For SHOC, you should really look at ogse mod. For CoP - nothing beats Misery.

If you knew what the ending was. specifically, then you'd know what set of circumstances would make that a game to avoid. But I've got no idea what circumstances Toxic is faced with. So I don't know if that's relevant or not. Just something to be aware of.

To make it short, my best friend - actually like a brother to me and my family - has died very unexpectedly. I found his body after breaking into his flat on April 1st in the night. Wasn't a pretty sight. And on March 30th (the day my friend actually died) we learned that my father-in-law has cancer. I like the old man very much. Actually the relation to my in-laws is in some ways a lot better than to my parents. Only a few days ago we learned that the cancer is incurable and he probably only has a few months left. A year if he's lucky.
There's more, actually the shit started to happen from autumn of last year on - one thing after the other... I won't go into details here. I sometimes feel like living in a soap opera where some new catastrophe has to happen every week to keep the audience hooked. :-/

Right now I'm starting to stomach the loss of my friend and to support my wife both helping her with the grief and dealing with the condition of her father.

The initial shock seems to be gone (though I still have flashbacks from that night). Now it hurts. I'm oscillating between deep sadness and grief and a melancholic "show must go on" attitude.
I find it quite comforting to feel "understood" by the media I consume, be it music, film or games. That's why I asked for games that could kind of reflect my mood.

That's also the reason I won't touch utter depressive games (like The Cat Lady or This War of Mine) right now, although I love them too. They might be too much for me right now and might actually succeed to bring me further down.

Again, thanks for all the suggestions so far - a lot of great ones. I wish I had more time to play right now and check most of them out. A select few I've already installed.

I am sorry for your loss. Especially given that you found out first hand like that. That's horrible to deal with. It does seem to happen like that though; you get hit by something horrible and while you're still reeling from that something else kicks you while you're down. Trying to do more than getting through each day as it comes can be very taxing at times like that.

In your case, I'd say Dear Ester would be a good choice. Like I said, it's only very particular circumstances which might make you regret playing it and from that, I'd say it's a good choice.

Gemini Rue is very good at being melancholy and is about self discovery and, in a way, loss. Vampire Bloodlines epitomises what you're talking about "something ends, something begins". You're starting over and trying to find a way of making your new life work in a pretty depressing and unforgiving world.

Dying Light is outstanding. Truly outstanding. One of the best first person games there is and it might well be up your alley. Not massively depressing, but you're up against it and trying to make your new circumstances work against all odds. But there are bits near the start that might be a bit close to home.

While it's not even close to the kind of mood you're looking for, I'll recommend the Tropico games (ideally 4) for those times when you want something that is genuinely uplifting. That game is like a happy pill for me. Probably just the setting, music and relaxing pace of play. Whatever it is, it works. Maybe not right now. But it's there.

Thanks for the suggestions. Will think about Dear Esther. I have Gemini Rue already and liked the Blackwell games a lot, so I'll give it a try when I have the time.

Vampire Bloodlines is actually one of my favourite games already ;-)

Dying Light - well I'd really like to have and play it - but it's blacklisted in Germany and GOG (or anyone else) won't sell it to me :-( A shame really, since it looks really great and would definitely be right down my alley. Fucking censorship.

Tropico - I've played the first and it's entertaining, but frankly I seem to suck at this type of games.

I would recommend Silent Hill 2, 3 and 4.

I could try to buy it through a proxy... Downloading is not a problem, since only the store pages and checkout are region locked. Usually I'd get some friend here to buy me a gift code and buy them something in return (gifting is not restricted either - got Wolfenstein this way).

Grim Dawn is on my wishlist, but since I have a very expensive house-moving ahead of me it's currently "out of range". Even more true for Dying Light which MaGog tells me is $60.

I've actually installed the original Wasteland lately, but haven't come around to playing it yet. I think I've played it on Amiga decades ago...

If you still want music suggestions, I`ll suggest Radiohead, they have depressive music, or some songs of The Cure.

:) ..have you played Primordia? It's focused around an abstract tragedy, or a distant one, more than a purely personal story, I suppose. Which is probably thankful, and avoids the suffocating and drawn out depression you often get in sad stories in dystopias of various sorts. At least I appreciated that a lot when I played it, in a similar mood as yours now by the look of things. Should be worth a look.

You don't like my recommended game? Try this list.

Currently listening to

Precious - Depeche Mode

The Wind That Shook the Barley - Dead Can Dance

Dead Already - Thomas Newman

We're In This Together - NIN

Everybody Hurts - REM

Strange Hours - Recoil

Some more recommendations (GOG)

 ▪   Gabriel Knight 2: The Beast Within
 ▪   Penumbra
 ▪   Alan Wake
 ▪   Gone Home


Links that might interest you

 ▪   Top Ten Saddest Video Games
    ( 111 games )
 ▪   6 Games That Address Grief, Loss, and Depression
    ( 6 games )

Quite a few good games have been recommended already.
Another game that I think fits here is "Home is Where One Starts...". Unfortunately it is not on GOG.
Then there is "A Bird Story". It is a pretty short game and it is more of an interactive movie than a game, but I liked it. It also has a nice and melancholic soundtrack.

Thanks! I'm not in the mood for horror right now, so I'm avoiding Penumbra though.
Thanks for the list links!

A Bird Story looks nice and it's also low-price. Might pick it up, since I already have To The Moon (installed recently, didn't come around to play it though).