Emerson's first big role was in 1997. He starred as Oscar Wilde in Moises Kaufman's play, "Gross Indecency: The Trials of Oscar Wilde," and then was in many other plays. In 1998, he acted with Uma Thurman in the off-Broadway production of "The Misanthrope". In 1999, he played the part of Willie Oban in "The Iceman Cometh" with Kevin Spacey. He co-starred with Kate Burton in both "Give Me Your Answer, Do!" and "Hedda Gabler".