Scott: [laughing] That looked so funny! The parachute opened just as you crashed into the ground!
Cry spotting an "anti-aircraft tank carrier" flying through the air; he begins cracking up. Ironically, he saw it right after Scott finished explaining how he got shot while in a car because the game is realistic.
The highlights from Cry and Russ playing Harvester
The whole scene where the sheriff catches his deputy during his...alone time, with Cry and Russ laughing the whole time.
Russ: Take that, you bad man!
Cry: Is this some kind of snuff film or what?!
The last part of his Ib LP has him walking around the toybox his rose. During this point, he walks past Garry twice without realizing it; with the text added showing "Garry" in large letters. And later "still Garry".
This joke returns in his LP of Remember Me after the Kid Xmas fight. Cry was looking for a large set of industrial fans so he could find a collectable, and wasn't able to find them despite them taking up an entire wall of the fighting arena. So we're treated to text saying "Fans", "Still Fans" and "Never Stopped Being Fans".
Cry: (dramatic music) Fuck it! Mirror! Examine! Strange! The back of the mirror seems loose. Could there be a secret compartment behind it? What is this on the ground?! Rag! Move! What's that? There's a knife underneath. Good! Knives have been quite useful lately. Perfect! (goes back to mirror) Now, open. I fingers are too thick. Fuck that than. Use the knife. Stab!
The first video of The Witch's House LP has several great moments, particularly "Oh. It's that kind of game," and Cry's muffled screams of panic at the teddy bear monster (followed by a soft "That was fucking AWESOME!").
Cry: Sorry that, um...happened to you, but—uhhh, I'll avenge your death! No, I won't.
Cry: *turns to a lady cowering in fear* And you good? *sees her dead husband* Oh no, what happened to you? Why you dead? What happened man? I killed your husband? I'm sorry, that was not intentional. I meant to kill the other people. Because they drew their guns on me, I was just trying to steal. Their lives didn't have to be in jeopardy for my thievery! That's not how this shit works! But no, they had to be heroes! *sees lady with a kid* Fix your child!
He kills an amusement park mascot by accident.
Cry: Stay in school! *bang* HOLY SHIT I KILLED HIM!
When Cry first finds the specialized gear clothes, he comes to the conclusion that Booker was naked the whole time.
His reaction to The Stinger. "Oh fuck you! Why would they do that?!"
Cry: So uh, [Omid] right there, you gentleman, you're worried about [Christa]. Do you know why? I think it's cause you put that thing *gestures to Omid's crotch* down there in your waistline inside of that thing *gestures to Christa's crotch* in her waistline and then you're going to make a little thing like this *gestures to Clementine*...Go Omid. Tappin' that bosom.
Cry: (in a high voice, and trying not to laugh) We are going to skullfuck your pets! Everything you know and love is forfeit! (Evil Laugh, followed by the cult breaking into a guy's house)Konnichiwa! You're dead!
DUDE WHO GAVE ME FOOD THE STREAMERS ARE OUTSIDE OF YOUR HOUSE
In Vampire the Masquerade Bloodlines, Cry's insistence on dancing at every club, especially when it results in an awkward moment reaction from the NPCs.
The part in Dishonored where Cry retrieves the whale oil for Piero and, not realizing how explosive the whale oil is, proceeds to throw it at the machine, accidentally killing Piero in the process. His sheepish laughter and apology tops the whole moment off.