No soulslike atm. I'm trying to finish my first Rimworld run. Gonna start charging my power core.

Hopefully some more Sekiro, but I've been really unwell and not doing much of anything so I'll have to see what I have the energy for. John Japansouls will be there whenever I am ready

Saddest boss fights... several people have mentioned great picks already (Solaire and Blaidd in particular), so I'll go with a different one: the fight against Leda and co in Shadow of the Erdtree. Everyone there is suddenly clear-eyed for the first time in ages, and they've found themselves as former friends now irreconcilably at odds. Thiollier and Moore trying to kill each other, Ansbach and Freya trying to kill each other, and the end of the adventuring party you had gotten to know

For a non-soulslike game but certainly soulslike-adjacent-enough that I think it's worth mentioning, Shadow of the Colossus has a couple that really have you feeling like you're probably not the good guy in this story. The 13th and 16th, most notably

The Four Kings. They're just chilling in bed playing footsies like the grandparents from Willy Wonka, when suddenly we show up and destroy their family for no reason.

Hmm, I don't know that anything really is sadder than Sif (and I haven't played Lies of P) but I'll say Artorias just to say something different. It's not really a sad fight in the same way as Sif is, where he is limping and whining - especially if you get the post-DLC cutscene before the fight. But Artorias is still sad in another way, to see the great hero corrupted and fallen and lost. Though even more than his buddy Sif it's a fight that is made all the more tragic by knowledge of the lore. The corrupted hero cliché might not hit for everyone perhaps but I guess there just aren't all that many sad fights in Souls. I feel like there is someone else that I'm missing but it's slipping my mind.

Actually as I was typing below it hit me (and I can't believe it slipped my mind): I know it's not technically a boss fight, but killing Solaire is absolutely fucking gutwrenchingly depressing. He's with you the whole journey, he is the sole source of positivity and optimism - even friendliness ("jolly cooperation!"). Then you slowly watch his spirit and vibrancy fade as he slips into going hollow, losing sight of his sun deep underground until he's mislead by a fucking oversized firefly and turned into a twisted and wrenched satirical caricature you have no choice but to put out of his misery.

"...My Sun, it's setting..."

"...it's dark, so dark..."

Yeah, fuck you Miyazaki.

Well, no Souls right now for me. Actually, I really haven't been gaming much at all the past two months. I played another two chapters of The Drifter (it's incredibly good) and another mission of Wanted: Dead (it's wack).

I'll probably play Hell Is Us soonish though, so maybe I'll get into an actual Soulslike again soon and not continue to bring disrepute and disgrace over this community by constantly writing about off-genre games.

Dinoblade has been fantastic so far. I hope I get some time to play it.

For saddest boss, I am not as experienced as most people here but I woukd probably pick The One Reborn. It's just pathetic once you take out the maidens.

No soulslike right now, because I’m working my way through the Resident Evil series in order, but this made me want to play Lies of P again.

The first one that came to mind is Sif in Dark Souls, specifically if you do the DLC first and she recognizes you. She goes from a regular monster boss to a sentient creature with a long memory and complex emotions.

Also, poor loyal puppy baby.

Oooofff. Both your picks are very emotionally charged... Lies of P definitely has some strong tearjerker moments. Romeo, and both the final boss fighths (base game and DLC) in a way, due to the emotional buildup to them...

Not a boss fight but fighting Blaidd in ER diffinitely was a gut punch as well.

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Been very out of it when it comes to games, awfully slow and unfocused but will try to resume khazan. Paused it at the Rangkus fight, very entertaining having to manage his stance break recovery... I really like humanoid fights like that one. and probably my favourite area of the game so far.

You aren't fighting that many sad Bosses… A number of sad things happen to characters, especially to the Onion boys and Alex, and a lot of sad things happen before the start of the game…

I must admit I didn't find the Sif fight sad in my first DS1 playthrough. Oh, a dog [swings Zweihander a couple of times] Oh, a dead dog and a ring. I didn't see the limping or the know the related lore. In retrospect, if you know the Artorius lore, have played the DLC, and maybe even seen the special cutscene where Sif recognizes you from the Abyss in the DLC; yes, it's really sad.

Romeo is also very sad in retrospect and makes me realize that I definitely need to replay Lies of P at some point. In NG+, I could hear the messages from the puppets, but I really want to start from a fresh save file with the promo weapon. Well, the solution is to play it twice more ;)

A third one that comes to mind is Orphan of Kos. Sure, on your first playthrough, you were more focused on the placenta that crushes your skull to paste and maybe the YYYAAOOOOWGGHH. In retrospect, you are fighting the ghost/manifestation/dream(?) of an unborn child, which is pretty damn sad.
(Also, as an aside, I just realize that the game never actually genders the Orphan. Wikis, books, etc., always assume that Orphan is male, but it's never stated in the game.)

On the whole, sad Bosses in Souls games are mostly sad in retrospect/on repeat playthroughs. Also, I feel like I missed some really obvious Bosses.

I'm going to start a new playthrough tomorrow. Probably of DS3. The SL1 routes for DS2 and DS3 sound really interesting. The problem is just ~~that I suck at DS2 and DS3~~ that I just don't know DS2 and DS3 nearly as well as Elden Ring, and I'm going to replay DS3 with a high Vigor and refamiliarize myself, and I'm probably going to press ╳ a bunch expecting to jump.

Playing Sekiro Resurrection mod currently; and I just murdered Katoro so that I could harvest the fleshy red lump out of his body after I tricked him into going to the abandoned dungeon to be experimented on by a sociopathic surgeon. Also, he cried for his daddy when I killed him, so yeah.