Guest Stars Gloria Reuben as Krista Gordon Sunita Mani as Shama "Trenton" Biswas Azhar Khan as Sunil "Mobley" Markesh Joey Bada$$ as Leon Michael Drayer as Francis "Cisco" Shaw Brian Stokes Mitchell as Scott Knowles Craig Robinson as Ray Heyworth Michele Hicks as Sharon Knowles Michael Maize as Lone Star Chris Conroy as Derek Don Sparks as Donald Moss Jeremy Bobb as Joseph Green Co Starring Annika Pergament as Herself Eve Lindley as Hot Carla Bernadette Quigley as Chaplain Sean Allan Krill as Kevin Budd Mishkin as Themselves Sean Patrick Folster as Hammerhead Lorin Partalis as Monica Danielle Nicolette Najarian as Prison Guard Keith Herron as Department Head #3 Susannah Schulman Rogers as Department Head #2 Peter Duncanson as Peter Spilkomen Ronan Babbitt as Surveillance Guy John Adams as FBI Agent Curzon Dobell as Department Head #1