Replying here since I have no clue how else to reply on this site. I may not be the best person to ask since most of the time what most people consider bleak and depressing-looking I just consider beautiful. The only thing that depresses me is bad games. Or games whose graphics are overly realistic or otherwise uninspired. I ran across a small and extremely unusual game recently called 0_abyssalSomewhere that's about as bleak as it's possible for a game to look and I thought it was beautiful — for its bleakness and for how inspired its look was.

Now, I have no clue what kind of bleakometer you're working with, or how many point-&-clicks are in your field of reference. If Grim Fandango's too bleak-looking for you I can't help you (course that's not a point-&-click in the most technical sense, but anyway). Of course you could be thinking of things like the Syberia games or The Longest Journey, and the environments in those aren't necessarily to my taste that much either.

Now of course the main problem is that point-&-clicks were practically extinct by '99 as far as professionally made, feature-length games by companies anyone had heard of go and they didn't crawl back out of the grave in any serious way till 2009, so there really isn't that much good stuff to choose from in the era you're asking about unless by 'late 90s' you mean the latter half of the 90s, in which there's still a lotta good-looking games. You'll just have to look up games on the second and early-part-of-the-third page on my list there — I always write notes on the games I think look good.

The only adventure games from the late '90s to early naughts I think are actually worthy of a mature human's precious time are Grim Fandango and Curse of Monkey Island and of course everyone knows those two anyway. Course there's also Peasant's Quest, I guess. I did think Runaway: A Road Adventure had a lot of attractive scenery (pretty clearly inspired by Monkey 3) even if the game can be a real chore to wade through and the writing's idiotic (also has at least two of the most insanely stupid and illogical puzzles I've seen). Not one of the better eras for adventure games.

@BrianMcInnis Wow, thanks for the detailed response. The games that made me consider the bleak style were games like Syberia, Sanitarium, Zero Critical, Harvester, for example. They all have this foggy, muted, industrial, brutal tone that makes even their more colorful/brighter scenes look very bleak to me. I haven't actually played any of those games, nor Grim Fandango, but even GF shares some of that greyed out aesthetic.

I brought this up on the Backloggd discord as well and thought about how all these games utilized 3D, especially pre-rendered 3D environments. Maybe because this was the early days of 3D game design, some of the shapes used were quite rigid and polygonal, and render distances might have been helped by adding lots of fog in some cases. Also, experimenting with 3D shadows in some of the pre-rendered stuff led to some huge contrasts in lightness/darkness which I think is pretty evocative of that depressing/creepy tone.

By the way, love your list. It's incredibly definitive from what I know and has let me trace the history of point'n'click games and discover some new stuff to hopefully get around to trying out.

@tendog Ah, that's how one (sort of) replies here. Thanks. And I'm so happy to hear my list has been useful to you.

Yeah, most of the games you mention have some fairly hokey graphics, though I am fond of a lot of those old background renders. I haven't played through any of them either, or many others like them (never had Playstations or Windows computers at that time), but I've started Syberia and I'd like to play Sanitarium some day; its environments have a certain charm that attracts me. I actually run a rather well-subscribed Twitter account called Old-School 3D Renders that's dedicated to that sort of thing (though I haven't posted anything since Christmas! Gotta get back to that). I'm working on writing a bunch of point-&-clicks of my own and some day I really want to do one that looks like promotional 3D render art from around the late '90s. Can't believe no one ever made any games in that style. Or really I guess they more or less did with games like Kyrandia 3, Kingdom o' Magic, Armed and Delirious and others, only the renders were all hugely scaled down in quality in order to fit the size limitations we had then. But then as soon as size capacities increased, digital rendering had 'advanced' out of that aesthetic altogether.

Yeah, I guess I'd say I easily prefer natural-landscape bleak to the industrial variety. That sounds like a very informed explanation for why all the fog and shadows in those games. It reminds me of what some designer from LucasArts said about the early pixel days, that because of the graphical and especially color-palette limitations they had to work with, 'night became our friend.' Hence all the night scenes in Maniac Mansion, Loom, Monkey 1 and so on.

Anyway, Grim Fandango has a certain amount of scenes that could be called grey and maybe foggy I guess (film noir is one of its central inspirations), but it definitely couldn't be called a visually bleak game. Most of it's very colorful — very often extremely colorful in fact, with all the Mexican influence — and more importantly it's got probably the most ingeniously inventive and original visual/architectural world of any adventure game (also one of the very best-scored and almost certainly the most wittily written and best voice-acted). You oughta give it a try as soon as you can. You'll almost certainly need to look up some of the puzzle solutions (some of them can be damnably technical and fidgety), but anyone'll tell ya it's one of the great adventure games yet made. In fact from what I've seen it seems to be more or less the consensus view that it's the best, though I don't place at the very top myself. Adventure gamesters seem to generally consider clever, funny dialogue to be the most valuable of all elements in a game and I don't.

Alright well I've jawed on long enough. Very nice chatting with you, tendog. Boom shanka.