• 
  Mike Wiley

  Henry Box Brown
• 
  Tommy Allen Taylor

  Mister Colquitt
• 
  Brandi Nicole Feemster

  Nancy
• 
  W. Scott Parker III

  Dr. Smith
• 
  Jody Vines

  Croetus
• 
  Jeff Briggs

  Sam Cottrell
• 
  Bernie Ask

  Cobbler
• 
  Lex Wilson

  James Jr. (as Alex Michael Wilson)

• 
  Carl Martin

  Master Barrett Sr.
• 
  Matthew W. Downing

  William Barrett
• 
  Timmy Richardson

  Henry as a Boy
• 
  Jennifer Evans

  Henry's Mama
• 
  James W. Burriss

  Mister Leigh
• 
  Kenneth Hinton

  Henry's Uncle
• 
  Jeremy V. Morris

  Joseph