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As this is a Funny Moments page, spoilers will be left unmarked. You Have Been Warned!

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I Wanna Be the Guy is a fiendishly difficult game that loves to troll the player at every turn—so hard, you might find yourself going from screaming in frustration to laughing...and maybe back to screaming, then more laughing.
  • 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 up to kill you.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 Castlevania: Symphony of the Night word-for-word, with The Kid replacing Richter. And then... he throws his wine glass at The Kid, killing him if he doesn't dodge it in time.
    • And the ending of that battle.
  • Also, It's dangerous to go alone! Take this. YOU JUMPED INTO A SWORD. YOU RETARD/DUMBASS!"
  • The ending, which allows you to 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 Street Fighter coming out of absolutely nowhere and hurricane kicking the Kid into a pulp.
  • The special death if Kraidgief gets hold of you: Hokuto Shinken Spinning Piledriver!
  • The error box trap. Always funny to watch someone playing for the first time get hit with it.
  • The funny music from Mario Paint that plays when you get hit by the airplane.
  • "Die, monster!-! WHOZAWHAT? YOU?!"
    • In the same cutscene:
    The Kid: WHAT
  • Didn't escape the room with the Tetris pieces in time? A giant pill from Dr. Mario 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 old FAQ:
    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 Snifit manning a Bullet Bill cannon. Try to jump into the pit (leading to the Tetris room) without taking him out? He shoots a giant 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 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.

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