Born in Chicago, Illinois, Crispin Freeman is the oldest of three children. He attended the Latin School of Chicago, where he graduated in 1990. He earned his Bachelor of Arts degree from Williams College, majoring in Theater and minoring in Computer Science. Afterward, he earned his Master of Fine Arts degree from Columbia University in Acting, and performed on Broadway (New York City), at the American Repertory Theater in (Cambridge), at the Mark Taper Forum in (Los Angeles), at Cincinnati's Playhouse in the Park, and at the Williamstown Theater Festival. As a child, Freeman was greatly influenced by anime shows such as Speed Racer and Battle of the Planets. Casey Kasem voiced the role of his favorite character, Mark of Battle of the Planets (he actually wanted to change his name to Mark at one point). Later, he discovered Voltron, Star Blazers, and Robotech, being quoted in the January 1999 issue of America Interview saying, "That show really blew me away." Freeman has also stated that the reason he got into the industry was because of the anime television show The Vision of Escaflowne. Freeman initially got involved in the anime voice-over industry when a friend of his landed a role in Peacock King.