In a 70s landscape of theatre, a charming dream-chaser says hello to the love of his life for the first time. 50 years later, a simple hill is preventing him from saying goodbye.
| Actor | Role |
|---|---|
 David MasonStanley | Stanley |
 James SpragueYoung Stanley | Young Stanley |
 Mark ArfurRobbie | Robbie |
| LLauren StokesYoung Dorothy | Young Dorothy |
 Emily AshAlice | Alice |
| CChelsea KunatsaKim | Kim |
| CCarol FletcherDorothy | Dorothy |
 Jack ManifoldDVD Workout Instructor (voice) | DVD Workout Instructor (voice) |
| CCheyenne ChristieDancer | Dancer |
| BBecky LintonDancer | Dancer |
| RRiver HoosenDancer | Dancer |
| MMegan LangDancer | Dancer |
| EElle AllenDancer | Dancer |
| KKate WhiteDancer | Dancer |
| KKaren GrahamPizzeria Goer 1 | Pizzeria Goer 1 |
| MMarie MaguirePizzeria Goer 2 | Pizzeria Goer 2 |
| SSam DudleyPizzeria Employee | Pizzeria Employee |
| BBilly BookTownsfolk | Townsfolk |
| CChristine StephensonTownsfolk | Townsfolk |
| RRay StephensonTownsfolk | Townsfolk |
| KKaren AlcockTownsfolk | Townsfolk |
| LLucy LidstoneTownsfolk | Townsfolk |
| CCharlotte ClowTownsfolk | Townsfolk |
| HHolly HoustonTownsfolk / Judge 1 | Townsfolk / Judge 1 |
| BBen MirfinJudge 2 | Judge 2 |
 Jacob PerkinsJudge 3 | Judge 3 |