- Bill Russell - Self - NBA Hall of Famer
- Sam Smith - Self - Author
- Red Auerbach - Self (archive footage)
- Nelson George - Self - Writer & Filmmaker
- Kareem Abdul-Jabbar - Self (archive footage)
- Billy Crystal - Self - Entertainer
- Bill Walton - Self - NBA Hall of Famer
- Julius Erving - Self - NBA Hall of Famer
- Muhammad Ali - Self (archive footage)
- Jim Brown - Self (archive footage)
- Tommie Smith - Self (archive footage)
- John Carlos - Self (archive footage)
- Oscar Robertson - Self - NBA Hall of Famer
- David Stern - Self - Former NBA Commissioner
- Larry Bird - Self (archive footage)
- Magic Johnson - Self (archive footage)
- Grandmaster Flash - Self (archive footage)
- Sway Calloway - Self - Media Personality
- Metta Sandiford-Artest - Self - Former NBA Player
- Isiah Thomas - Self - NBA Hall of Famer
- Bill Laimbeer - Self - Former NBA Player
- Kendrick Lamar - Self - Musician
- Maverick Carter - Self - Businessman / LeBron's Manager
- Draymond Green - Self - NBA Player
- Kenny Smith - Self - Former NBA Player
- Justin Timberlake - Self - Musician
- Michael Jordan - Self (archive footage)
- David Falk - Self - Jordan's Agent / Iverson's Agent
- LL Cool J - Self - Musician
- Robert L. Johnson - Self - Businessman
- Jesse Jackson - Self - Civil Rights Leader
- Rodney King - Self (archive footage)
- Craig Hodges - Self - Former Player, Chicago Bulls
- Jerry Reinsdorf - Self - Owner, Chicago Bulls
- Common - Self - Musician
- George H. W. Bush - Self (archive footage)
- Byron Scott - Self - Former Player, LA Lakers
- Adam Silver - Self - NBA Commissioner
- Dave Zirin - Self - Sportswriter
- Pat Riley - Self (archive footage)
- Louis Farrakhan - Self (archive footage)
- Mahmoud Abdul-Rauf - Self (archive footage)
- Marc Lamont Hill - Self - Professor, Temple University
- Allen Iverson - Self (archive footage)
- Dikembe Mutombo - Self - Georgetown Alum & NBA Hall of Famer
- Jalen Rose - Self - Former NBA Player
- Steve Stoute - Self - Businessman
- Scoop Jackson - Self - Sportswriter
- Ramona Shelburne - Self - Sportswriter
- Tupac Shakur - Self (archive footage)
- LeBron James - Self - NBA Player
- Jay-Z - Self - Musician & Businessman
- The Notorious B.I.G. - Self (archive footage)
- Chris Bosh - Self - Former NBA Player
- Rush Limbaugh - Self (archive audio)
- Barack Obama - Self (archive footage)
- Shaquille O'Neal - Self (archive footage)
- Rembert Browne - Self - Writer
- Donald Trump - Self (archive footage)
- Dwyane Wade - Self - NBA Player
- Bobby Rush - Self (archive footage)
- George Zimmerman - Self (archive footage)
- Blake Griffin - Self (archive footage)
- Mark Cuban - Self - Owner, Dallas Mavericks
- Carmelo Anthony - Self (archive footage)
- Chris Paul - Self (archive footage)
- Colin Kaepernick - Self (archive footage)
- Rich Paul - Self - LeBron's Agent
- Kevin Durant - Self - NBA Player
- Stephen Curry - Self (archive footage)
- Steve Kerr - Self - Coach, Golden State Warriors
- Laura Ingraham - Self (archive footage)
- Spencer Haywood - Self - NBA Hall of Famer
- Alex Stapleton
- Vinnie Malhotra
- Chris Uettwiller
- Rich Paul
- Meghan Cirillo
- Martin Desmond Roe
- LeBron James
- Peter Mullen
- Tracy McKnight
- Nick Michaud
- Michael Huang
- Phil DeTolve
- Marc Anthony Thompson
Common interpreta a Self - Musician en la serie.
Jim Brown interpreta a Self (archive footage) en la serie.
Stephen Jackson interpreta a Self - Former NBA Player en la serie.
Charles Barkley interpreta a Self - NBA Hall of Famer en la serie.
Larry Wilmore interpreta a Self - Entertainer en la serie.
Bob Costas interpreta a Self - Sportscaster en la serie.
Jackie MacMullan interpreta a Self - Sportswriter en la serie.
Todd Boyd hace el papel de Self - Professor, USC.
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