Darker and Edgier/Web Original

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• The Insane Cafe RP trilogy has elements of this. The first was a nonsensical, hilarious and downright Narmy. 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, a few sex scenes and an impending war. Oh yeah, profanities are uttered the second and third installments.
• In Cracked.com:
  • Photoplasty: If Hollywood Started To Give Everything a Gritty Reboot.
  • Here's some If History Got a Gritty Reboot.
  • "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 Hansel & Gretel: Witch Hunters, among other movies.
  • In "4 Bizarrely Specific Rules Fairy Tale Adaptations All Follow", David Christopher Bell claims that recent film adaptations of fairy tales invoke this to invert Disneyfication.
• Just search the web for "Misery Machine", possibly adding "Scooby Doo." D&E, textbook case.
• There Will Be Brawl makes the Nintendo universe so grimdark and Film Noir-esque that it practically becomes a parody of this trope.
  • Uh... It is a parody of this trope.
  • It's an Indecisive Parody. A lot of the melodrama may be exaggerated beyond belief, but the series still is able to (in complete sincerity) create the kind of drama that Darker and Edgier revisions are supposed to evoke in the first place.
• 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 here and here.
• "I'm going to ask you one more time! Where the F*** is Carmen Sandiego?!"
• In Marvel/DC: After Hours Season 2, The Joker's plan is to make all comic book characters into Darker and Edgier characters. The Green Goblin however ends up pointing out that all that will lead to is Darkness-Induced Audience Apathy without Lighter and Softer heroes.
• While most of the campaigns in the Global Guardians PBEM Universe were standard Bronze Age 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 Dark Age.
• College Humour has a video illustrating the gritty reboot process: https://web.archive.org/web/20100527233356/http://www.collegehumor.com/video:1935593
• The Brothers Mario is a GTA Machinima with Mario and Luigi being mobsters involved in a gang war.
• The Waldo Ultimatum. 'Nuf said.
• Suburban Knights compared to 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 Bittersweet Ending where Critic hopes to find the Necronomicon in order to revive Ma-Ti, death not being at all cheap and actual, honest-to-God Tear Jerkers.
  • In a more meta sense, The Nostalgia Critic 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.
• When compared to the movies, The Gungan Council is definitely more mature across the board. However, whether or not it beats out Star Wars Legacy depends on the writer and character.
• The flash series Super Mario Bros was actually 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 Bowser's forces, Bowser successfully kidnaps Princess Peach because Mario was busy mourning for Luigi (and it is heavily implied that several of the Toads ended up killed in the assault). Bowser's plans with Peach involve using her to create mushrooms so he could effectively be immortal. After a final stand against Bowser, and successfully dethroning him, he ends up failing to save Princess Peach (resulting in her death by magma alongside Bowser), and the direct result was an eruption, getting to where the series started. Mario then faces the magma flow and essentially 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 hell out of "The Wizard of OZ", among other things.
• Equestria Chronicles is My Little Pony Friendship Is Magic meets Nineteen Eighty-Four.
• Twilight of Equestria spins off from My Little Pony Friendship Is Magic into a different world, one that is oh so much more sinister. Characters have contended with zombie attacks. Demon ponies and hybrid ponies fraternize with mutant ponies and your usual unicorns, pegasi, griffins, and zebras. Heroes from the really good to the ambiguous grapple with Villains and Anti-Villains as they all try to understand what brought them together in the most unlikely of places...
• In Funny Or Die's The Rugrats Live Action Movie ^{[dead link]} apparently Angelica is not just a selfish, spoiled child, but a murderous, manipulative sociopath.
• Parodied by The Onion, with this (fake) story about a cereal mascot getting a dark backstory.