Freeman was born in Chicago His father is Jewish. He is the oldest of three children. His sister, Cassidy Freeman is an actress, while his brother Clark is an actor and musician. Freeman graduated from the Latin School of Chicago in 1990 and earned a BA from Williams College, where he majored in theater and minored in computer science. He then earned an MFA in acting from Columbia University and went on to perform on Broadway, at the American Repertory Theater, at the Mark Taper Forum, at Cincinnati's Playhouse in the Park, and at the Williamstown Theater Festival. As a child, he was greatly influenced by anime such as Speed Racer and Battle of the Planets. Casey Kasem voiced the role of his favorite character, Mark of Battle of the Planets, and Freeman even wanted to change his name to Mark at one point. He later discovered Voltron, Star Blazers, and Robotech. He has also stated that the reason he got into the industry was because of the anime The Vision of Escaflowne. He initially got involved in the voice-over industry when a friend of his landed a role in Peacock King.
Knowing Freeman was a big anime fan, a friend suggested he call up Central Park Media (CPM) and apply for a job doing English dubs. When originally approached about dubbing, he initially declined. It was not until he remembered all of the anime shows he watched as a child that he realized that many people are introduced to anime through the English dubbed versions. In 1997, Freeman landed the role of Zelgadis Graywords in Slayers along with Lisa Ortiz, Eric Stuart and Veronica Taylor. He was the second and final voice actor to get the job, after Zelgadis' original voice actor, Daniel Cronin, lost contact with CPM after a year-long halt in the dubbing. Years later he turned to the American animation voice acting grounds.
Freeman has been best known for his work in Marvel Comics based productions such as The Spectacular Spider-Man, Wolverine and the X-Men and The Avengers: Earth's Mightiest Heroes. He then starred as several versions of Roy Harper in Young Justice for DC Comics and Warner Bros. Since then, Freeman has had various roles throughout his career. He has appeared in many video game titles as memorable characters, such as Albedo from Namco's Xenosaga series, the god of the sun Helios in God of War III, Haji, Joel the 6th and Van Argeno in Blood+, the main protagonist Baldur in Silicon Knights's Too Human, Breakdown in Transformers: War for Cybertron, the Winter Soldier in Marvel: Ultimate Alliance, and Iron Man in Marvel: Ultimate Alliance 2.

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