Top 10 Video Game Moments that Will Make You Feel Hilariously Bad for Certain Characters

The Top Ten
1 Becoming trapped inside Crash's brain and thus surrounded by infinite festively dancing copies of his own hated archnemesis - Neo Cortex (Crash Twinsanity)
2 Having to do a wide assortment of agonizing things to himself, such as burn himself alive and crush himself into a pancake, in order to solve puzzles - Wario (Wario Land 2-4)
3 Becoming stranded on space debris with Orbot and Cubot for a much longer time than any reasonably mature person, let alone him, could feasibly tolerate - Eggman (Sonic Colors)
4 Being eaten alive by Hades and having to listen to the arrogant douche snark at him every five seconds while desperately struggling to escape his alternate-dimension-sized stomach - Pit (Kid Icarus Uprising)
5 Having to explore an entire area aptly titled "Pooland" - Conker (Conker's Bad Fur Day)
6 Being puked all over at least five times by a giant deformed caterpillar and forced to singlehandedly "rock" an entire nursery flood's worth of babies to sleep, then being puked all over yet again - Lammy (Um Jammer Lammy)

That is just low.

7 Basically any conversational activity you could theoretically have with him - Burgerpants (Undertale)
8 Being stranded on an asteroid for god-knows-how-many years with Lawrence - Dr. Nefarious (Ratchet & Clank)
9 Kazuichi completely giving up on subtlety and forcefully begging her to satiate his S&M fetish during a public court trial, as if the way he comically stalked her in general wasn't already bad enough - Sonia (Danganronpa 2)
10 Accidentally locking himself in the Absolutely Safe Capsule for all eternity - Porky (Mother 3)
The Contenders
11 Being turned into a potato by Wheatley about halfway through the game - GLaDOS (Portal 2)
12 Being swung/thrown about and even used as a snowboard by his own hated archnemesis - Neo Cortex (Crash Twinsanity)
13 Wario's Nuclear Fart - Everyone Besides Wario (Super Smash Bros. Brawl)

I was very creepy out

14 Being sucked into black holes, falling endlessly into deep space and god-knows-what else on a fairly regular basis - Mario (Super Mario Galaxy)

I believe you are referring to bowser, who has taken this punishment, and things beyond.

15 Being hit so hard from behind by King Dedede's hammer that it sends him flying nearly into outer space - Luigi (Super Smash Bros. Brawl)

I didn't feel bad at all. it's what he gets for being scared of an innocent looking thing. also I main dedede

16 Becoming stranded in space forever with the Space Core - Wheatley (Portal 2)
17 Also having to inflict cartoonishly agonizing injuries on himself in order to solve puzzles - Mummy (Sphinx And The Cursed Mummy)
18 Riding them around and then violently gnawing their heads right off - FBI Agents (Alien Hominid)
19 Watching her accidentally burn her entire house down in the process of attempting to cook spaghetti - Undyne (Undertale)
20 Being forced to singlehandedly pilot a broken airplane by using the flight lever as a guitar while the clinically insane former pilot screams loudly in her ear - Lammy (Um Jammer Lammy)
21 Genocider Syo's stalker-like obsession with him all throughout the game - Byakuya Togami (Danganronpa 1)
22 Being executed by being literally churned into organic butter - Mondo Oowada (Danganronpa 1)
23 Being constantly teased and belittled at every possible opportunity by Palutena, Viridi and Hades - Pit (Kid Icarus Uprising)
24 The infamous Milkman Conspiracy level - Boyd Cooper (Psychonauts)
25 Being locked in an inescapable prefab room for long enough to actually forget what "apple" means - Chell (Portal 2)
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