True-Frost graduated from New Trier High School in Winnetka, Illinois. He has been an ensemble member of the Steppenwolf Theatre Company in Chicago since 1989. Prior to that, he was a member of Remains Theater, co-founded by actor William L. Petersen (To Live and Die in L.A., CSI: Crime Scene Investigation). True-Frost appeared in the film Off the Map with fellow Steppenwolf ensemble member Joan Allen, directed by Singles co-star Campbell Scott. He has performed on Broadway and as far away as Sierra Leone.