Some of his prominent anime roles include Zelgadis Graywords in Slayers, Kyon in The Melancholy of Haruhi Suzumiya, Togusa in the Ghost in the Shell franchise, Alucard in Hellsing, Kirei Kotomine in Fate/Zero and Fate/stay night: Unlimited Blade Works, Itachi Uchiha in Naruto, Gyomei Himejima in Demon Slayer: Kimetsu no Yaiba, Hagi in Blood+ and Shizuo Heiwajima in Durarara!!.

[3] 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.

[citation needed] 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.

In 1997, Freeman landed the role of Zelgadis Graywords in Slayers along with Lisa Ortiz, Eric Stuart and Veronica Taylor.

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.