Season Regulars 1

1. Kalief Browder

   Self

Guest Stars 39

1. 

   Jay-Z

   Self

2. 

   Josh Rhett Noble

   Public Defender

3. Donnell E. Smith

   Kalief Browder

4. Harry Bass

   Self (former Rikers' CO)

5. 

   Preet Bharara

   Self (US Attorney)

6. Jacqueline Brantley

   Self (Acting Warden at Rikers)

7. Turray Bynum

   Self (Former Rikers' inmate)

8. 

   Bill de Blasio

   Self

9. Florence Finkle

   Self (Former Commissioner, NYC Department of Corrections)

10. Gary Hayward

    Self (former Riker's CO)

11. Ira Judelson

    Self (Celebrity Bail Bondsman)

12. Jacob Morris

    Self (Historian)

13. Ken Pawlukliewicz

    Self (former Rikers' CO)

14. Dora Schriro

    Self (former Commissioner, NYC Department of Corrections)

15. 

    Al Sharpton

    Self

16. Bill Sheridan

    Self (gang expert)

17. Keenan Telemaque

    Self (former Rikers' inmate)

18. Erica Matos

    Nicole Browder

19. Darryl Bryant

    Self (former Rikers' CO)

20. Jhonathan Valencia

    Roberto Bautista

21. Mary Buser

    Self (Former Assistant Medical Health Chief)

22. Ismael Nazario

    Self (prison reform advocate)

23. Tyrone Pennington

    Self (Kalief's friend)

24. Akeem Browder

    Self

25. Deion Browder

    Self

26. Kamal Browder

    Self

27. Raheem Browder

    Self

28. Nicole Browder

    Self

29. Jeff Robinson

    Self (ACLU)

30. Venida Browder

    Self

31. 

    Van Jones

    Self

32. Paul Prestia

    Self (lawyer)

33. Alex Vitale

    Self (Criminal Justice Expert)

34. Dashaun Jiwe Morris

    Self

35. Donna Lieberman

    Self (New York Civil Liberties Union)

36. Michael Schwirtz

    Self

37. Liana Bedgood

    Self (Kalief's friend)

38. Michael Winerip

    Self

39. 

    Adriana DeMeo

    City Attorney (voice)

Crew 4