Greg was born in Falls Church Virginia, but his family moved to Lewiston, Maine, when he was six years old.He started acting in school plays in middle school then became an active member, eventually president, of his high school drama club. In high school he was also involved with the debate and speech teams, the mock trial team, and for a short while the math team.Greg attended the University of Chicago, where he became more and more seriously involved in the theater. After a stint with the comedy troup Off-Off Campus, he directed or acted in numerous shows. He received a B.A. in Philosophy in June, 2004, graduating with multiple honors.
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