Play it if: you want a short, sweet line of puzzles with a couple of good twists.
Don't play it if: you want a less linear, more open game that lets you take your time and explore, or a spy story that focuses less on plot and more on theme.
At least at the time of its release, Spider and Web was obviously a novel concept for IF, if not so much for storytelling in general (connections to Rashomon have already been pointed out, but let's not forget The Murder of Roger Ackroyd; and The Usual Suspects, which had hit the theaters in 1995). Me, I came to IF relatively recently barring Zork I, so the historical impact of the game is lost on me. But does it hold up by itself?
Yes. Putting aside the then experimental nature of the game, this is still an appreciably good bit of IF. One thing I've always liked about the medium is that, aside from the really early history, IF can age extremely well, and this is one work which feels like it could have been written yesterday.
Aside from a couple of people who seem not to have finished the game, there's not much other than high praise for Spider and Web here. Most of the positive aspects of the game have already been outlined. So I'll mostly skip that, except to say that I really love games like this and Sean Barrett's The Weapon, where you have to discover and solve at the same time, and do it under observation (it really adds a sense of urgency and pizzazz to the puzzle-solving process). Instead I'll take the time to address some of its flaws.
This is necessarily spoiler-heavy, so...
(Spoiler - click to show)In terms of gameplay before the big reveal, there are one or two moments which feel somewhat underclued. The lockpick distraction method doesn't entirely make sense to me, not least because the lockpick strikes me as the tool a master infiltrator would be least likely to part with. I might as well have just thrown the minilamp, surely? It didn't also make much sense to me that the functions of each dial on the timer weren't explained in the descriptions of the dials; pretty much everything that wasn't intuitive for the other tools was explained upon examination, so why not the timer?
The game does lose a lot of my interest after the big reveal, and I think it's because the climactic sequence is longer than it really needs to be. In a longer game with more varied puzzles I would have found it acceptable, but choreographing your efforts to complete the game takes up enough of the gameplay time that it feels like another game tacked on. It doesn't help that the puzzles bear little relation to what you've been doing up until that point, with the exception of the common geography.
I accept that it might have been difficult to squeeze the post-escape sequence into just a few paragraphs of exposition, and there's no honest middle ground between the two options...but then I simply have to chalk it up to the story being written into a corner, albeit an enjoyable one. The Usual Suspects, in contrast, basically ends with that analogous twist and, regardless of whether or not you appreciated the plot that came before, I think it's fairly obvious that setting the film's climax after that reveal would have been a lot less punchy and a lot more tedious.
I also have mixed feelings about the discussion of moral concepts in the story. Don't get me wrong, I'm a sucker for Cold War narratives and the murky worlds of arms escalation and espionage, but in order for such narratives to work you need the other side to give you something to work with, and while the interrogator has a good deal of personality the PC has almost none (aside from a few flashes of attitude in the first couple of turns). While the conceit of having the PC know more than the player is well-done, it would have worked even better had it been connected with the moral dimension of the story. If the PC actually responded to the interrogator with opinions and ideas, it would have added an extra layer to the intrigue: is what you're saying part of the patter to get him to accept your story, or is it actually what you believe? Or is it even both? The ambiguity in the game is purely external - by which I mean it affects the plot, not the actual stances and opinions of the player character.
In the end, this is still a very good game, and I would argue, worth your time. It's not really a masterpiece, though. A generally well-done employment of one or two neat tricks in a story short enough for them not to outstay their welcome.
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