Top 10 Video Game Moments that are Both Funny and Terrifying at the Same Time (Spoiler Warning)

The Top Ten
1 Meet The Pyro trailer from Team Fortress 2

Heavy: "I fear no man, but that... THING... it scares me..."
Spy: "One shudders to imagine what inhuman thoughts lie behind that MASK... what dreams of chronic, sustained CRUELTY..."

Pyro: (Hallucinating himself dancing through an even cuter version of Equestria and blowing bubbles and rainbows at adorable baby versions of the opposite team's members, while his real-life self burns the opposite team's entire fortress to the ground with his flamethrower and psychotically, brutally murders every single one of its members with literally no remorse.)

2 The Great Mighty Poo's Opera Concert from Conker's Bad Fur Day

If you thought Jabba the Hutt and more recently the infamous Globglogabgalab monster were disturbing... well, to put it simply, while this guy may indeed have one of the most beautiful singing voices that has ever been blessed upon humanity's mortal ears, his body is something that I literally would not even touch with Thurl Ravenscroft's fabled thirty-nine-and-a-half-foot pole.

3 "After-School Sale" and "Fright Flight" stages from UmJammer Lammy

In the former stage, our dear mentally deranged and incredibly sexy random-object-as-guitar-shredding anthro-paper-cutout sheep (girl)friend gets inflated into a hideous Deviantart abomination of herself. She gets trampled by a massive parade of expectant rabbit mothers (with rather uncomfortably visible cleavages to say the least, at that) and is repeatedly (rainbow) puked all over by a giant midwife caterpillar (with the personified voice of cancer itself) who mistakes her for pregnant and therefore drags her into the mall by hand.

Where she then has to calm an entire flood of rabbit babies by literally rocking them to sleep in the process (again, by literally using one of them as a guitar). All the while, an entire-screen-filling psychedelic wave of multicolored caterpillar segments and slimy green baby-holding hands surges through both the foreground and the background.

And believe me, it doesn't really get any less creepy from there. In the stage immediately after that one, she ends up having to help a mentally deranged, long-retired Air Force pilot with a downright horrifying case of Jekyll-and-Hyde syndrome fly his own broken-down airplane (by using its assistant flight lever as a guitar, proving that she herself is easily just as insane as he is), which she deliberately crash-lands right in the middle of a fully-loaded drive-in movie theatre parking lot, effectively killing everyone there. And then, just to put the icing on the creep-factor cake, she ends up getting the pilot's dentures as the visual representation of her next guitar-effector accessory. Yeesh.

4 Meeting the Seamen in Seaman for Dreamcast

Overtly human-faced alien mutant angler fish with the voice (actor) and personality of Spock from Star Trek - enough said. And just in case that wasn't enough, they also very insistently want to learn basically everything important that there is to know about you and your collective families so that they can one day unite to take over the entire world.

5 The Milkman Conspiracy from Psychonauts

Basically, the game's official "Darker and Edgier" tonal-shift indicator, the abandoned asylum section (in layman's terms, the last third) of Psychonauts, in addition to finally being the point when the game almost starts getting legitimately good in the gameplay department, is also absolutely horrifying in a whole number of different ways.

Sadly, the endgame Meat Circus level is far too purely horrific and disgusting to include this high up on the list, so I'll just have to settle for this instead.

While the asylum itself is already plenty bad enough (especially in terms of its structural condition), the mind of its former police officer entrance guard, Boyd Cooper, is more-than-arguably even worse.

Honestly, it's the one thing on this list that I'm actually not going to spoil for you. Seriously, just witness the Milkman's literally twisted suburban descent into madness for yourself, preferably through extremely liberal usage of clairvoyance.

6 Encountering the Magypsies in Mother 3
7 Junko's suicide in Danganronpa: Trigger Happy Havoc

Basically, all of the previous executions performed together in sequence (with her laughing and grinning ear to ear like the mentally deranged Looney Tunes character she is the whole entire time, no less).

8 Crocomire attempting to continue fighting Samus as his own crumbling skeleton after having all of his flesh melted off by boiling-hot acid in Super Metroid

Lame and stupid boss fight, unforgettably epic and amazing death sequence.

(Also more-than-likely a parody of how Mario canonically "kills" Bowser in Super Mario Bros., as well as the infamous Dry Bones enemy from Super Mario Bros. 3 and Mario World.)

9 Golden Diva Battle from Wario Land 4

From the opening cutscene where she literally snorts an entire cat up her nose via an alien tractor beam, to the ridiculous number of hilariously various facial expressions, kabuki masks she wears stacked together to hide her repulsively ugly real face, to the especially traumatizing moment when her true face is revealed, and finally, her being reduced to just her lips once Wario wears her down to her very last hit point, there is not a single dull moment in this fight.

10 Captain Quark publicly demonstrating the nether-region-cleaning functions of his Personal Hygienator on live television in Ratchet & Clank
The Contenders
11 GLaDOS "pretending" she's going to murder you in cold blood in Portal
12 Fighting the Garradors in Resident Evil 4

This is like, the only one I knew on this entire list. But yeah, I was fighting one, and Leon's head kept getting chopped off and the stupid noise the Garrador made me laugh. My sister was like, "Why are you laughing? You just killed him!" And I'm like, "No, not that. The other thing is funny."

13 Zelda CD-i Cutscenes
14 Wheatley taking over Aperture in Portal 2
15 N. Gin threatening to delete your save file if you lose against him in Crash Bandicoot: Warped
16 Playing with Endogeny in Undertale
17 Handsome Jack's spoon monologue from Borderlands 2
18 When Kazuichi develops his insane stalker obsession with Sonia in Danganronpa 2: Goodbye Despair
19 Burgerpants' facial expressions in Undertale
20 When Cortex finds himself trapped inside his own arch-nemesis' brain in the ending of Crash Twinsanity
21 SA-X's transformation in Metroid Fusion
22 Correx cross-dressing himself as Coco Bandicoot in Crash Twinsanity
23 Encountering Master Belch in Earthbound
24 Meeting Porky in Mother 3
25 Papyrus' Genocide death in Undertale
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