Recurring guest stars included Adewale Akinnuoye-Agbaje as inmate and Homeboys gang leader Simon Adebisi, Rick Fox as inmate and former basketball star Jackson Vahue, goodfella Mike G as inmate and Schibetta's right-hand man Joey D'Angelo, Stephen Gevedon as biker inmate Scott Ross, Craig muMs Grant as inmate Arnold "Poet" Jackson, Željko Ivanek as Governor James Devlin, Tim McAdams as Homeboys inmate Johnny Post, George Morfogen as long-term inmate Bob Rebadow, Steve Ryan as corrupt Officer Mike Healy, Lauren Vélez as prison doctor Gloria Nathan, and J. D. Williams as Homeboys inmate Kenny Wangler.