel in Person of Interest, the CBS action/crime series from JJ Abrams.

Gregory plays the all-American dad of a family desperate for a good vacation in this series of comedy spots.  

Gregory played Larry Bird in Magic/Bird, a new Broadway play about the rivalry and friendship of Magic Johnson and Larry Bird.  Hamilton's Tony-winning Thomas Kail directed.  (read reviews)

Gregory plays a Macy's security guard who screams like a little girl when Justin Bieber walks into the store for their Black Friday sale.

Gregory plays English bureaucrat Hector Sants in the critically-acclaimed HBO movie Too Big to Fail, starring William Hurt, Billy Crudup, Paul Giamiatti, James Woods, Topher Grace, Cynthia Nixon, and Tony Shalhoub.

Gregory appears in Episode 2 of the Comedy Central series, Onion SportsDome.

Originally aired in early 2010, SportsDome sends up sports media in American culture the way The Onion has been doing in its satirical newspaper and Web site for years.

In Episode 2, Gregory plays a tennis coach whose enthusiasm gets the better of him.

Stake Land, a vampire movie featuring Gregory, won the Audience Award for its category at the 2010 Toronto International Film Festival.  IFC, Dark Sky Films, and Glass Eye Pix distributed the film nationwide and on demand.  It is now available on DVD.

Gregory has been cast as General George Washington in the world premiere of Yorktown, a drama set during the climactic battle of the Revolutionary War.

Gregory wrote and performed in the May 2010 Thalia Follies with Broadway standouts like Chip Zien and Ivy Austin.