- 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.
Cry: Come on! After all this shit we've been through, you're gonna fucking just DIE?!
- When Cry sees the prompt to handcuff Lee to the radiator so he can't attack Clementine.
Cry: Clem, you got to go. Clem you got to go!...Please. Please go... (breaks down)
- 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.
- Becomes even worse during the credits where he's outright sobbing at this point.
- His reaction the True End of The Witch's House, especially when he cheers when 'Viola' stabs the Witch and calls her a Badass and laughs at the Witch, only for his narration to get slower and more drawn out as the truth is realized. He can barely bring himself to say the line "You gave it to me in the first place. Why should I have to give it back? Right, Viola?". He only manages to narrate everything following that line in a half-dead tone.
- In the second to last episode of Richard & Alice, we finally learns what happens to Alice's son. To sum up, after an undefined period of struggling to survive in the cold, Alice starts believing that her son, Barney, has pneumonia. She keeps trying to find medicine to help him, but is only able to find insulin. Finally, after visiting the grave of her husband Mark, she goes back to Barney and shoots him as a Mercy Kill. Cry figures out what's about to happen, and his reaction is painful to listen to.
- This doubles as a Crowning Moment of Heartwarming in Cry Plays: Vampire: The Masquerade – Bloodlines 's description, considering a lot of fans think Cry would be a great father giving his caring and protective nature to Clem, Ellie and Elizabeth.
" 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.I just fear fucking up. I fear that when the time does come, I'll choke and I'll shy away from them. I don't want to do that. I don't want to be that parent who is too passive to even spend a moment with their child. I want to do it right. No matter how much I'd have to sacrifice. "
- You hear him start to get choked up at the ending of Brothers: A Tale of Two Sons
- 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.
- A few parts of the "Limelight" music video can be quite tear-jerking.
It was too soon... Way too soon... You were more of a cure than you knew... Goddammit, I loved you!
- The final episode of The Walking Dead: Season Two Episode 5, right after he's forced to kill Kenny to save Jane. His sobbing in the background is heartbreaking.
- And before that his screams and sobbing when Clementine was shot. He might have honestly believed she was dying - and that flashback with Lee...it was all just one big Tear Jerker for Cry.
- Cry's playthrough of Papo & Yo was a huge tearjerker, considering how personally it hit Cry since he admits that his father left when he was very young. It's very noticeable when he starts to project his feelings for his father on the Monster/ protagonist's abusive father as his attitude very abruptly changes from liking the strange orange Monster to being quite passive-aggressive towards Monster once he realises Monster is a metaphor for an abusive parent. The ending especially was one to break tissues out over as Cry is forced to throw copies of a girl/sort-of friend? to the monster with the implications of rape in order to progress which Cry does not react well to.
- When he reaches the end of Valiant Hearts, just all of it. His dawning realization that Emile is walking toward his execution is heartbreaking.
- His reaction to Kate Marsh's suicide in Life Is Strange. The way his voice briefly, but noticeably, cracks, and the extended period of silence he gives afterwards seal it.
- FUCK NO! GOD DAMN IT! ...Fuck... Fuck!
- His angry My God, What Have I Done? moment in his final Until Dawn video when he accidentally gets Jess and Matt killed.
- Fuck! FUCK! Great! Just got two people killed! Good job me! I run with a person I know can't run very well right now, and then I can't fucking sit still! God damn it.
- Even worse is his reaction when he accidentally gets Sam killed during the last DON'T MOVE segment.
NO! No! (Sam gets impaled with Wendigo arm) NO! FUCK! FUCK! Fuck... Fuck. God fucking damn it...
- You can literally hear the frustration in his voice, which is understanble, because up until Jess and Matt's deaths, he had managed to keep all eight alive, and there was only a half hour left of the game.
- On a less "sudden punch" note, he also gets to sound very brought-down during Josh's final segment.
Mike: All right. Let's go, you fucked-up sonovabitch.(pause)Cry: (quietly) That was rude...
- His battle with Asgore in Undertale, he's immediately starts trying everything he can to avoid him into a surrender. However, this boss won't let him. After losing twice Cry's resorted to fighting him, cutting out his audio and cranking up the game's for the rest of the fight.
Cry: "C'mon, nothing? I can't- I'm not fighting you!"
- When he makes it through the goodbyes in the True Pacifist ending and meets Asriel back where the game started, Cry gets very choked up when he runs out of dialogue and is incredibly reluctant to leave Asriel all alone in the Ruins.
- There's a moment in this playthrough where Cry thinks that Undyne has killed Monster Kid. A viewer who hasn't played/seen this game through might feel the same quiet, horrified shock as Cry in those twenty seconds. Cry's relief at seeing him alive counts as a Heartwarming Moment.
- In Episode 6 of Telltale's Game of Thrones, he is obviously very torn on feeding Cotter Nightshade to put him out of his misery or remove his heart for a ritual and he takes quite a long time trying to decide which one to do. He picks the Nightshade.
Tear Jerker / Chaotic Monki
There are quite a few moments where Cry lives up to his nickname, so to speak.