Please don't list this on a work's page as a trope. Examples can go on the work's YMMV tab.
Tear Jerker: Psychonauts
This is somebody's earliest memory, by the way.
Psychonauts is a generally lighthearted game (and even when it's being dark, it's funny), so this troper didn't expect to cry at it. And yet, one simple statement from the ending still gets her choked up: "Is that really what I look like in your mind?"
The final level as a whole has a really sad undertone to it if you manage to look past the Nightmare Fuel and notorious Difficulty Spike. We are, after all, looking into the mind of a boy who wrongfully believes his father wants him to die.
The asylum mates are actually a lot more depressing then their funny-crazy front you see. Gloria's mother committed suicide after Gloria told her she was mad at her for dumping her at that evil school. Fred was so extremely crushed by his defeats at the hands (Okay, mouth) of Crispin that his mind went against itself. Edgar was so utterly depressed by the loss of his girl, and coupled with the bullying from his old friends, it drove him mad (though it did give him a knack for painting), and Boyd, one of the best, silliest characters with the funnest mind-level becomes amazingly sad when you realize this is how he sees the world: Every last thing is against him. The hints about his guilt about setting his workplace on fire. The mother problems. Jesus, Psychonauts. Just... Wow.
Edgar's story becomes all the more sad when a memory vault showing him blissfully lovestruck and going on a date with said girl is accessible - after you clear his mind and therefore already know how the rest of the story goes.
Probably the most jarring example, and in turn, most effective, has to be that room in Milla's mind with that vault and that box...
"WHYYY DID YOU LET US DIE!?"
Made even worse if you later use the Clairvoyance ability on Milla. She sees Raz as a little baby, showing that she's still not too far from her roots as an orphanage caretaker.
The cut soundfiles are even worse, with Milla begging the children to stop crying before breaking down because she's telepathically hearing them burn to death. It's the intersection of Tearjerker and Nightmare Fuel.
Both of Sasha's memory vaults. Bonus points for being the first real ones we see in the game, setting the mood for what's to come.
In vault number one, we don't just get the pleasure of seeing Sasha's mother die, oh no, we see several frames of her lovingly caring for him, before suddenly cutting to his father grieving over her deathbed and then burying her in his backyard. And this is all seen from Sasha's perspective who, at the time, was an infant.
The second one is more of a Fridge Horror example, since its easy for a first-time viewer to mistake it for a comedic moment, but the implications of it are just devastating: Once Sasha grows older, he starts questioning his father about what his mother had been like before she died. He remains tight-lipped about it, so Sasha decides to use his psychic powers to probe around his memories. What he finds is a series of happy memories... and the page image for Dirty Mind-Reading. Traumatized, he runs away from home, with the implication that he never came back.
Ford Cruller, full stop. He puts on a brave face, though.
Using Clairvoyance on Ford shows that he sees Raz as a professional Psychonaut, who looks almost exactly like Sasha Nein.
Raz and Lili's sad and momentary goodbye in the final cutscene. Lili's face going from happy to sad, and watching her run away holding back tears when Raz kisses her chokes me up every single time.