* Tails when he's flying over Prison Island.
-->'''Tails''' There's no mistake about it, This must be the island. It's a secret military base that is reinforced and super strong! It's called Prison Island. [[OpenSecret I heard the news about it on Satellite TV!]]
* There's the scene where Rouge strangles Knuckles and yells at him for breaking the Master Emerald into pieces.
-->'''Rouge:''' What was that all about?! And ''LOOK WHAT YOU DID TO MY EMERALD!''
** Eggman's only response to Knuckles shattering the Emerald is to flail about as if ''he'' got punched...and let out a slightly disinterested FlatWhat, before pretty much shrugging his shoulders and heading back to base.
** And before all ''that'', we have Rouge [[DullSurprise giving out one of the most half-hearted yells in recorded history]], which is also reused later in the game when she ''almost falls to her death''.
* Three words: Amy. [[TheGlomp Hugging]]. ''Shadow''. The look on his face is priceless. And you thought Rouge was terrifying.
* Sonic's delivery of the line [[OhCrap "BLOWS UP?!"]]
* ''Sonic Adventure 2'', in the Dark Story before the Egg Golem boss. We get almost the same cutscene as when you fight it as Sonic, but in this version Sonic [[http://www.youtube.com/watch?v=wXfs2nf4-Y0 jumps up and delivers a kick]] to the golem which breaks the restraining mechanism on it and causes it to turn on Eggman. Though it's more of the dialogue that makes this hilarious:
-->'''Sonic:''' TERIAAAAA!!!\\
'''Eggman:''' *When the Golem turns towards him* NOOOOOOOOOOO!
** Made funnier by the fact that if you listen to it with the Japanese audio, it becomes "TEEEEEERIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA!"
** Another funny moment, present in both versions:
--> '''Eggman''': "Gah, what a piece of junk!"\\
The Egg Golem looks to Eggman as the ImageSong says "don't criticize"
* [[http://www.youtube.com/watch?v=yj90a6S3vFc OH NO! DON'T TOUCH THAT LEVER!! OOOOOOOOUUUUAAAAAAAAAHHHHH!]]
** The dialogue immediately before that:
-->*the shuttle hits a stray meteor*\\
'''Sonic:''' "What the!?"\\
'''Tails:''' "Is everyone alright? We should be landing soon!"\\
'''Knuckles:''' Oh no...the hatch door is open!\\
'''Sonic:''' [[WhatAnIdiot Don't sweat it, Knuckles.]] The only in the cargo bay are those Master Emeralds! Right?\\
'''Knuckles:''' What do you mean, don't sweat it?! Land the shuttle and let me out!\\
'''Sonic:''' Knock it off, Knuckles! We're gonna crash this thing if you keep that up!
** And then later, Sonic telling Eggman that Knuckles piloting the shuttle was a lot more dangerous than Eggman could ever be.
* Sonic's recap of Crazy Gadget includes this line.
-->'''Sonic:''' Eggman said he'll trade us Amy for the Emerald... I have to think about that one!
* This exchange in the Last Story.
--> '''Eggman:''' That mad scientist!\\
'''Amy:''' [[HypocriticalHumor That should be you, right?]]
* After Shadow trashes The Biolizard in an epic one-on-one battle, he finishes with the greatest one-liner in the universe; [[ItMakesSenseInContext "GET OUT, YOU UGLY PROTOTYPE!"]]
* Omochao's reactions to getting hit can be pretty funny, especially when you weren't even the one who hit him and he still gets mad at you. Clearly, the programmers knew fans weren't gonna like him.
* Basically, any moment when you're playing as Eggman, and take damage, sometimes he says "You! I'll make you pay for this!" He will say this when he takes damage from enemy attacks, running into enemies, even when he [[ArsonMurderandJaywalking takes damage from a stage hazard, such as a spike, or a laser.]] What's funny there is the thought of him yelling at an inanimate object that didn't even intend to cause him any harm.
** '''[[MemeticMutation YOSH!]]'''
** '''[[LargeHam OH NO! My power is going down!]]'''
* Sonic's second encounter with Shadow is supposed to be serious, but one simple error made it absolutely hilarious:
-->'''Sonic''':I found you! Faker!\\
'''Shadow''': Faker? I think ''YOU'RE'' the fake hedgehog around here! You're comparing yourself to ME? Ha! You're not even good enough to be my f-\\
'''Sonic:''' [[InterruptingMeme I'LL MAKE YOU EAT THOSE WORDS!]]
** And speaking of which, just any time characters interrupting each other's sentence can qualify. Or hell, when Sonic speaks so fast he interrupts ''himself!'' "Hey! Its not his spee-he must be using the Chaos Emerald to wa-" "-name is Shadow."
* Eggman catching the nightly news at his hideout.
** "We interrupt this ''broadcawst'' for this ''impawtant'' news ''[[OohMeAccentsSlipping flawsh]]''."
** "Mysterio-YUSS-ly, the only thing stolen was-" "A Chaos Emerald???" "-a Chaos Emerald."
** "Eyewitnesses on the scene identified the culprit as world-renowned hero, Sonic the Hedgehog." (this said over a ridiculously high-quality shot of a black hedgehog with red eyes and white fur who looks absolutely nothing like Sonic.) [[CaptainObvious "Sounds more like the work of]] '''[[CaptainObvious Shadow]]'''!"
* Just the character's reaction to whenever a ghost pop ups from out of nowhere. They drop on the ground for a second and then get back on the ground again.
* Debuggers have found ways to put Mech-less Eggman in other stages, mainly Sonic and Shadow stages. This is already funny on it's own, but then people discovered what happens when [[http://orig04.deviantart.net/89be/f/2016/160/7/e/gif__eggman_gets_an_upgrade_by_the_driz-da5kxqe.gif he gets an]] [[http://i.makeagif.com/media/5-26-2016/fMsf3P.gif upgrade in this form]].
* Try to get behind King Boom Boo too early... over and over again. "Rrr hrr, rrr hrr! Hee ha ha ha ha ha ha ha!"
** Worse yet is the sound he makes when he first appears. " ''Blaar blaar blaar!'' "
* In EternalEngine, there's a room with [[AnnoyingVideoGameHelper Omochao]] in it. And he's right next to an airlock that can be blown up. Shoot at it, and [[VideoGameCrueltyPotential Omochao will be sucked out of the airlock and continually respawn]].
** Hell, any time VideoGameCrueltyPotential happens to Omochao is funny.
** The best ones are the ones that happen by accident such as when you're charging up a Spin Dash with the Light Attack obtained, or when a Laser Blaster powered shot explodes in its face. He just had to get into the action, didn't he?
** Omochao can break crates and robots just by [[LethalJokeCharacter accidentally flying into them]].
* Many of Big the Cat's cameos can be this, especially if you're not expecting them. Sometimes he's just climbing a wall, sometimes he's fishing for nothing, and sometimes he'll just...stare at you.
** His appearances in cutscenes are just a joy in and of themselves; if you can activate them, you can see Big chilling out in several plot important scenes. He's even in the G.U.N. helicopter at the start of the Dreamcast version!