The Inkwell is about a 16-year-old boy coming of age on Martha's Vineyard in the summer of 1976.
| Actor | Role |
|---|---|
 Larenz TateDrew Tate | Drew Tate |
 Joe MortonKenny Tate | Kenny Tate |
 Suzzanne DouglasBrenda Tate | Brenda Tate |
 Glynn TurmanSpencer Phillips | Spencer Phillips |
 Vanessa Bell CallowayFrancis Phillips | Francis Phillips |
 A.J. JohnsonHeather Lee | Heather Lee |
 Morris ChestnutHarold Lee | Harold Lee |
 Jada Pinkett SmithLauren Kelly | Lauren Kelly |
 Duane MartinJr. Phillips | Jr. Phillips |
 Phyllis Yvonne StickneyDr. Wade | Dr. Wade |
 Markus RedmondDarryl | Darryl |
 Mary AliceEvelyn | Evelyn |
| RReggie McFaddenMC Madman | MC Madman |