Doug, a frustrated playwright and middle school theater teacher, learns his ex is dating his nemesis, the school principal. To get revenge and cost him a Blue Ribbon Award, Doug secretly stages the most inappropriate play imaginable.
| Actor | Role |
|---|---|
 Rob LowePrincipal Brady | Principal Brady |
 Will BrillDoug Leibowitz | Doug Leibowitz |
 Gillian JacobsAbigail Morris | Abigail Morris |
 Nevada JoseMikey Gomez | Mikey Gomez |
 Melanie HerreraLata Ramos | Lata Ramos |
 Michael StrassnerCarson | Carson |
 Aidyn James AhnAbel | Abel |
 Chyler Emery SternCindy | Cindy |
 Cayden RomeroBrian | Brian |
 Lili AliceLili | Lili |
| TTanner MilburnTanner | Tanner |
 Karen MaruyamaMs. Belkin | Ms. Belkin |
 Clancy BrownErnst Rothman (voice) | Ernst Rothman (voice) |
 Dulcé SloanJanice | Janice |
 Julia AksJen | Jen |
 Clayton FarrisGus | Gus |
 Kor WrenCaleb | Caleb |
| CChris ChandlerToluca Times Reporter (voice) | Toluca Times Reporter (voice) |
 Art BonillaAngry Parent | Angry Parent |
| KKade DavisBackground Troupe | Background Troupe |
| IIsabella GuzmanBackground Troupe | Background Troupe |
| DDylan OrdonezBackground Troupe | Background Troupe |
 Jayden RobertsonBackground Troupe | Background Troupe |
| PPolina AntoniaBackground Troupe | Background Troupe |
| DDevin VillarealBackground Troupe | Background Troupe |
| MMahyar MandegarPlaywright Fellowship Awardee | Playwright Fellowship Awardee |