Tippy Winston's journey continues. Her plan to reform the hood and make everyone rich is constantly in jeopardy.
| Actor | Role |
|---|---|
 Towanda BraxtonTippy Winston | Tippy Winston |
 Denzell DandridgeMalik Winston | Malik Winston |
 Crystal HughesKarrine | Karrine |
 Teresa CelesteSimone | Simone |
 Alphonso A'Qen-Aten JacksonZilla | Zilla |
| JJocelyn CastorTony | Tony |
 Marquise ClarkCujo | Cujo |
 Brendan GoshaySpike | Spike |
| LLana S. ShieldsSade | Sade |
 Fred GalyeanCongressman Bell | Congressman Bell |
| BBakari BloctonYoung Malik Winston | Young Malik Winston |
| RRaniqua EnglishNicki | Nicki |
 Cheryl FrazierMs. Woods | Ms. Woods |
 Marlon C. HayesRock | Rock |