In "'Durarara!}", the japanese city Ikebukuro is shown as an example, with a bunch of gangs around, people cutting each other with knifes, Shizuo throwing random vending machines at Izaya everywhere around the city, and a headless motorcycle rider going around, freaking people out and stuff. Lovely city to visit.
Texhnolyze features Lux, possibly the bleakest example of this trope.
Tokyo in Tokyo Crazy Paradise, where robbery and murder in broad daylight is considered just a normal day.
Comic Books
Gotham City, mostly since Batman, now. Except the GCPD is full of honest, hard-working people (and Harvey Bullock), and organized crime isn't nearly so big as chaotic, supervillain crime.
Or at least it is now. Year One and The Long Halloween show that organized crime and police corruption were prevalent, and, after The Mafia was taken down, the "freaks" took over.
And its neighbor, Bludhaven, where Batman's former sidekick Nightwing set up shop in his solo book (later to be supplanted by the current Robin and Batgirl in their solo books). Of course, that was before it became a Doomed Hometown....
Hub City in The DCU, from The Question comics, was specifically written to be the most corrupt city in the U.S. Less than ten police officers were considered honest and the firefighters went out armed.
Maranatha, Florida in the titular unfinished web novel Maranatha and the on-going graphic novel series Heathen City, both by Alex Vance.
Madripoor in the Marvel universe is a dystopian, crime-ridden and utterly corrupt version of Singapore. Like the Phillipines!
Mega-City One from 2000 AD's flagship title Judge Dredd certainly qualifies, and the Angeltown district from its Spin-OffThe Simping Detective is depicted as being worse than the city as a whole.
Downlode in Sinister Dexter is a massive city run entirely by gangsters.
Hong Kong, as depicted in many, many movies, is populated by nothing but gangsters, dragon ladies, foreigners looking for a quick buck or an easy lay, and rogue cops.
Cidade de Deus (City of God) as presented in the 2002 film of the same name — it is a part of the Favelas, and thus a case of Truth in Television. Notably, none of the scenes of the film were shot within the City of God itself, because the location was too dangerous to film in.
In Gene Stratton Porter's Freckles, Angel argues that Freckles's parents and relatives did not have to have neglected and abandoned him.
Chicago is a big, wicked city, and grown people could disappear in many ways, and who would there ever be to find to whom their little children belonged?
Tabletop Games
These occur on planetary scales in Warhammer 40,000. The entire Dark Eldar race lives in an extradimensional, planet-sized Vice City, for one, and these are people who quite literally survive by crossing the Moral Event Horizon every day, if not every hour.
In most Cyberpunk games, the background setting is one of these. Night City, in Cyberpunk 2025, is one prime example.
Its schoolyard counterpart Bully is this, BUT FOR THE WHOLE FAMILY!
Paragon City in City of Heroes is a far more idealistic version, with clear lines drawn between good and evil. The upshot of this is, even though there's just as much crime going on, you don't get to partake in any of it. You're a superhero, after all. The Rogue Isles in City of Villains are closer to this, though with their own twists. (For one thing, the "police" will attack you even though you technically work for them.)
Not so much 'work for' as 'are mercifully allowed to live and roam free in case you are the one destined to become strong enough to bring about The End of the World as We Know It'.
Arguably an inversion, as the conflict in the game is based around fighting a totalitarian (though admittedly still corrupt) local government and police force.
New York in the Spider-Man videogames — particularly Spider-Man 2 and Spider-Man 3.
To a lesser extent, Tokyoto from the Jet Set Radio franchise.
Haven City in Jak II, Spargas City in Jak 3 is like this, but much more orderly, considering everyone is armed, and are likely to shoot you if you try anything funny with them.
Santa Destroy in No More Heroes definitely fits this trope, with street thugs in bondage gear armed to the teeth and out for the player's blood, to the point where pretty much no-one actually stays in the city willingly and desperately wants to take the first bus out of town.
In a bizarre example, the little town of Goldshire in World of Warcraft has become a Vice City of sorts, at least on RP servers. It's filled with strippers (13 year olds watching their naked female characters dance), prostitutes (13 year olds cybering), and criminals (13 year olds powergaming.) Goldshire is so well known for this that among the fanbase it is also known as Whoreshire.
It's also filled with a bunch of people who are desperately trying to ignore the aforementioned children. It's a pretty common gathering spot all-around, especially for big groups of friends, as it's obviously rather easy to reach.
The Den in Fallout 2 is referred to as a Wretched Hive, as a blatant Star Wars reference, although it's rather tame compared to New Reno.
Wild ARMs 3 has Little Twister, a Wild West town of outlaws. The various arena towns in the Wild ARMs series may also apply, though they aren't really towns per se.
Zozo in Final Fantasy VI. Everybody's a thief and a liar, and unlike most towns, you'll hit random encounters while exploring.
Condemneddeconstructs this concept by showing how scary such a setting would be. All the crime ridden buildings in Metro City that the main character has to crawl through (and there are a lot of them) are filled with nothing but junkies and crazy homeless people.
True Crime: Streets of LA and New York City took this to a unique level by having the featured cities replicated, or at least with an accurate street and landmark layout. One review for the first game claimed that real life residents of LA could use any shortcuts they know in Real Life in game.
Omega, the unofficial capital of the lawless Terminus Systems in Mass Effect 2 fits in the trope quite well. More subtly all the basic elements of the trope also fit to Illium, an asari colony world where everything is legal as long as there is a contract for it, and criminal organizations and ruthless CE Os struggle for power behind the serene image presented for tourists.
The Godfather: The Game presents NYC this way: You can't go far without running into a business controlled byThe Mafia, Dirty Cops are a dime a dozen, and even staying away from known Mafia fronts doesn't guarantee your safety from running gunfights in the streets.
Pyrite Town. Even for a Lighter and Softer work like Pokemon, Pyrite is a Vice City within a Wretched Hive - it's the only city with police officers in all of Orre, and despite them the hoods freely roam the streets! Let's not forget that this is a city Miror B. ruled over during his days as a Cipher Admin...
In All Points Bulletin, San Paro has some of the things mentioned, minus the prostitution, but it does have drug rings, assassins, and carjackings. As a side note, you have the choice of playing a criminal or a cop.
Adventure Time features the City of Thieves. The name isn't hyperbole - every resident is a thief, and staying in the city for too long causes outsiders to become thieves.
Real Life
Mogadishu, the capital of Somalia. Note that the word "capital" is used loosely here, as Somalia does not have a functioning national government.
Some of the favelas in Rio de Janeiro and Săo Paulo also qualify.
Many areas of Detroit and Los Angeles may qualify.
Many cities become this under weak or nonexistent central authority. Over two-thirds of the world's heroin came through Kabul before the Taliban rolled in. Iraqi cities are the leading suppliers of child prostitutes in the world.
Israel during the reign of Jeroboam II. The prophet Amos blasted it for its corruption, its decadence and its lack of concern for the poor.
New York City until the mid-90s.
Hialeah, Florida also qualifies.
Heroica Ciudad Juárez in Mexico is practically overrun by drug cartels, street gangs, serial killers, rapists and so on. Experiencing an average of eight homicides a day, Juárez has been nicknamed "Murder City" ("Ciudad Asesino"). Some, like Charles Bowden, even allege the police and army are really fighting the cartels—and each other—for control of the drug industry, not to restore order.
Las Vegas during the 1950s came pretty close. The official crime rate was twice the national average in almost every category, and the amount of unreported crime was apparently greater.
Chicago in the 1920s was notorious for rampant corruption, gang activity, and prostitution.
