| Melina Abdullah | | Self - Interviewee |
| Michelle Alexander | | Self - Interviewee |
| Cory Booker | | Self - Interviewee |
| Dolores Canales | | Self - Interviewee |
| Gina Clayton | | Self - Interviewee |
| Gina Clayton | | Self - Attorney and Founder, Essie Justice Group |
| Jelani Cobb | | Self - Interviewee |
| Malkia Cyril | | Self - Interviewee |
| Angela Davis | | Self - Interviewee |
| Craig DeRoche | | Self - Interviewee |
| David Dinkins | | Self - Interviewee |
| Baz Dreisinger | | Self - Interviewee |
| Kevin Gannon | | Self - Interviewee |
| Henry Louis Gates Jr. | | Self - Professor of History, Harvard University |
| Marie Gottschalk | | Self - Professor of Political Science, University of Pennsylvania |
| Newt Gingrich | | Self - 50th Speaker of the House of Representatives, 2012 Republican Presidential Candidate |
| Lisa Graves | | Self - Executive Director, Center for Media and Democracy |
| Cory Greene | | Self - Formerly Incarcerated Activist / Co-Founder, H.O.L.L.A. |
| John Hagan | | Self - Professor of Sociology and Law, Northwestern University |
| Michael Hough | | Self - Maryland State Senator (R), American Legislative Exchange Council (ALEC) |
| Van Jones | | Self - Founder, #CUT50 / Founder & President, Dream Corps |
| David Keene | | Self - Chairman 1984 - 2011, American Conservative Union |
| James Kilgore | | Self - Formerly Incarcerated Author, Understanding Mass Incarceration |
| Glenn E. Martin | | Self - Formerly Incarcerated Activist / Founder, JustLeadershipUSA |
| Marc Mauer | | Self - Executive Director, Sentencing Project |
| Khalil Gibran Muhammad | | Self - Professor of History, Race and Public Policy, Harvard University |
| Pat Nolan | | Self - Formerly Incarcerated Activist / SVP, Prison Fellowship |
| Grover Norquist | | Self - Board Member, Americans for Tax Reform |
| Dorsey Nunn | | Self - Executive Director, Legal Services for Prisoners with Children |
| Liza Jessie Peterson | | Self - Incarceration Activist and Educator |
| Charles Rangel | | Self - Congressman (D), New York 13th District |
| Kyung-Ji Rhee | | Self - Center for Nu Leadership on Urban Solutions |
| Rashad Robinson | | Self - Color for Change |
| Shaka Senghor | | Self - Formerly Incarcerated Activist / Director of Strategy, #CUT50 |
| Bob Sloan | | Self - Independent Investigative Journalist |
| Deborah Small | | Self - Attorney and Founder, Break the Chains |
| Bryan Stevenson | | Self - Attorney and Author / Founder, Equal Justice Initiative |
| Ken Thompson | | Self - District Attorney - Brooklyn, New York |
| Nicholas Turner | | Self - President, Vera Institute of Justice |
| Daniel Wagner | | Self - Investigative Reporter, Buzzfeed |
| Joe Atkins | | Self - Minnesota (DFL) (archive footage) |