Early King's/Space Quest games were ridiculous , one pixel off the path and you got eaten by a giant plant or fell of a cliff. Many sudden death moments in those, which I don't really like any of the Sierra "classics". I prefer Lucasfilm's take on adventures where you can ponder on problems at your leisure.

Some of those are even better if you're on a monochrome display 😀

Yes while not always the hardest as such, the Sierra games certainly came with their share of little frustrations, and could be downright devious at times!

I can't think of any really hard adventure games I played on MS-DOS.
I can't think of anything at all notable that I played in early Windows (which I interpret to mean pre DirectX?).

But if I can go back a bit further,
Ultima 2 (Apple II) seemed so broken it was basically impossible. Every time I tried to play it was just a hopeless race against starvation which I would always lose. Supposedly it's playable but I never managed it. But since I didn't persist with that game very long, maybe I shouldn't count it.

The hardest game back in those days that I persisted with and ultimately beat was probably Infiltrator (Apple II).
I recently bought the Nintendo version of that game hoping to relive it. Everybody gives it bad reviews but I figured I had an advantage since I actually understand the game and what you're supposed to do. It has a big problem though.
In the Apple II version, when enemy guards identify you the game has slowdown caused by the alarm sound (which is CPU intensive on Apple hardware). This is a major help in protecting yourself from them.
The Nintendo version doesn't do that, it runs full speed. The guards will suddenly tackle you so fast that you can't react.

Probably any Sierra game, I mostly stuck with playing LucasArts titles as you had little to no chance of ending up in a zombie game state.

Not sure why people think Lucasarts games didn't have dead-ends, it was entirely possible to kill all three kids (separately, not by blowing up the mansion) in Maniac Mansion. Losing just one was enough to make it unfinishable.

jmarsh wrote on 2020-10-22, 04:20:

in Maniac Mansion.

I specified after 1990 in the "beginners" thread 😀

Jorpho wrote on 2020-10-14, 14:53:

McKraken has such an impressive design; I've always thought it would be great if it had a proper remake that maybe got rid of the obnoxious mazes and replaced them with goold ol' top-down RPG dungeons.

Zak McKracken reminds of Mother 2/EarthBound (1994/5). Both games take place in America (America-like place for Earthbound), are about an alien invasion, have four protagonists, and you have to collect gemstones. Also they are rather humorous.

The biggest difference is that Zak McKracken is an adventure game, while EarthBound is an RPG.

I did play EarthBound myself; I haven't gone far into the game.

jmarsh wrote on 2020-10-22, 04:20:

Not sure why people think Lucasarts games didn't have dead-ends, it was entirely possible to kill all three kids (separately, not by blowing up the mansion) in Maniac Mansion. Losing just one was enough to make it unfinishable.

Hence why I used "little to no chance" as I know that Maniac Mansion and definitely Zak McKracken and the Alien Mindbenders had dead-end / failure states, mostly if you do something like give the exploded hamster to Weird Ed. The majority of the LucasArts titles after those though for the most part you couldn't lose per se with maybe the exception of the Indiana Jones games, but those were mostly reaction / path-related.

jmarsh wrote on 2020-10-22, 04:20:

Not sure why people think Lucasarts games didn't have dead-ends, it was entirely possible to kill all three kids (separately, not by blowing up the mansion) in Maniac Mansion. Losing just one was enough to make it unfinishable.

You don't necessarily need to have all three kids at the end of the game, though. In any case, at least if you got stuck, it was fairly obvious that you needed to go back and make sure that everyone did not die rather than do some obscure, unintuitive maneuver.

A more problematic sticking point is that I think you could move the telescope the wrong way and run out of money? And the only sign that you had done something wrong would be that you saw an angry alien? The telescope puzzle didn't make much sense to begin with.

Barely any adventure games make sense to me.

I mean, carry out a complex process, to end up with the rat, which you put in the soup, to get the cook fired, so you can get offered the job, so you can get some pay in advance, so you can then use that money to move on.... I must have been living a weird life, that such paths don't naturally occur to my thoughts!

Iirc correctly from my young teens, an element of many adventure games was spending much time moving the mouse pointer over every pixel on every screen, to figure out which elements were available for manipulation. Because you certainly couldn't cognitively map out in advance, the way nonsensical processes like the above would play out.

You'd figure each puzzle out using a variety of often rote methods, and the reward would be The Joke, The Story, The Animations, etc.

Jorpho wrote on 2020-10-22, 17:46:

jmarsh wrote on 2020-10-22, 04:20:

Not sure why people think Lucasarts games didn't have dead-ends, it was entirely possible to kill all three kids (separately, not by blowing up the mansion) in Maniac Mansion. Losing just one was enough to make it unfinishable.

You don't necessarily need to have all three kids at the end of the game, though. In any case, at least if you got stuck, it was fairly obvious that you needed to go back and make sure that everyone did not die rather than do some obscure, unintuitive maneuver.

A more problematic sticking point is that I think you could move the telescope the wrong way and run out of money? And the only sign that you had done something wrong would be that you saw an angry alien? The telescope puzzle didn't make much sense to begin with.

Just kill Dave and make sure you have Bernard in your team, that's surely the way to do it, right?

Hmm ... there are a few that stick in my memory as being difficult.

Icewind Dale 2 if you go for full completion on "HARD" settings (no HOF mode) was the most difficult of the infinity engine games for me.

Wizards and Warriors was tricky. As was ROA : Star Trail. Both of those games I never finished, despite numerous attempts.

Gentlepoke wrote on 2020-10-22, 23:14:

Just kill Dave and make sure you have Bernard in your team, that's surely the way to do it, right?

it's been too long since I played the game, but I expect there's probably a bunch of workable solutions. Good replayability there – not a lot of other adventure games like that.

Iris030380 wrote on 2020-10-23, 00:08:

Icewind Dale 2 if you go for full completion on "HARD" settings (no HOF mode) was the most difficult of the infinity engine games for me.

Wizards and Warriors was tricky. As was ROA : Star Trail. Both of those games I never finished, despite numerous attempts.

Those don't really fall into the same category as Maniac Mansion and Sierra's games, I think.

If we're going to broaden the definition, then Wizardy IV surely has to come out near the top – but that's cheating, since the developers purposefully set out to make something maddeningly inscrutable. Also, I've never played it and can't imagine I would want to.

On that note, I suddenly recall the Ultimate Solution for Blue Ice. The normal solution is difficult enough, but the game was designed with a contest in mind, and even the original designers can't remember how some of the puzzles were supposed to work. Another game I haven't played and probably won't.
http://www.the-spoiler.com/OTHER/Psygnosis/blue.ice.3/

Windows 98 game - Heart of Darkness. I want to destroy my gamepad. But it was lot of fun. DOS game - hard to say, I got mostly stuck with the stupid logic of the adventure games. Kyrandia 1 - I need to draw maps in the cave section or stupid rock matching. Kyrandia 2, fireflies on the tree. Simon the sorcerer or Gabriel Knight and famous Monkey Island.

dank0 wrote on 2020-10-23, 06:19:

Windows 98 game - Heart of Darkness. I want to destroy my gamepad. But it was lot of fun. DOS game - hard to say, I got mostly stuck with the stupid logic of the adventure games. Kyrandia 1 - I need to draw maps in the cave section or stupid rock matching. Kyrandia 2, fireflies on the tree. Simon the sorcerer or Gabriel Knight and famous Monkey Island.

Heart of Darkness's hard mode with the keyboard is definitely an experience. That start of the game and then the last part of the game, that game is definitely a challenge.

Sierra had a reason to keep making "Hint Books" those days.

Earlier games are quite hard where there are some nasty puzzles that sometimes really need the hint book.

It's like making more money not just from the game, but from these hint books too.

King's Quest II had it's fair share of frustrating moments. King's Quest III is also known for it's hardness due to the time element used in it.

Even King's Quest V had it's moments. Like waiting in the room for the wizard to appear, in his castle. Who would have thought you have to do nothing and wait at a particular place to progress the story?!

Police Quest II has a moment where you have to call the operator, an actual number used in US. Coming from Asia, I had no idea what that number is. Without hint book, (or knowing what that number is) it is impossible to progress.

Quest for Glory II is particularly hard, since you have to do certain things on certain days. And it sort of loses the focus when reaching the other part of the twin city, called Raseir.

They also had a popular caller-pays telephone hint line. Go figure.

Speaking of Sierra, did you hear about Ken Williams' new book?
https://kensbook.com/

Jorpho wrote on 2020-10-24, 02:10:

Speaking of Sierra, did you hear about Ken Williams' new book?
https://kensbook.com/

Great news!