In 1999, Esparza played Che in the national tour of "Evita", opposite Natalie Toro. The tour was intended to open on Broadway, but failed to do so. In 2001, he appeared Off-Broadway in "tick, tick... BOOM!" by Jonathan Larson, garnering a Drama Desk Award nomination for Outstanding Actor in a Musical. He appeared in two musicals by Stephen Sondheim, "Sunday in the Park with George" and "Merrily We Roll Along" at the 2002 Kennedy Center Sondheim Celebration. He also appeared as the Arbiter in the Actors Fund of America concert of Tim Rice's "Chess" in September 2003.