!As this is a Funny Moments page, spoilers ''will'' be left unmarked. Administrivia/YouHaveBeenWarned!
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[[quoteright:258:https://static.tvtropes.org/pmwiki/pub/images/iwbtg_lubu_3.jpeg]]
''VideoGame/IWannaBeTheGuy'' is a [[PlatformHell fiendishly difficult game that loves to troll the player at every turn]]--so hard, you might find yourself [[CrossesTheLineTwice going from screaming in frustration to laughing...and maybe back to screaming, then more laughing]].
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* The fact that, for absolutely no logical reason, touching a ''fruit'' will turn the Kid into a shower of blood and guts. And that's before the fruit falls ''[[SelectiveGravity up]]'' to kill you.[[note]]And remember: They're not apples. They're more like giant cherries.[[/note]] And then there's Kayin's explanation: the fruit is so deadly that it has to be boiled three times to remove all the poison, and if you only boil it twice, it turns into a bouncy orb of death as shown in the ''Breakout'' section.
* The boss battle with Dracula replicates the prologue dialogue from ''VideoGame/CastlevaniaSymphonyOfTheNight'' word-for-word, with The Kid replacing Richter. And then... [[PressXToNotDie he throws his wine glass at The Kid, killing him if he doesn't dodge it in time.]]
** And the ending of that battle.
--> [[VideoGame/CastlevaniaSymphonyOfTheNight BEHOLD]] [[{{Dracula}} MY]] [[OneWingedAngel TRUE FORM,]] [[LargeHam AND DESPAIR!!!]] *[[ClippedWingAngel Turns into]] [[Franchise/{{Kirby}} Waddle Doo]]*
* Also, [[VideoGame/TheLegendOfZeldaI It's dangerous to go alone! Take this.]] '''[[YetAnotherStupidDeath YOU JUMPED INTO A SWORD. YOU RETARD/DUMBASS!]]'''"
* The ending, which allows you to [[KaizoTrap die at the end of the credits]]. Probably not so hilarious if you discover it the hard way, though.
** Oddly enough, the spikes at the bottom '''don't''' kill you.
* Ryu from Franchise/StreetFighter coming out of absolutely nowhere and hurricane kicking the Kid into a pulp.
* The special death if Kraidgief gets hold of you: [[Manga/FistOfTheNorthStar Hokuto Shinken]] [[Franchise/StreetFighter Spinning Piledriver!]]
** Kraidgief. The sheer concept of Kraidgief is absolutely hilarious. It's simply what would happen if Kraid from ''Metroid'' and Zangief from ''VideoGame/StreetFighterII'' did the {{fusion dance}} from ''Manga/DragonBall''.
* The error box trap. Always funny to watch someone playing for the first time get hit with it.
* The funny music from ''VideoGame/MarioPaint'' that plays when you get hit by the airplane.
* "Die, monster!-! WHOZAWHAT? [[YouExclamation YOU]]?!"
** In the same cutscene:
-->'''The Guy:''' [[WhamLine No. Not The Guy]]. [[TheReveal The]] [[LukeIAmYourFather Father!]]
-->'''The Kid:''' '''[[BigWhat WHAT]]'''
** [[LukeIAmYourFather "Yes, I]] [[ParodiedTrope did have sex with your mother."]]
* Didn't escape the room with the VideoGame/{{Tetris}} pieces in time? A giant pill from ''VideoGame/DrMario'' smashes you and it fills the whole width of the playing field to boot!
* In a certain room before Kraidgief, there are some spikes at the bottom of a room, but they cover only a small part of the floor. You'd think you could jump off safely... and if you try, the spikes get up on their legs and place themselves ''right below you''.
* From the [[http://kayin.moe/iwbtg/old/faq.php old FAQ]]:
--> '''Q: [[YouMonster You're a bastard.]]''' \\
A: [[BluntYes Yes.]]
** The version from the [[http://kayin.moe/iwbtg/faq.html rewritten FAQ]] isn't too bad either:
--> Q: You're a mean, bad person!\\
A: I try to be nice!! I'm just trying to make a fun game for masochists! I have to help out my own kind.
* The room before the Tetris segment involves a [[VideoGame/SuperMarioBros2 Snifit]] manning a [[VideoGame/SuperMarioBros1 Bullet Bill]] cannon. Try to jump into the pit (leading to the Tetris room) without taking him out? He shoots a ''giant [[AlwaysAccurateAttack undodgeable]] {{death ray}}'' at you.
* After finishing The Maze of the Guy Castle segment, you will see a Bowser painting (this implies that he once had the Guy title previously, which kinda hilarious if you take a minute to think about it). but even more hilarious is the room after that painting - a totally badass character [[UsefulNotes/LuBu Lü Bu]] in the painting. Make sense, because of what he is capable of - except Bowser breathe fire and it goes into him, and turned this guy into what as you can see in the trope image above.