Depending on your actions and interactions with Barry while you play as Jill, Barry can get killed, leaving behind a photo of his wife and two daughters with a note saying how he'll miss them and watch them from heaven. Doesn't help that the music that plays drives the point home.
In REmake, just clear the mansion as much as you can, wander the halls, and ponder the deaths of the other members of S.T.A.R.S. for a little while. Especially Edward (poor little teammate Rebecca), Forest (Jill's version of the scene where he's discovered dead does have impact), or Richard (especially if you fail the Timed Mission that ensues after first running into him). All a bunch of brave and perfectly likable men who had no idea what they were up against and ended up brutally murdered. They had a certain amount of backstory, character, and all of that. And you know what? Most of S.T.A.R.S. were kind of friends. And you have to turn out to be just too late to help them out. Seriously do factor in characters' histories with each other the best you can, too - fail the aforementioned Timed Mission as Chris and Rebecca has to watch the guy who showed her the ropes as a S.T.A.R.S. member die; Chris and Forest were somewhat close as well as friendly rivals, and if the latter's zombification doesn't hit you a little bit during a Chris playthrough, have a peek at this, focus on Chris at the very end and listen to the zombie's moans niiiice and closely... Oh. Also Enrico. There was a mission in Umbrella Chronicles from Rebecca's point of view in which she and Richard are searching for their captain, sure that once they find him, everything will be all right. Yeah. Not only does he die, he's last in the game's body count. Not only is it painfully clear that he wasn't able to save his men, the last thing he realizes is that it's because they were all betrayed that all of this had to happen to them. Whether or not any of this actually gets you crying depends on who you are, but it's bound to at least spark a "...son of a bitch" kind of reaction.
Might be slightly mitigated by the fact Everyone Lives in the canonical version of RE 1's storyline.
Well, everyone besides those mentioned above. But Wesker had it coming at least. In any case, the worst part is that whether or not he knows it, Enrico dies a failure as a leader, as he's the last member of the team to die, leaving Rebecca alone.
The remake/port of the first game on the Gamecube has one. If you are playing as Jill, when you meet Barry in the underground of the mansion, he points his gun at her since Wesker manipulated him by using his family as blackmail. Jill wrestles the gun out of his hand and aims it at him. The monster that has been stalking the player appears and Barry frantically begs Jill to give his gun back. If you say yes, you'll be on the road to the good ending. Say no, and you'll see Jill hesitate, which at this point, the monster attacks Barry, knocking him into the abyss as he drops a photo of his family near Jill.
It's just as bad in the original; When you go to the mansion's underground, split up with Barry (answer "no" to both of his questions; he otherwise lives), and either not before long or at the end of the game, a Hunter/Tick murders him. He can say nothing but admit his carelessness to Jill, and wishes her to give his photo back to his family. This version gives us some of the saddest BGM in the series, as you read the message written on the back of the photo: To my dearest Moira and Polly, I love you, and I hope you grow into strong, capable women. That's pretty damn sad.
For that matter, the story behind the monster, Lisa, herself, she was once a little girl whose father designed the mansion and unfortunately knew its secrets. She and her mother were kidnapped when Umbrella muredered her father. The two were experimented upon with what would become the T-virus until her mother died. Lisa wasn't as fortunate; she mutated into a grotesque form and her mental faculties degenerated. Lonely, and obsessed with her mother, Lisa went insane. It gets really depressing when you read her diary and the messages from her parents dotting the game.
Combine Lisa's diary, her mother's letter ("I wish I could touch your face and hold you in my arms right now..."), her father's diary ("Because of my ego, I got both of you involved in this whole damned conspiracy. Forgive me."), and add that pitiful moan at the end on top of it all, "Mo...ther..." Dear God...that last little touch is like twisting a knife that's already embedded in your heart.
Also, EVEN WORSE? The experiments gave her invulnerbility not unlike Wolverine (As during the battle between her and Wesker in Umbrella Chronicles, her health meter depletes but just as quickly restores) making her almost immortal. So add, And I Must Scream to the list of tragedies. Though that same battle ends with Wesker shooting the chandelier down, pinning her to the floor as the mansion explodes. more or less confirming that Lisa died (Hopefully)
Around midway through the game, you'll encounter a S.T.A.R.S member named Richard, who has been bitten by Yawn, the giant snake, and needs you to get him some "serum". In the original versions, you are always one second too late to save his life, no matter how quickly you fetch it and bring it back. In the REMake renditions? You can save his life with the serum... but, for continuity's sake, he still has to die. So he ends up being eaten by either Neptune (for Chris) or Yawn (for Jill).
If you're playing as Chris, he breaks this news to Rebecca after the battle with Plant 42, and if you follow Rebecca into the medical supply room and ask her to heal you, she breaks down crying.
Jill's version is just as bad, because he bursts into the room to save you during the semi-optional (you have to encounter him, but you don't have to stick around and fight) Yawn encounter, only dying to save you at the end of the fight. Thing is, that part about it being optional? If you try to be clever and just grab the MacGuffin and run, he still dies; you just get this horrifying cutscene where Jill leaves the room and you hear Richard's death-scream behind you...
And then, as an extra metagame-level Player Punch; normally, Richard's death results in you getting his automatic shotgun. If you trigger the above mentioned cutscene? Richard dies and you lose the auto shotgun. Permanently.