Classic point-and-click adventure games are notorious for making players perform absurd mental gymnastics to solve their puzzles. In these games, simple problems rarely have simple solutions. A particularly infamous example can be found in Monkey Island 2: LeChuck's Revenge, in which would-be pirate Guybrush Threepwood has to use a water pump to drain a waterfall that's blocking his way. The handle is missing, but it isn't just lying around somewhere waiting to be picked up. This is an old school LucasArts adventure game after all. The solution is much, much sillier.
Step one: head to nearby Scabb Island. Here you'll find the Bloody Lip Bar & Grill, where a monkey named Jojo is playing the piano. Above the piano is a metronome, on which you stick a banana you just happen to have stuffed in your pirate pants. Jojo is frozen by the delicious-looking fruit swinging hypnotically back and forth in front of him, letting you pick him up and shove him in your impossibly deep pockets. Step two: head back to the waterfall on Phatt Island and use Jojo's stiffened tail—which is shaped like a wrench, kinda—on the pump. Waterfall drained, puzzle solved.
Turns out all you had to do was find a monkey wrench. A lot of people, quite reasonably, did not find this amusing. LucasArts received a flood of letters from frustrated and perplexed players—and I'm sure the company made a tidy profit from desperate calls to its premium hintline too. This is a prime example of '90s adventure game puzzle design. It's ridiculous, sure. A pun that spun wildly out of control. But when you take a step back and think about the solution, it actually makes a twisted kind of sense—certainly within the loose bounds of Monkey Island's slapstick, cartoonish world.
But that's nothing. In another point-and-click adventure game—1999's Gabriel Knight 3: Blood of the Sacred, Blood of the Damned—there's a puzzle so stunningly, legendarily bad that it has its own Wikipedia page. The so-called cat hair moustache puzzle is widely regarded as one of the worst puzzles in the history of the adventure genre, with a solution so mind-bendingly illogical it defies belief. It involves impersonating a detective named Mosely so you can take his motorcycle rental for yourself. Doing so involves creating a fake moustache—even though Mosely doesn't have one.
You stick a piece of masking tape to a shed, then startle a cat with a garden hose so it runs past and leaves some fur on it. You then steal Mosely's passport and put on a baseball cap to hide the fact that, unlike Mosely, you have hair. Then you use a blob of maple syrup to stick the cat moustache to your upper lip. Finally, you use a magic marker to draw a moustache on Mosely's passport photo to reflect the makeshift facial hair that is crudely glued to your face. Et voila. The rented motorcycle is now yours. If you figured all that out without a walkthrough, you're probably lying.
Not only is the sequence of events involved in solving the puzzle far-fetched and laboured to the extreme, but the entire puzzle is based on the confusing premise that you are making a moustache to pose as a man who does not have a moustache. The fact you have to draw one on Mosely's passport to complete the disguise only serves to highlight the bewildering idiocy of the whole caper. It's staggeringly stupid, but a part of me admires the gall of designing something so unhinged. It's like the developer intentionally set out to make the worst adventure game puzzle imaginable.
People often cite Broken Sword's infamous goat puzzle—which also has its own Wikipedia page—as the premier example of annoying adventure game puzzles. But while that is a particularly egregious example, it's a beacon of sense and reason compared to Gabriel Knight's cat moustache. The goat is frustrating because it introduces a timing element that isn't part of any other puzzle in the game before or after it. The cat moustache is frustrating because it doesn't make a lick of sense and is actively hostile to the player. But love it or hate it, it's officially a part of gaming history now.