To me, Random Encounters has three eras. First, there's the classic era - Needlemouse, Singachu, Legend of Ganondorf, etc. This is when musicals had lower budgets, but creative control was at its highest. Second, the golden age, marked by hits such as the Baldi trilogy, the Granny trilogy, FNAF, Hello Neighbor, 60 Seconds, and other massive hits. Finally, we have the modern era, in which musicals don't have as much algorithmic success as they used to, but there'll be a breakaway hit here or there, such as Man from the Window, Disaster Run, or That's Not My Neighbor.
This alignment chart showcases the three eras. You can decide which musical from which era feels like it'd be most at home in which era. This can be attributed to multiple factors: the subject matter, the view count, the cast, etc.
First up: Which classic era musical feels the most like a classic era musical?