Let me preface this by saying that there is a lot more to The Entertainment than I have parsed out. This is only a portion of my small corner of personal reaction and why I can't stop thinking about the game. You should try playing the game before reading this.
The Entertainment is set in the world of Kentucky Route Zero, the magical realist adventure game from Cardboard Computer. It plays off of this in several ways. The Entertainment's play is set in Kentucky, and the set was designed by Lula Chamberlain, the oft-referenced artist (the other short Cardboard Computer has released in the KRZ universe featured an artist retrospective on Lula) who the player encounters in KRZ's second act. There is thematic spillover as well as debts, work, and family are tackled in both The Entertainment and KRZ. The Hard Times Distillery and Junebug, featured prominently in KRZ's Kickstarter, also make concrete appearances.
Cardboard Computer has said that they are taking a theatrical approach to games, whereas the majority of games have taken a more filmic approach. The scenes from KRZ are heavily inspired by dramatic sets. In The Entertainment they take this approach and literalize it – you are actually viewing a play. This comes as a shock, as initially the scene looks like it will follow the interaction model the player has become so accustomed to in KRZ.
Not only has Cardboard Computer taken inspiration from theater in their sets, but also their interaction models. Here's an excerpt from an interview with Jake Elliott on Rock Paper Shotgun.
RPS: Now that you mention it, that does make a lot of sense. I felt a lot like I was putting on a performance whenever I was playing it. Almost like the bits where I could pick dialogue were improv. I could add a little bit to Conway based on what I wanted to bring to him, but my choices didn’t change the overall plot progression.
Jake Elliott: Yeah, totally. We’re thinking of it like the way that an actor chooses… They don’t necessarily choose the dialogue or the plot, but they choose how to inflect it and how to think about, depending on their method of acting, the inner life of the character. There’s a lot of construction that happens, creative construction that happens at the level of the actor in a play. We’re trying to put the player in that role.
In Kentucky Route Zero this is done entirely through dialogue. In The Entertainment the mode of character inflection is purely kinetic. The player is a silent and immobile actor in a play.
The game's page describes 'The Entertainment' as a "simultaneous performance" of 'A Reckoning' and 'A Bar-fly'. This description falls right in line with Jake's vision for the player's role as an actor-like agent. Kentucky Route Zero itself could be viewed as a play within a play – the play of the world of Kentucky Route Zero, and the play of the player's interactions with that world. The two happen in parallel, occasionally interacting and acknowledging each other.
'The Entertainment' is like Kentucky Route Zero has been passed through a filter where the variables through which we understand the world have been skewed, shifted, and in a certain instances boiled down. The world is being presented as a sort of metafiction being carried across multiple mediums – a play ('The Reckoning') within a play ('A Bar-fly') within a fictional world (the world of Kentucky Route Zero) within a game (The Entertainment). This wrapping becomes even more complex as the player is presented with both fictional reviews of the play, and directors notes, throughout the game.
There's a ton more I'm still chewing on with this game. The fact that acting has been completely removed from the situation – the characters all have blank faces and the player must add all inflection and expression to the lines of the play. How intentional the tempo of the dialogue was, making the player fight against their connection of slow dialogue to filler in games that is usually placed in a game purely as worldbuilding, and not treated with any sense of import (the bar dialogue feels like it could happen at a cantina in Mass Effect and the player would just walk past it in a heartbeat). The choice to have a jukebox list out the sound effects for the current act. What the characters' relationship to entertainment is (and the fact that the game and play share a name with the deadly Entertainment in Infinite Jest). There's just tons to digest about this game, and that's part of what makes it so great. Hopefully this will help set you on a path to finding your own corner of things you find interesting about The Entertainment.
p.s. I'd love to hear what you think on twitter.