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Stiffy Makane: The Undiscovered Country is a parody of AIF in general, especially the sort epitomised by the original SM, which had the MS3TK treatment. It also parodies the genre of XTrek (erotic Star Trek fan-fiction). The AIF plot structure and the Star Trek setting form the loose structure upon which to hang the jokes. And jokes there are aplenty!
This game made me laugh out loud several times and also exposed me to a surprising amount of cybertextual ergodic literary theory. I didn't expect to learn anything from this game, but I did. The funny parts for me were the sendups of people adjacent to the interactive fiction sphere at the time. The Trek/Star Wars jokes are very tired by now, 20 years on, though they probably weren't that great then either, though there was one standout moment with (Spoiler - click to show)the force ghost of a Space Moose and his timely advice.
There's a good bit of genre subversion going on, with the normal AIF skeevy dynamic of the protagonist-as-subject/NPC-as-winnable-object eventually inverted.
As well as being amused and intrigued, I was also disgusted at several junctures. It's an emotional kessel run. With music! And graphics! And very silly sound effects! Actually the multimedia elements really did add to my enjoyment here (except in one very specific instance— if you've played to the end, you know the one).
The puzzles were fair and made to be more amusing than difficult, with a particularly funny sequence where you almost have the right thing in a fetch-quest several times. I completed the game readily without any walkthrough or hints (I don't think either exist).
(Note: it deserves every one of its multiple screens of content warnings. Some parts of it really are gross.)