There were a few in Drawn to Life, which was, actually, a pretty cute game. First was a rather badly-executed death scene in the form of Wilfre killing the Mayor. It wasn't really that cute then. Second being the ending scene, which almost qualified for a Bittersweet Ending when Jowee left Mari to sail the world like he had always dreamed. A truly touching song played over this while Mari walked around the village, remembering everything they had been through before he left. Of course, he comes back. And to top it all off, your character and the ghost of Mari's father are watching in the distance when Jowee comes back. If entire scene didn't jerk any emotion out of you, that last little detail should.
The sequel, at least the DS version, is arguably even worse. It is almost impossible to explain how mind-blowingly depressing the ending is if you realize just what it entails. It's not as well pulled off as the ending in the first game, but DANG. You basically find out that the WHOLE time, everything, the entire world of Raposa has just been a dream of the kid Mike, in the real world, in a LIFE-THREATENING COMA. When he finally wakes up because of your efforts, all of the Raposa vanish. Every. Single. One. While Mike, the in-universe one, is watching, and asking why it is all happening in a panic. Now this in of itself is somewhat heart-rending. But THEN you get into actually interpreting what EVERYTHING that happened in the series actually MEANT. All of Wilfre's schemes, in all 3 games? Yeah. They were meant to perpetuate the existence of the dream world...BY KILLING MIKE. THE REAL ONE. The spreading darkness in the first game? Symbolic of Death. Don't know about the second game, but it definitely had something to do with Death. And now this game, the loss of color in the world is symbolic of, what else, DEATH. Holy fucking shit. NOT ONLY THAT, but in the scene in the end credits, you see that MIKE'S PARENTS DIED IN THE CAR CRASH THAT SENT HIM INTO A COMA. Jesus Christ. Damn you, 5th Cell. DAMN YOU!!!!!
It's not quite as bad is it seems. The Raposa's death could only be irreversible if you subscribe to the theory that dreams disappear forever when you wake from them. In real life, this is blatantly untrue, and nothing in the game contradicts that. The disappearances are indicative of Mike's awakening, but there's nothing stopping him (or Heather, depending on the interpretation of the ending) from dreaming up the Raposa again.
Even better there is the theory, that every piece of fiction is reality in another universe, and to go further, in dreams perhaps we visit these other worlds, so their world might still exist in another dimension it's just that the connection between it and the real world is severed because Mike woke up
How about how the game was designed? You start by answering three questions and sketching a picture (introducing you to the drawing mechanic of the game), but you have little idea what the significance is, and Heather makes an appearance speaking in gibberish. It turns out that this was a Book End. The questions were asked by a police officer, interviewing Heather of the events leading to the crash, your sketch is Heather's sketch of what happened, and Heather's gibberish finally comes through to Mike as he wakes up - it's a prayer for Mike to wake from his coma. Just... damn if that's not a heart-wrenching design.
I was going to buy this game until I found out about the ending. The fact that I know the ending doesn't bother me. The fact that the whole game was just a dream doesn't bother me. But the fact that Mike's parents died in the accident, his sister was seriously injured, and he himself was put in a coma and was slipping away put me over the edge.
Hell 5th Cell themselves even thought the ending to the sequel was too depressing, and actually went as far to change the ending to The Next Chapter in the Compilation Re-releaseinto something much gentler than the ending described above. YMMV whether the ending is better being changed to something a lot more happier or if it is worse because it lacks the emotional powerful sadness of 5th Cell's original ending to the game, since the changed ending leaves unanswered questions, and takes too much of the game's plot out of its original Context for example, there was never a car crash. Instead Mike falls from a tree trying to catch fireflies so Heather's face is shown as just fine and uninjured. The art in the changed ending also looks similar to the Scribblenaut's official game artwork.
Mayor Rose of Watersong being willing to sacrifice her life so that her son can be the next Mayor, feeling she paid too high a price for her vanity. And since she's an opera singer, her last song is conveyed through an actual song.
Jowee's reaction to Mari's betrayal. Even moreso when he later finds out she's Not Brainwashed.