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

If you thought Jabba The Hutt and more recently the infamous Globglogabalab 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
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, 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 ...more
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)

Basically the game's official "Darker And Edgier" tonal-shift indicator, the abandoned asylum section (in laymen'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 suburbian descent into madness for yourself, preferably through extremely liberal usage of clairvoyance.
Basically all of the previous executions performed together in sequence (with her laughing and grinning ear-to-ear like the mentally deranged Looney Toons character she is the whole entire time, no less)
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)
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.
This is like, the only one I knew on this entire list. But yea, I was fighting one and Leon's head kept getting chopped off and the stupid noise the Garrador made made me laugh and my sister was like, "Why are you laughing, you just killed him!" And I'm like, "No, not that. The other thing is funny, lol)

