wordplay games have always been a tough genre to get right. on the one hand, you want to have consistent rules for word manipulation, so the player isn't just sitting there guessing words. you want to have the puzzles actually fit together into a larger picture, whether that's a treasure hunt (Letters from Home) or a detailed plot (Counterfeit Monkey). you need to make sure the game is tuned to the language, not to pop culture references, to ensure the game doesn't become incomprehensible five years from now.
out of the short stories that make up Nord and Bert Couldn't Make Head or Tail of It ... one, perhaps two, fit any of these criteria.
the general pattern of these stories is to recognize the kind of "wordplay" at work in the story, then just examine items and type every example of that wordplay you can think of. in "Playing Jacks," you have to know a lot of words that have "jack" in them. in "Shopping Bizarre," if you see an item, you type its homophone. the biggest offender here is probably "Eat Your Words," which is just see object, type cliche naming object, continue.
there is a single highlight here: "Manor of Speaking." it's a haunted house game where each ghost has a different obsession, and you play them off against each other and solve actual puzzles riffing off wordplay. it's brief but delightful.
by contrast, the worst of the lot is "Act the Part," which requires the player to be familiar not only with unfunny gags from downmarket 1950s sitcoms, but also to recognize a phrase that is as opaque to me now as it was back then ((Spoiler - click to show)"better a bottle in front of me than a frontal lobotomy"). this stuff was dated when it came out. (ironically, the opening-move puzzle in "Act," despite being incredibly frustrating, is one of the few that's stood the test of time.)
similarly culture-specific and extremely difficult are "Buy the Farm" and "Shake a Tower." "Farm" is at least well-written (most of Nord and Bert has nothing but short, terse responses) but some of the expressions in it are already passing out of English parlance. "Tower" uses spoonerisms, but it's also very cruel, utterly nonsensical, and nearly impossible to get a perfect score on.
people talk about the Oddly Angled Rooms from Zork II being too culture-specific. at least there there are at least three countries whose inhabitants should get the joke.
if all of this were beautifully written, or tied together in a coherent fashion, it might be another story. but it's just checking off disparate scenarios until you're allowed to go on to the last one, "Meet the Mayor," which is basically the same as "Buy the Farm" but with much more obscure language. (some of the phrases in "Mayor" are so obscure that even now, almost thirty years later, i've still never heard anyone use them.)
most of the games that Nord and Bert inspired did the job better. i was a huge Infocom fad, to the point of a fault, but there are still a couple of their games that i just can't defend. this is one of them.