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Tear Jerker: Chaotic Monki
There are quite a few moments where Cry lives up to his nickname, so to speak.
There are several scenes in To the Moon where he gets noticeably choked up, but many people think that the saddest part was the ending of Part 11 - specifically, the scene where River is removed, and the flashback that follows it. Before the the scene starts, he can't seem to do anything else but plead with the game for River to be alright. Once the scene begins, his voice is shaking so badly he can barely read the little amount of dialogue there is. Throughout the flashback, you can hear him sobbing quietly. Arguably, what's worse is that he doesn't take time to regain his composure after the scene-and the video-end. In the next part, you can tell that he's still crying a little. Cry's videos are an example of how sometimes, having commentary over a game doesn't detract from its emotional impact, and in rare occasions, can add to it.
The last ten minutes of the finale to Ib is noteworthy. It all starts when Cry is forced to give Garry's rose To Mary in return for Ib's rose. While this is happening, Cry desperately pleads for Gary to not go through with it and tries his absolute best to get Ib to communicate that to him. When Garry does go through with it, Cry gets very upset and apologizes profusely to Garry to the point of tears. It only gets worse when Mary kills Garry. Cry then becomes silent for a good while and then swears to kill Mary. Sadly, Cry is on the path to the worst ending and is forced to watch Mary get off scotch free and have Ib befriend her. This all goes down with Cry seething in anger and sadness. At the very end, Cry simply says "I'm just gonna go now and just... I'm just gonna go now." as the video fades to black. The kicker of course is that Cry left thinking that that was the only ending. Watching Cry get so engrossed in the game and then get denied a happy ending in place of the worst one while the viewer knows that there are better endings is just soul-crushing.
Cry's LP of the Amnesia custom story A Visit To Katherine. He talks to himself as he goes about discovering the recordings Katherine has left for the player-character, expressing delight in the knowledge that she's apparently the player's wife, that it's their anniversary today...and then he finds out Katherine is an Ill Girl. As he finds recordings of Katherine saying she hates for her husband to see her reduced to the state she's in, Cry says that he's sure he'd love Katherine "even if you vomited all over yourself." Then he finds out the player-character wakes with amnesia every morning, having developed this before Katherine's own illness got worse and he slowly starts to break down...And finally he finds the recording revealing that Katherine died of her illness prior to the game, and this is her last goodbye to the player. Cry finds the player-character in front of Katherine's grave and is just...speechless. When he finally does say something, all it is is a quiet, despaired "Oh no..."
In his Let's Play of The Last of Us, Cry gets very upset when it appears that Joel has died, and Ellie is left on her own, during the start of the 'Winter' chapter. At a few points (including during the cutscene leading up to said chapter) it sounds as if he's on the edge of tears, and for several minutes can only splutter in anguished disbelief.
During is The Walking Dead LP he fails to kill The Stranger. After Clementine kills The Stranger for him all he can manage is a gasp while saying her name softly.
When Cry sees the prompt to handcuff Lee to the radiator so he can't attack Clementine.
Cry:Come on! After all this shit we've been through, you're gonna fucking just DIE?!
When the ending comes along you can clearly hear him crying in the background the whole time. When it looks like Clementine might stay behind with Lee who is soon going to reanimate as a zombie he begs her to go.
Cry: Clem, you got to go. Clem you got to go!...Please. Please go... (breaks down)
Becomes even worse during the credits where he's outright sobbing at this point.
" When I have a kid, I really, really hope I keep the passion I have in me now and direct it towards raising him or her. I don't want to fail them. I want to make sure I am always there for them when they need me, but give them space to grow as they wish. I don't want to mold them into my own image, I want them to branch out and become someone truly unique, but if that fucker gets outta line you bet your ass I'll bring out the discipline axe.
The end of Bioshock Infinite: Burial at Sea Episode 2, in which Cry is very clearly left shell-shocked by the finale of not only the game, but possibly the series itself.
When Elizabeth dies at the end of Episode 2, all you hear is a watery "...no...no..." before the credits roll. Considering how attached and protective he was over her through the course of the game and his elation at playing with "Elly" again, this is a major heartbreaker.
His readings of the dialogue in the more emotional parts of The Crooked Man. They are both frightening and extremely tear-jerking.