Crapsack World/Web Original

• Tech Infantry is partly based on the Old World of Darkness, so of course it's a dark and pessimistic world, with an oppressive and corrupt government, genocidal aliens, ancient supernatural entities manipulating the unawakened human population for their own mysterious ends, and any idealistic characters quickly getting the hope kicked out of them by a callous and indifferent universe.
• In Vatsy and Bruno, the streets are strewn with garbage, the skies are grey, the protagonists are a pair of non-tax-paying vagrants whose only talents involve criminal acts and the organizations oscillate between ludicrously incompetent and outright murderous. It's a comedy.
• Star Wreck: In The Pirkinning.
• This is actually pretty common on Newgrounds, probably the ultimate example would be the featureless muddy hell of Salad Fingers.
• You can see a pretty good example of this on the SCP Foundation, a pseudo-governmental organization built around containing, securing, and protecting humanity from strange creatures, objects -- and people. This is all the more obvious in the roleplaying scenarios, where Agents, Doctors, and Beings are entitled to eliminate anything from the face of the Earth if it poses a significant, uncontainable threat. Or if it's a Mary Sue. Oh... and humans don't matter all that much more, personally speaking.
• In Underground Crushed Underground by sam512, what seems to be all of humanity is imprisoned in a giant underground arcology, doomed to toil until they die. The word "dystopia" is explicitly used. That's bad. It gets worse. They're trapped in the arcology because it's actually a giant fallout shelter, holding the only survivors of humanity. With the outside a radioactive hellscape, and the biosphere completely destroyed, it'll be another two thousand years before they can leave the arcology. The immortal Governor only kept it from the proles to keep the suicide rate down.
• There Will Be Brawl, which takes place in a massively Darker and Edgier version of the Mushroom Kingdom. You're either a petty criminal, an Obstructive Bureaucrat, or in the pockets of The Mafia. Or possibly all three.
• In the Colour My... Series, there's a long list of forbidden activities on the stick-figure citizens. Among these are pets, plants, running, emotion, color, and smiling. There are huge robots to enforce the laws, too.
• The entire universe in NationStates is basically this.
• In the universe of Addergoole and Wild One's Blood, the Ellehemaei are royally screwed by the Universe, since even casual promises are mystically enforced by "The Law." Oh, and if you manage to break free and defy The Law you apparently turn (more) evil. The Addergoole of the title is a Boarding School of Horrors where teenaged Ellehemaei, who at this point think they're human, are thrown in the deep end of their screwed up society.
• Foxforce. In this world there was no space race, no NATO, no UN, no Star Trek, no Live Aid, no Israel, no global vaccination programmes, no VE day, no 13th Amendment, and no Emancipation Proclamation. Science still marched on, but in new directions. Artificial intelligence and artificial life are both very real, and very sentient, and can be brought and sold online. Imagine, if you will, a world where organisations like PETA campaign not for the rights of animals, but the rights of slaves, and yet are held to the same level of contempt. This is the world of Firefox, Technofox, Silverfox, and (coming soon) Shadowfox.
• The world inhabited by the title characters of Lego Pirate Misadventures is pretty grim for a Lego world. Pirates apparently own at least one city, have an academy dedicated to learning the trade of raping and pillaging, and are ruled by a guild stuffed full of Obstructive Bureaucrats. This city also has a hit TV show called "Torture Time With Mr. Cuddles" where people get tortured to death, and people get gunned down in the street for little to no reason. No one seems terribly bothered by any of this, though.
  • Additionally, a world conquering League of Darkness was able to rise to power with absolutely no one noticing before it was too late, necessitating Gag's Set Right What Once Went Wrong gambit.
• The AlternateHistory.com timeline, For All Time, beginning with the death of Franklin D. Roosevelt shortly after Pearl Harbor, basically takes Finagle's Law and applies it to 20th-century history. In this world, all leaders are either corrupt, incompetent or insane, nations get splintered or thrown into civil war on a daily basis, and nuclear weapons get tossed around like snowballs.
• Dr. Horrible's Sing-Along Blog presents a world where the superheroes are superficial, anti-intellectual Jerk Jocks; the villains are evil/bad in their own ways; otherwise good kids who happen to be smart and/or odd are still inspired to become villains anyway because the bad guys are more accommodating; most people blindly worship the heroes and/or villains; and the truly good people trying to make a real difference get ignored and/or caught in the crossfire. Have fun!
• The future world from the ARG based around Nine Inch Nails' "Year Zero" album is a world where the US has become a repressive and insular theocracy following multiple chemical and biological attacks against it. US citizens are kept in-line via drugs in the public water supply and easily-available and highly addictive street drugs like "Opal" which come from government-funded pharmaceutical corporations. Global warming has made the equatorial regions of the planet nearly uninhabitable (and indeed has affected the climate enough that there is baseball being played outside in St. Louis in February). The rest of the world seems to be in a constant state of brush wars where American soldiers are kept on the knife's edge of psychosis with military drugs. The world is so crapsack that even visions of a god-like hand reaching down from the sky that cause electronics to fail and observers to go insane, might really be only a side-effect of easily-available government drugs, or just global hallucination brought on by the hopelessness of the real world.