Jay-Z
Self (6 eps)
Kalief Browder
Self (6 eps)
Venida Browder
Self (6 eps)
Van Jones
Self (6 eps)
Paul Prestia
Self (lawyer) (6 eps)
Adriana DeMeo
City Attorney (voice) (6 eps)
Akeem Browder
Self (5 eps)
Nicole Browder
Self (5 eps)
Jeff Robinson
Self (ACLU) (5 eps)
Deion Browder
Self (4 eps)
Kamal Browder
Self (4 eps)
Raheem Browder
Self (4 eps)
Michelle Alexander
Self (4 eps)
Donna Lieberman
Self (New York Civil Liberties Union) (4 eps)
Robin Steinberg
Self (The Bronx Defenders) (4 eps)
Darryl Bryant
Self (former Rikers' CO) (3 eps)
Mary Buser
Self (Former Assistant Medical Health Chief) (3 eps)
Samuel Gregory
Self (Defence Attorney) (3 eps)
Ismael Nazario
Self (prison reform advocate) (3 eps)
Tyrone Pennington
Self (Kalief's friend) (3 eps)
Eric Holder
Self (former US Attorney General) (3 eps)
Alex Vitale
Self (Criminal Justice Expert) (3 eps)
Shaun King
Self (3 eps)
Michael Schwirtz
Self (3 eps)
Liana Bedgood
Self (Kalief's friend) (3 eps)
Michael Winerip
Self (3 eps)
Stuart Grassian
Self (clinical psychiatrist) (2 eps)
Kenneth Montgomery
Self (Defence Attorney) (2 eps)
David Saverino
Self (Kalief's friend) (2 eps)
Mark Bodrick
Self (councillor) (2 eps)
Rosie O'Donnell
Self (2 eps)
Elizabeth Payamps
Self (advisor) (2 eps)
Frida Marte
Self (councillor) (2 eps)
Ritchie Torres
Self (NYC councillor) (2 eps)
James Meyerson
Self (Civil Rights Attorney) (2 eps)
Dashaun Jiwe Morris
Self (2 eps)
John Meehan
Self (Civil Rights Attorney) (2 eps)
Daniel Selling
Self (former Executive Director of Mental Health) (2 eps)
Charlene Alves
Self (Teacher) (1 eps)
Michael Braverman
Self (Civil Rights Attorney) (1 eps)
Andrew Morgan
Self (Social Worker) (1 eps)
James Nuciforo
Self (Former NYPD Detective) (1 eps)
Brendan O'Meara
Self (Public Defender) (1 eps)
Reynaldo Rivas Rios
Self (Bail Bondsman) (1 eps)
Ezra Ritchin
Self (Bronx Freedom Fund) (1 eps)
Gregg Stankewicz
Self (Lawyer) (1 eps)
Sade Thompson
Self (Bail Bondsman) (1 eps)
Kimberly Hardy Watson
Self (Former Foster Care Caseworker) (1 eps)
Harry Bass
Self (former Rikers' CO) (1 eps)
Preet Bharara
Self (US Attorney) (1 eps)
Jacqueline Brantley
Self (Acting Warden at Rikers) (1 eps)
Turray Bynum
Self (Former Rikers' inmate) (1 eps)
Bill de Blasio
Self (1 eps)
Florence Finkle
Self (Former Commissioner, NYC Department of Corrections) (1 eps)
Gary Hayward
Self (former Riker's CO) (1 eps)
Ira Judelson
Self (Celebrity Bail Bondsman) (1 eps)
Jacob Morris
Self (Historian) (1 eps)
Ken Pawlukliewicz
Self (former Rikers' CO) (1 eps)
Dora Schriro
Self (former Commissioner, NYC Department of Corrections) (1 eps)
Al Sharpton
Self (1 eps)
Bill Sheridan
Self (gang expert) (1 eps)
Keenan Telemaque
Self (former Rikers' inmate) (1 eps)
Erica Matos
Nicole Browder (1 eps)
Shamel Peterson
Self (Kalief's friend) (1 eps)
Alex Dranovsky
Self (Professor of Clinical Psychology) (1 eps)
Jhonathan Valencia
Roberto Bautista (1 eps)
Scott Levy
Self (1 eps)
Peter Moskos
Self (former NYPD detective) (1 eps)
Stanley Richards
Self (Fortune Society) (1 eps)
Shira Scheindlin
Self (former judge) (1 eps)
Daniel Squadron
Self (1 eps)
Michael Caines
Self (former Rikers' inmate) (1 eps)
Jason Davis
Self (former Rikers' inmate) (1 eps)
Marc Lamont Hill
Self (1 eps)
Jesse Spiegel
Self (Rewilding Program) (1 eps)
Doreen St. Felix
Self (1 eps)
Eddie Browder
Self (1 eps)
Sanford Rubenstein
Self (attorney) (1 eps)
Jeff Robinson
Self (ACLU) (1 eps)
Michael Johnson
Self (exonoree) (1 eps)
Victor Perez
Self (former Rikers' inmate) (1 eps)