
The basic story is about a lonely man (known only as the Man In The Chair) whose only source of pleasure is an old recording of a play from 1928 entitled The Drowsy Chaperone. It appears that he has a kind of love/hate relationship with it; before it begins, he talks about how wonderful it is, but as the show progresses, he pauses the record to comment on the silliness of the scene/dialogue/musical number.

As the show goes on, the Man In Chair tries to explain why certain things happen, such as the Chaperone's song about alcoholism; the "actress" who played the Chaperone (he gives backstories on most of the fictional actors and actresses who played the parts)

For the audience, the simplistic plot (the Man In Chair remarks that the entire show is summed up in one sentence at the beginning of the play-within-the-play), outrageous characters, implausible twists, and awesomely bad ending (wherein nearly everyone in the show gets married) add up to an incredibly funny experience. I am realizing while writing this that there isn't much beyond the surface to analyze, but I think that is the point. The show satirizes meaningless, awesomely bad entertainment. If a modern audience were to go see the show-within-a-show that was being played seriously, they would most likely hate it (then again, there is a shit-ton of mindless crap today that people eat up), but the product we have show that not only can mindless entertainment be fun (as long as you know what you're in for), it can also be smart (I love oxymorons).

Part of the reason the play works so well is because of the way the story is told. The Man In Chair's apartment becomes the stage of the play, and he attempts to interact with the actors, even though, from their point of view, he doesn't exist. When he pauses the record, the actors freeze. When something in the "real world" disrupts the show (like a ringing telephone), it drowns out the show. And when the incorrect record is played when the second act begins, all kinds of hilarity ensues.
I didn't realize until I started writing this that this is more of a recommendation than an examination, but this is definitely something worth seeing. Fans of musical theater will love it for the same reasons non-fans will; it makes fun of (but also praises) the genre in very accurate and fun ways.
Up next: Neil Gaiman's first appearance in The Other Worlds...
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