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As a Miami native, Gregory first gained interest in an acting career while performing in plays during his senior year of High School. Then during his sophomore year in college, he decided to move to Los Angeles and pursue his acting career. It was there that he spent years training and honed his craft studying at various places, including with world renowned Stanislovski based teacher, Howard Fine and at the equally renowned Groundlings Theater. Groundlings were responsible for having shaped the comedic skills of such alumnus as Phil Hartman, Will Ferrell, Kristin Wiig, Jon Lovitz, Darrell Hammond, and several other notable performers on SNL. Throughout his career, Gregory has worked in Film, TV (including the lead in two sitcom pilots), several national commercials (Including Burger King, Colgate, Napa Auto Parts, Home Depot, Penske, and even a 1-800 COLLECT commercial where he was worked with (and cast by) Hollywood's acclaimed director, Barry Sonnenfeld), as well as several regional spots (Including Sun Sentinel, Georgia Lottery, and Fiesta Food Chains). Gregory also performed in various theatrical runs on both coasts.