This article is a guide to adventure game developers on what they should avoid when making puzzles, and I stumpled upon it in my search for the most ridiciolous puzzle ever created in a game.
http://www.adventureclassicgaming.com/index.php/site/features/451/
I quite seldom play adventure games, but I know the experience of being stuck becuase of a puzzle, what interests me though, is those legendary puzzles that every one who has played certain games, has experienced. My favorit is from a game I can't remeber the name of. At some moment in the game you have to flush a toilet 3 times to open a door. To hear about this, makes life worth living, but to experience it just makes you want to die.

Now, go on and tell about the puzzles you really hate.

The mallet puzzle in Toonstruck (timing the mallet hits within mere fractions of a second to get all outcomes on that puzzle sucks big-time.

This one puzzle in Museum Madness on the ecosystems level(it's like a giant 30+ piece slider puzzle) with the food web having to be reconstructed.....that one puzzle kept me from finishing that game for a few months the first time I played it as I gave up after hours of frustration and rarely came back to it.

They didn't call it Sierra Logic for nothing.

All I need to say is: Yeti Pie.

For myself, I'd put the sleeping pilot puzzle sequence of Syberia 2 on the pedestal. It's not hard, but it's retarded on so many levels.

Another contestant: the lifeboat sequence in Leisure Suit Larry 2. That's a perfect example of Sierra at its worst (to survive a shipwreck, pick up can of spinach on the ship and throw it away on the lifeboat; if you haven't picked it up in the first place, you die of starvation, if you don't throw it away, you eat it and die of food poisoning). Close second: the stone door in the Crete labyrinth in Indiana Jones and the Fate of Atlantis when taking the Fists path. Mostly because such stuff ("push door" several times, without any indication it's doing anything at all) was so unexpected in a LucasArts game.

And a personal message to everyone who mentions the Gabriel Knight 3 moustache puzzle in this thread: I don't like you.

The "cat-moustache" puzzle from Gabriel Knight 3. I refused to keep playing the game as soon as I found out the ridiculous solution. The gist of the puzzle was to disguise yourself to look like the detective pictured on a (stolen) ID badge so you can get into a secure place. Sounds simple enough. Indeed you can collect most of the items (hat, raincoat, etc.) simply enough. But the "kicker" is that you need to make a moustache out of "something" and then somehow glue it to your face. The steps you go through to retrieve some hair from a cat to make the moustache is only part of the insanity. The worst part... the picture on the ID badge doesn't have a moustache... SO YOU HAVE TO DRAW ONE ON WITH A MAGIC MARKER!

Yeah, that makes sense! But why stop there, Sierra? How about lopping off one of your arms and then also erasing the extra appendage from the photo! Despite the fact that I played almost every Sierra adventure ever made, every one of them had some kind of a "screw the player" puzzle that was (surely?) in there for the sole purpose of selling the hintbook, which they coincidentally also sold. Remember the "invisible marker" you could rub on the page to reveal only the solutions you really needed?

You can actually read all about this particular puzzle at one of my favorite (now defunct) websites, "Old Man Murray", in this article title "Who Killed Adventure Games" http://www.oldmanmurray.com/features/77.html. The answer is pretty ironic!

I can think of 2 from kings quest 5 from the top of my head. Finding the caravan site in the desert without dying a million times and having to draw a map. Figuring out how to kill the final boss without dying another million times.

The spotlight section/puzzle area in Sanity: Aiken's Artifact(Slaughterhouse) is also hella hard, and even worse is the whole speedrun with maybe 1 second or less to spare/mess up in the beginning jail area.

50% of the puzzles in the Atlantis series drove me nuts
i must say the syberia series too had some unwanted pixel hunting and bad puzzles

My pick would be the sofa puzzle from Phantasmagoria 2. You must find your wallet and you see it under your tiny sofa but you can't just take it for some reason so you must send your pet rat under the sofa but now both the rat and wallet it stuck there and you must lure the rat out with a candy-bar and it magically delivers the wallet to you. When I played the game back in 97 it was one of those WTF moments.

I just keep thinking of horrible Sierra puzzles! There's another Leisure Suit Larry puzzle, and this is pretty vague as my memory is foggy, where I think you start on the mainland, and then get on a plane, and then jump out with a parachute and land on an island... and NOW you need some "thing" from a trashcan waaaaaay back at the start of the game from your apartment. If you don't have it now that you've played 90% of the game... and of course, there's no indication you would ever need it... you're totally screwed because of course Sierra provided no way for you to go back to your apartment now, or indeed, find a substitute "thing" on the island where you are. So.. have fun replaying the ENTIRE GAME just to get that one "thing"!

Yeah, I noticed. I maintain that if OMM hadn't written that piece, the puzzle would be all forgotten today. It isn't such a bad puzzle, really, and absolutely no reason to condemn the rest of the game; while it is arguably the worst part of the GK series, it's still pretty damn good. The cat hair thing is silly of course, but the moustache part actually does make sense. It's known that striking fake features make really good disguises; the moped rental guy would presumably focus just on the moustache and not on the rest of Gabe's face -- after all, he and Mosely really look nothing alike. I don't remember that one. I'd guess the sixth game, but I consulted a walkthrough a lot for the Larry games, just so I'd skip ridiculousness like this.

ALL Sierra adventure games. They fucking suck. Hate me if you want but i HATE these games.

That and Hand of Fate. I bought that game back in the days before internets... And it was FUCKING IMPOSSIBLE to get anywhere - I never could get past that fucking rat.... Rat tears indeed.

I still loved the graphics so I kept trying and trying. For over ten years. Until one day I decided to try and look up a walkthrough, found out how to get past the stupid rat - and it was SO absurdly illogical I simply threw my hands up and gave up on the game. Sad.

No legitimate puzzle can compare with the pain of the adventure games of the past which became impossible to finish if you missed a particular item, gave it to the wrong person, combined it with another item too soon or any number of other possibilities (some of which seemed like deliberate malice)--there was often no indication that that particular thing was the key to progressing, so you'd just keep trying everything in vain. Fun times.

some of the fist fights in the Indiana Jones and the last crusade were damn annoying and not to mention that awful 3 puzzles at the end :X :X but it was a good challenge, play that game for a good adventure challenge