* The ''Insane Cafe'' [=RP=] trilogy has elements of this. The first was a nonsensical, hilarious and downright {{Narm}}y. The second was more plot driven and a terrorist attack on a remote laboratory was a key plot point. The 3rd installment features several assassination attempts, [[HotterAndSexier a few sex scenes]] and an impending war. Oh yeah, profanities are uttered the second and third installments.
* Website/{{Cracked}} has commented on the "gritty reboot" trend several times.
** An early Photoplasty: [[http://www.cracked.com/photoshop_103_if-hollywood-decided-to-give-everything-gritty-reboot/ If Hollywood Started To Give Everything a Gritty Reboot.]]
** Here's [[http://www.cracked.com/blog/4-gritty-reboots-80s-cartoons-girls/ some]] [[http://www.cracked.com/photoplasty_139_if-history-got-gritty-reboot/ more]].
** "[[http://www.cracked.com/blog/3-movies-they-dont-make-anymore-but-really-should/ 3 Movies They Don't Make Anymore (But Really Should)]]" decries the trend of "taking popular, existing properties and bringing out the darkest and grittiest aspects they can find" seen in ''Film/HanselAndGretelWitchHunters'', among other movies.
** "[[http://www.cracked.com/quick-fixes/4-bizarrely-specific-rules-fairy-tale-adaptations-all-follow/ 4 Bizarrely Specific Rules Fairy Tale Adaptations All Follow]]", David Christopher Bell claims that all film adaptations of fairy tales invoke this to invert {{Disneyfication}}.
* Just google "Misery Machine", possibly adding "Scooby Doo." D&E, textbook case.
* ''ThereWillBeBrawl'' makes the Creator/{{Nintendo}} universe ''so'' grimdark and FilmNoir-esque that it practically becomes a parody of this trope.
* The blog Chocolate Hammer mocked this trend with the game ''Darker and Edgier'', in which familiar franchises were warped beyond recognition and readers had to guess what they originally were. The posts in question can be found [[http://www.chocolatehammer.org/?p=91 here]] and [[http://www.chocolatehammer.org/?p=400 here]].
* "I'm going to ask you one more time! [[http://www.youtube.com/watch?v=PYhodCCUyBs Where the F*** is Carmen Sandiego?!]]"
* In [[TheRandomverse Marvel/DC: After Hours]] Season 2, SelfDemonstrating/TheJoker's plan is to make all comic book characters into DarkerAndEdgier characters. The Green Goblin however ends up pointing out that all that will lead to is DarknessInducedAudienceApathy without LighterAndSofter heroes.
* While most of the campaigns in the ''GlobalGuardiansPBEMUniverse'' were standard BronzeAge fare, the ''Night Life In The Big Easy'' campaign, which featured a solo 1980s-style vigilante facing off against a voodoo-themed criminal empire that had been built on drugs, prostitution, and white slavery, was straight out of the DarkAge.
* ''Website/CollegeHumor'' has a video illustrating the gritty reboot process: http://www.collegehumor.com/video:1935593
* [[http://www.youtube.com/watch?v=Kk9oa_PiXAk The Brothers Mario]] is a GTA Machinima with Mario and Luigi being mobsters involved in a gang war.
* [[http://www.youtube.com/watch?v=kg4ztJ32iPI&playnext=1&list=PL950DBC7AA9CA1B7E The Waldo Ultimatum]]. 'Nuf said.
* ''SuburbanKnights'' compared to ''WebVideo/{{Kickassia}}''. While both are hilarious and ''{{Kickassia}}'' indeed showed off Critic's lack of sanity well, SK had a really dark villain that made the mood drop in whatever scene he was in, innocents getting blown up, a BittersweetEnding where Critic hopes to find the Necronomicon in order to revive [[spoiler: Ma-Ti]], death not being at all cheap and actual, honest-to-God {{Tear Jerker}}s.
** In a more meta sense, WebVideo/TheNostalgiaCritic both in-character and out-of-character openly hates this trope when done poorly and, as he puts it, is "dark for the sake of being dark" instead of being dark to convey some message or have some purpose. It comes up in a good amount of reviews.
** ''WebVideo/ToBoldlyFlee'' manages to be even darker than ''WebVideo/SuburbanKnights''. The story revolves a ''literal'' PlotHole that warps and distorts reality. Highlights include WebVideo/TheNostalgiaChick and WebVideo/ToddInTheShadows [[spoiler: facing UnwillingRoboticization and brainwashing at the hands of [[WebVideo/AtopTheFourthWall Mechakara]]]], WebVideo/TheCinemaSnob [[spoiler:being manipulated into joining the villains, which, while a parody of Franchise/StarWars, is still pretty messed up]], the appearance of [[spoiler:Doug Walker (as in [[AuthorAvatar the actual person]]) revealing to the Critic he's a fictional character and that in the real world there's free will]] and finally the Critic, after a long HeroicBSOD that was completely PlayedForDrama, [[spoiler: [[HeroicSacrifice sacrificing himself]] by [[AscendingToAHigherPlaneOfExistence merging with the Plot Hole]]]]. Possibly justified, as according to WordOfGod ''To Boldly Flee'' was written be a send-off to The Nostalgia Critic as a show.
* When compared to the movies, ''TheGunganCouncil'' is ''definitely'' more mature across the board. However, whether or not it beats out StarWarsLegacy depends on the writer and character.
* The flash series ''WebAnimation/MarioBrothers'' was much darker than the original games, as the very beginning had Mario trying to escape from something before it proceeds to a flashback.
** Luigi ended up killed during an ambush on King Koopa's forces, Koopa successfully kidnaps Princess Toadstool because Mario was busy mourning for Luigi. Koopa's plans with Toadstool involve using her to create mushrooms so he could effectively be immortal. After a final stand against Koopa, and successfully dethroning him, he ends up ''failing'' to save the Princess (resulting in her death by magma alongside Koopa), and the direct result was an eruption, getting to where the series started. Mario then faces the magma flow and dies.
* "Zest Online Riddle" is a game similar to NotPron, and it's... weird. It also has dark, oppressive music and, overall, it's... creepy. Thing is, unlike most online riddles, this actually has some kind of a story to it, and from what this troper knows, it appears to be darkening "The Wizard of OZ", among other things.
* EquestriaChronicles is WesternAnimation/MyLittlePonyFriendshipIsMagic [[XMeetsY meets]] Literature/NineteenEightyFour.
* TwilightOfEquestria spins off from WesternAnimation/MyLittlePonyFriendshipIsMagic into a different world, one that is oh so much more sinister. Characters have contended with [[ZombieApocalypse zombie attacks]]. [[OurDemonsAreDifferent Demon ponies]] and [[HybridMonster hybrid ponies]] fraternize with mutant ponies and your usual [[FantasyKitchenSink unicorns, pegasi, griffins, and zebras]]. Heroes from [[IncorruptiblePurePureness the really good]] to [[GreyandGrayMorality the ambiguous]] grapple with {{Villains}} and [[AntiVillain Anti-Villains]] as they all try to understand what brought them together in the most unlikely of places...
* In FunnyOrDie's [[http://FunnyOrDie.com/m/6h0b The Rugrats ''Live Action'' Movie]] apparently Angelica is not just a selfish, spoiled child, but a murderous, manipulative sociopath.
* Parodied by TheOnion, with [[http://www.theonion.com/articles/general-mills-gives-honey-nut-cheerios-bee-intense,28181/ this]] ([[PoesLaw fake]]) story about a cereal mascot getting a dark backstory.
* For ''WebVideo/YuGiOhTheAbridgedSeries'', compare ''Yu-Gi-Oh: The Abridged Movie'' and ''Yu-Gi-Oh: Tenth Anniversary Abridged Movie''. While both are still quite funny, the latter has a greater amount of violence, more blue jokes (courtesy of [[Anime/YuGiOhGX Jaden]]), and an actual TearJerker with the retention of [[spoiler: the death of Yugi's grandfather]].
** It's worth noting, though, that the latter is immediately defused by "[[MoodWhiplash Can I have my Oscar now?]]"
* A bit of an overlap with the Advertising section, but someone [[http://i.imgur.com/3DdGA.jpg created this]]. Extremely dark, gritty, and honestly depressing, until you get near the end... [[spoiler: [[MoodWhiplash OOOOOH YEAH!]]]]
* While the original {{WebOriginal/Ghost_K}} (Order of the Guardians) setting is a standard [[AlienInvasion Alien Invasion]] Sci-Fi story with [[ElementalPowers elemental heroes]] fighting them, it has spawned a much bleaker prequel series in the form of K21 Sqaured. Here the enemies are entirely human, with an array of disturbing goals. Elemental power is abused more readily as it not seen as a blessing like it is in Order of the Guardians storyline.
** The collection of short stories that compromise the Subterfuge Chronicles and Shattered Endeavours manage to be Darker and Edgier than even the main K21 Squared storyline, with the majority of the stories set from the perspective of antagonists. Tarnished Perceptions also manages this, but is arguably more in line with the way in which the main story is portrayed.
** Second Great Battle of Siberia is this to the main Ghost_K setting, as it provides a more futile depiction of the efforts of humanity to defeat the aliens [[spoiler: with all of the main characters managing to die in the process]].
* Creator/RaymondSipe has a song about {{Cthulhu}} that [[http://www.youtube.com/watch?v=DLFHFWK5FJM pretty much does justice to its source]]. However, when you compare it to songs about forum places like /v/, /mu/, and even /mlp/, as well as many of his other songs he's done, and it makes its darker and edgier motif all the more surprising to see.
* Before its first, and original cancellation, Ben's Rants were very tame. The worst that WebAnimation/{{Benthelooney}} would put in was alternatives for curse words. However, when he uncancelled his rants in 2012, Ben Tannehill started writing in more personality for the character, and made him more cartoony, causing for the newly produced rants to include references to violence, and occassionally, sex. Whilst these aren't as bad as some, it is still raunchier than anything that Ben did, before the rants were resurrected.
** Not only that, but in the credits of Ben Rants: Sanjay and Craig, the song has an uncensored swear word. Ben stated that the reason for not censoring it was because he refused to censor such an awesome song.
* French artist Sylvain Sarraulh's [[http://tohad.deviantart.com/gallery/26155946 Badass versions of cartoon characters]].
* ''WebVideo/PokemonApokelypse'' parodies this by making the world of Pokemon dark and edgy.
* ''Wiki/TVTropes'': DarthWiki is where all the negative opinions go to. And a couple of other dark stuff.
* ''WebVideo/DragonBallZAbridged'', while still being mostly comedic, seems to be diving into this with the Cell Saga, specifically around the time when the BigBad himself is introduced. The fact that Cell's presence is, unlike all the other villains who appeared in the series prior, actually treated with complete seriousness by the cast should be a sign of things to come.
* Coming soon to a theater near you: [[https://www.youtube.com/watch?v=TnpTcrtsN3U a dark and gritty live-action adaptation]] of ... [[WesternAnimation/DoratheExplorer Dora the Explorer]].
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