- Anne-Sophie Mutter - Self - Guest
- Shelley Winters - Self - Guest
- Horton Foote - Self (Charlie Rose archive footage 4/3/97)
- Natasha Richardson - Self (Charlie Rose archive footage 8/15/05)
- John Hope Franklin - Self (Charlie Rose archive footage 12/1/05)
- Jack Kemp - Self (Charlie Rose archive footage 11/10/94)
- Ed McMahon - Self (Charlie Rose archive footage 4/14/98)
- Robert McNamara - Self (Charlie Rose archive footage 4/17/95)
- Walter Cronkite - Self (Charlie Rose archive footage 12/27/96)
- Frank McCourt - Self (Charlie Rose archive footage 12/30/97)
- Merce Cunningham - Self (Charlie Rose archive footage 4/6/95)
- Charles Gwathmey - Self (Charlie Rose archive footage 9/20/93)
- Les Paul - Self (Charlie Rose archive footage 11/27/91)
- Don Hewitt - Self (Charlie Rose archive footage 6/5/92)
- Ted Kennedy - Self (Charlie Rose archive footage 2/9/07)
- Dominick Dunne - Self (Charlie Rose archive footage 10/7/99)
- Larry Gelbart - Self (Charlie Rose archive footage 3/24/98)
- Thomas Hoving - Self (Charlie Rose archive footage 2/5/98)
- Ron Silver - Self (Charlie Rose archive footage 2/27/92)
- Miles Davis - Self (Archive footage)
- Jerry Nachman - Self (Editor, The New York Post)
- Robert Irving III - Self (Archive footage. Keyboards)
- Vince Wilburn Jr. - Self (Archive footage, Drums)
- Bob Berg - Self (Archive footage, Saxophones)
- Marilyn Mazur - Self (Archive footage, Percussion)
- Robben Ford - Self (Archive footage, Guitar)
- David Grubin - Self (Writer, Producer "LBJ")
- Lady Bird Johnson - Self (Archive footage)
- Lyndon B. Johnson - Self (Archive footage)
- C. Everett Koop - Self (Former U.S. Sugeron General)
- James Brown - Self (Archive footage)
- Janet Jackson - Self (Archive footage, Alright music video)
- Michael Kidd - Self (Archive footage)
- Wendy Wasserstein - Self (Playwright)
- Colin Moore - Self (Attorney)
- Avi Weiss - Self (Hebrew Institute of Riverdale)
- Alan Dershowitz - Self (Attorney)
- Calvin Trillin - Self (Author)
- Bill Moyers - Self (Archive footage, World of Ideas)
- Nadine Gordimer - Self (Archive footage, World of Ideas)
- Douglas Coupland - Self (Author)
- Robin Adler - Self (Co-Founder, "UN")
- Dan Rather - Self (CBS News)
- Mutang Urud - Self
- Tommy Tune - Self (Director, Choregrapher)
- Gregory Hines - Self (Archive footage)
- Mauricio Obregon - Self (Host, Columbus and the Age of Discovery)
- Shelby Steele - Self (Playwright)
- David Halberstam - Self (Author)
- R.W. Apple, Jr. - Self - Voice (The New York Times)
- Bella Abzug - Self (Former Congresswoman)
- Tony Brown - Self (Journalist)
- Terrence McNally - Self (Playwright)
- Al Pacino - Self (Archive footage, Frankie and Johnny)
- Bill Bradley - Self (Senator, New Jersey)
- Cornel West - Self (Professor, Princeton University)
- Jonathan Alter - Self - Senior Editor, Newsweek
- Richard Gere - Self - Chair, Tibet House New York
- Anita Hill - Self (Archive footage, Senate Confirmation Hearings 10/11/91)
- Clarence Thomas - Self (Archive footage, Senate Confirmation Hearings 10//11/91)
- Rush Limbaugh - Self (WABC-AM Talk Host)
- Raoul Felder - Self (Attorney for Robin Givens)
- Mario Cuomo - Self (Governor New York)
- Sam Roberts - Self (Columnist, The New York Times)
- Jimmy Breslin - Self (Columnist)
- Daniel Boulud - Self (Head Chef, Le Cirque)
- Hedrick Smith - Self (Author of "The New Russians")
- Bill Tatum - Self (Charlie Rose archive footage 1/20/92)
- Nancy Collins - Self (Vanity Fair)
- Robert D. Novak - Self (Charlie Rose archive footage 8/3/07)
- John E. Mack - Self
- Anthony Hopkins - Self
- Oren R. Lyons - Self
- Thomas Banyacya - Self
- William Commanda - Self
- Diplo - Self - Guest
- Kamasi Washington - Self - Guest
- Skrillex - Self - Guest
- Lin-Manuel Miranda - Self - Guest
- Leslie Odom Jr. - Self - Guest
- Thomas Kail - Self - Guest
- Robin Williams - Self - Guest
- Mark Romanek - Self - Guest
Al Pacino interpreta a Self (Archive footage, Frankie and Johnny) en la serie.
Richard Gere hace el papel de Self - Chair, Tibet House New York.
Charlie Rose interpreta a Self - Host en la serie.
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