In their brief Let's Play of Amnesia: The Dark Descent, beginning at around 13:00, Josh maneuvres on top of the monster, making it impossible for the monster to hit him. This, together with Josh throwing barrels at the monsters, partly makes for a great Crowning Moment of Funny, and partly removes the feeling of fear from the monsters.
Some of the VATS animations in their New Vegas LP go beyond insane. They're truly a hilarious wonder to behold.
Every person in a room in the White Glove Society's casino is murdered by Reginald, except for one woman that is sitting down at a gambling (blackjack, maybe?) table. Reginald proceeds to casually sit down next to her and attempt to gamble, but the dealer is lying dead a room or two over.
"Your cannibal religion-"
"It's not a religion, it's a hobby"
Rutskarn's enraged outburst in the intermission episode where they play Trainz 2010: Engineer's Edition.
Rutskarn: No! No! You are building a game that is literally on rails - literally on rails! It should not be going off the map!!!
Mumbles: Into the great unknown...
Rutskarn: This isn't even alpha!
A train went through a car
The entire episode could count for one of these, in between the horrible bugs, Microsoft Sam doing narration, the non-stop snark and let's not forget the Hurricane of Puns near the end.
In episode 19 of the New Vegas series after Josh kills ranger Jackson with a sneak attack, he says as he walks out.
Josh: That guy's not a corpse back there, he's lying to you.
New Vegas, Episode 42: Josh is being lectured for causing Shamus' mental breakdown, and in the middle of it he nonchalantly says, "Ooh, there's a frag mine."
Also, Shamus' Call Back to "I get to decide who has a gun, and it's always ME!"
The Great Crash, sent from the cosmic heavens to punish Josh for nearly driving the rest insane during this episode.
Once it occurs, the cast make no reference to it or the leadup.
New Vegas, Episode 30: Christine spending two whole minutes trying (and failing) to kill Reginald Cutfbert, and completely forgetting about it two minutes later.
"I would like to assure our viewers at home that no children were harmed in our attempts to murder the children."
Rutskarn avenges Josh screwing with them by doing a dramatic reading of the wikipedia article on the reproductive organs of male reptiles.
Mass Effect 2, Episode 10 comes in with the group realizing that Mordin has apparently grown tired of Josh's struggling through the previous episode and has single-handedly cleared a room normally filled with infinitely respawning enemies.
After one of the many times Josh reloads in Mass Effect 2, Mumbles and Rutskarn imitate giddy schoolgirls obsessing over Garrus.
Josh: I'm not cutting this.
Season 5, Episode 46 was a goddamn goldmine for these.
Rutskarn: "Would you like for me to predict your behavior minutely down to every tiny and embarrassing detail, or do you want me to have security cameras in your house? Because we can't have both, Mumbles."
"I'm so glad you could take time out of your busy schedule to teach a lonely Antlion how to fly."
From the Half-Life 2 playthrough, we get this gem as Josh gets stuck in a staircase battling a headcrab zombie with his gravity gun:
Josh: I need something to throw at this guy... But I don't seem to have... Shamus: Bullets. You have a machine that can throw bullets at him.
The clips from the failed attempt at playing the first Deus Ex on Shamus' computer during the Human Revolution playthrough.
Rutskarn I KNEW this day would come! I knew the day would come where cyborg satan whispered to me through Shamus' computer and tell me to kill Mumbles and stuff her body in a coffin with Shamus' audio card!
Deus Ex: Human Revolution provided one thanks to the interface, while sneaking.
Shamus: Are they launching space shuttles from here? What could possibly need this much infrastructure and support and this many personnel? I understand they had operations in the area, but... What required this level of complexity and involvement? Chris: ...Have you ever been to Detroit? beat Shamus: Ok, fair enough.
The murder mystery anniversary special is more or less non-stop snarking, with some particular gems sprinkled in.
Shamus: [Steam] Achievement unlocked: You are a pathetic waste of person. Why are you doing this? Go organize the icons on your desktop, you loser.
The original series is full of Hilarious in Hindsight moments. For instance, the swap from Josh to Randy because Josh was insufficently Chaotic Stupid, and the beginning of the fine tradition of Shepard catching rockets with his/her face.
The group imagining how they would behave if they were taken, in episode six of Alan Wake.
"I maKE pUns to aMUSE my FRIends."
During the 14th episode of Alan Wake, Chris at one point confuses Stephen King with Stephen Hawking. The rest of the crew start talking about how they could be playing the game as Hawking.
Again during Alan Wake, Josh (and some clunky collision detection) lead to Alan being visibly wounded by walking into a chair. Much merriment ensued.
The 8 by zombies stream included some hilarity courtesy of the contrast and overlap between the two streams. Team We Who Are About To Die were all irritable about facing down people with much more versus experience, while team Lions were swearing about being beaten up by the tank. Particular gems:
Rutskarn: Okay, Josh is kiting me
Josh: Where did the tank go?
The final FRAPS produced another one courtesy of editing:
Mumbles: This is all about Josh saying "oh look how awesome I am, beating up on noobs
quick montage of terrible, terrible things happening to Josh
The part where the pro team is just dicking around in the safe room at the start of the round.
Rutskarn: Alright, they're taking too long. That means they must have plans.
[cut to Glitch attempting to write "Spoiler Warning" on the walls, only to run out of space and forget the "i" in "spoiler"]
Following immediately on from this, Shamus imitating the Game, saying "Oooh, a stealth section. Okay, you're done with the turret, now I want you to sneak around." The way he says it has Josh asking if he's intentionally imitating SF Debris' Crazy Janeway voice.
Mass Effect 3, ep.11
Josh You know, this is a pretty heavy weapon, and it sets things on fire...
In episode 32 of the Mass Effect 3 season, Shamus got Josh back for all his trolling by declaring challange mode: say nothing negative about the game or company for the duration of the episode. The Thessia bossfight occurred in the episode. Note that Shamus was the only one who had completed the game, and so nobody else knew what was coming.
Rutskarn's "Assalt and battering" pun in The Walking Dead episode 2.
The group's discussion of the Ninja-Zombies in ep. 22 of The Walking Dead, resulting in Rutskarn getting out-punned by Shamus.
In the Dishonored playthrough.
Josh is trying to kill both Lady Boyle and the creepy nonlethal-option questgiver/stalker. He eliminates Lady Boyle after having difficulty with rampant AI, and finally approaches the stalker in the boat.
Josh (Throws whale oil at the boat) Here, I stuffed her inside this little bottle-
(Whale oil explodes)
Everyone (Laughter and amazement at the absurdity)
Bonus points as that option is perhaps the most creative and morally right way to end the mission.
Reginald Corvo spends the entire time he's supposed to grow weaker due to being poisoned throwing a tantrum and beaning everyone in the conspiracy with beer bottles with nobody reacting.
Josh also accidentally killed Sokolov by beaning him with an empty bottle. The delayed reaction before everyone realises what happened is hilarious, especially when taking into account Rutskarn's discussion on how Josh's antics would make a cutscene look.
Any time Rutskarn points out an obvious tone problem and Shamus/Chris responds with 5 minute long deconstructions.
During the Tomb Raider 2013 season, Lara's big Badass moment by grabbing a grenade launcher and going to town on the evil cult while screaming "RUN YOU BASTARDS!" while swelling music plays in the background was slightly undercut by Josh's repeated dying during the sequence. After the sixth or seventh go the whole thing had gotten hilarious rather than badass.
In the sixth episode of Metro 2033, Josh meets up with Khan and enters into the dark and spooky ghost-filled tunnels- only for Rutskarn to make "con" puns over and over. Then Shamus joins in.
Shamus: I feel really bad(THIS IS A LIE I REGRET NOTHING) about how this episode turned out.
The final Metro2033 video has Shamus suggest that a licensed version of The Stanley Parable be made by Marvel, and that it should be called the Stan Lee parable. He then goes into a hilarious Stan Lee impression.
The Fourth Anniversary play of Amnesia: A Machine for Pigs is almost wall-to-wall hilarity, between the numerous Call Backs, Josh abusing the physics engine, Mumbles' sexist jokes about pig bottoms, Campster tempting Rutskarn to dig up the male reptile reproduction article again, and the grand finale of riding the pigman.
Campster: ...I can't tell you a wikipedia article summary like it's a ghost story, I just can't. Rutskarn: Do you need me to tell you about hemipenes, Campster? Because I can tell you about hemipenes... Campster: ...What are hemipenes? Shamus:NOOOOOOOOO! Don't tell me about hemipenes, daddy!
Mumbles insisting that pig butts look identical to human butts, and subsequent argument with Campster over Google Image Search:
Mumbles: Okay, Campster, take your fingers and cover up the tail, and cover up the legs, and just look at the crack, and it looks just like a human butt!
Campster: Yeah, but, that's not where the rectum is.
Mumbles: We're not talking about the rectum, we're talking about the cheeks!
Campster: Okay, but cheeks have nothing to do with the butt!
Mumbles: HOW DARE YOU! The cheeks are most of what make butts GREAT! THAT'S THE WHOLE POINT OF BUTTS!
Shamus' reaction every time the word "Rectum" is used.
Shamus: I didn't think that I would need to announce this rule, but one of the rules on this show is that you're not allowed to use "the R-word"! I'm sorry, I- I didn't think it would come up!
The ending, with Josh once again jumping on the monster's head
The first episode of Skyrim, where Josh continues the proud Spoiler Warning tradition of Goomba Stomping the monsters.
The majority of Skryim episode 6, after Josh goes on a completely pointless killing spree. He tries to get rid of the bounty by having Balgruuf appoint him Thane, and then tries to recruit the help of the Companions. Both attempts fail, as Balgruuf and the companions all start attacking him, and he is killed by an angry mob of guards and companions.
The climbing song from The Stinger of Skyrim episode 9.
In Skyrim episode 15, Rutskarn goes into his Barack Obama impersonation.
In Skyrim episode 20, the crew install a sweetroll as jarl of Windhelm, who is sadly assassinated in his prime by being sat on by Ulfric.