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By that I mean the show has all the stereotypical anime staples, y'know kawaii desu katanas 4 life oops upskirt power of love. I'm looking with a show where the main character(s) is aware of all those and despises it all.

I'm talking a character who, when confronted with teenage Mary sue swordsmen drenched in hot topic goes "fuck my life" and goes against every animu convention he or she can find.

Any suggestions?

Yahari Ore no Seishun Love Comedy wa Machigatteiru.

Edit: Nice try coolface. Now go back to RR.

Ouran High School Host Club is my best suggestion fitting this criteria. It's just dripping in shoujo/romance anime stereotypes and self awareness. It's truly one of my favorite anime, it's just so god damn hilarious.

You could give The Devil Is A Part Timer a try. It doesn't so much make fun of anime tropes as much as it puts them in an unfamiliar scenario. For example there's the whole battle between good and evil thing but the supposedly evil character isn't actually that bad. It's on Netflix so give it a try.

And although it doesn't entirely fit your criteria you could also try The Melancholy of Haruhi Suzumiya. Throughout the series the character Haruhi is attracted to various things because they're cool and fit anime tropes (like recruiting a club member for no other fact than she's moe). The main character Kyon thinks this is ridiculous and often makes sarcastic remarks about her motivations.

I can't claim that this show fits your criteria to a T, but if you're looking for a really cynical comedy anime, you really need to watch Humanity has Declined. That show has such a bitter sense of humor, and it is so funny because of it.

The Melancholy of Haruhi Suzumiya is a closer one to what you are looking for, but it's a bit hard to jump into because since they originally aired the episodes out of order it becomes very inaccessible. If you can find a collection that is in Chronological Order including the 2nd Season and Skip the Endless 8, go for it.

And this definitely doesn't fit, but the first episode of Tower of Druaga. Yeah, just the first episode. Takes getting married when you get home deaths to power up the hero to the extreme.

To narrow the selection i'll posit a scenario:

Take Guts, slap him in sailor moon and watch him go to town.

Anything like that?

>sailor moon

I think it would had been better if you mentioned Hidamari Sketch or K-On instead of Sailor moon. Though there is a Light Novel involving some dude with a Twintail fetish that has been recruited by twintailed aliens to help them and became a twintaled girl…But you're probably not looking for that

Ehh I guess I was off on calling what I'm looking for "self-aware" anime cuz I didn't know what else to call it.

What I meant by the scenario is I wanna see a character as dark and fucked up as Guts tearing shit up in a relatively light-hearted stereotypical anime atmosphere. I don't remember much of sailor moon from my childhood so I don't know if it's that applicable to the aforementioned atmosphere.

I mean, I think I know what you are getting at, but how the hell are you going to have a plot if you have some crazy guy rampaging all over some friendly world? It seems like you would just put something dark in something light for the sake of it.

From this, I'm guessing you don't want those "cynical" type of stuff people were mentioning. I think what you're trying to say is a "what if something our guy basically sees some other people talk about power of friendship and love, and then beat the shit out of him and calls it bullshit."

The reverse of what you're asking has been done (Instead of guts in sailor moon, its like sailor moon in Beserk, I guess) in which certain perception of cute genres are taken in dark direction, but I don't think that's what you're looking for.

I'll say that what you want might not exist, but there is a shitload of anime there, so I don't know. I'll say that I'm pretty sure there would be some manga that fits what you're looking for.

Gin Tama might fall into this category the way it constantly breaks the 4th wall, parodies various tropes seen in anime, makes fun of other anime (there's one episode where they say they're going to make a crossover movie featuring the cast of Gin Tama called DragonBleaPiece, which is a parody of Dragon Ball, Bleach and One Piece) and not taking itself seriously about 75% of the time.

That's a pretty tough thing you're looking for by the sound of it.

I'd say the closest thing I can think of would be Madoka Magica which takes a traditionally light genre (magical girl genre) and puts it in a dark scenario. But that's more of a deconstruction of the genre rather than a parody or comedy. I think I might have to agree with sniper and say that what you're looking for may not exist.

I'm watching Senyuu, it's pretty self aware about how ridiculous it is. It's about a hero who everyone mocks going off to defeat a demon king and getting caught up in ridiculous situations.
It's made up of a bunch of short 5 minute animations