What's more fun than a carnival? It's got rides and games, frequently travels (though some don't, such as those of Coney Island), and is known for sideshows containing smaller acts than a circus (freaks, contortionists, and cabinets of curiosities). However, in some fiction they're cheap, bad ripoffs. The rides break, the games are rigged against you, and the magic acts are dishonest. The workers are creepy "carnies", too. These aren't places to have fun, they're only there to rip you off, not provide decent entertainment.
Related to Souvenir Land, but distinct in that this isn't asking for you to buy their merchandise. This carnival is too crappy to be a pastiche of Disneyland. Darker versions are Amusement Park of Doom and Circus of Fear.
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Marvel Comics' Circus of Crime plays with this trope - it's a decent carnival, other than the "hypnotizing the audience and stealing their money" part.
In the Young Adult novel Millicent Min: Girl Genius, the title character goes to a traveling fair and thinks it is absolutely disgusting, and being a genius, she figured out that all of the games were ripoffs.
In A Series of Unfortunate Events, the low-quality Caligari carnival has people mocking 'freaks' such as contortionists and ambidextrous people, dangerous rides, fake fortune tellers, and of course, Olaf.
David Foster Wallace, in his Harper's article "Ticket to the Fair" (republished as "Getting Away from Already Being Pretty Much Away from It All" in A Supposedly Fun Thing I'll Never Do Again), is all about the 1993 Illinois State Fair (Wallace, although East Coast educated, was raised in Illinois and happened to be teaching at Illinois State at the time). The experience gives him a serious case of self-consciousness, and he doesn't have much fun at the fair. Not that he finds it completely depressing—there are things that he likes—but overall the fair made him pretty depressed about America.
Anthology Carniepunk. But their carnivals are supernaturally crappy.
Live Action TV
Carnivāle both plays the trope straight and subverts it. The Carnivale itself is full of people who appear dishonest and certainly do their share of bilking the public (rigging games, overcharging for crappy acts, faking "healings"), but they're essentially the good guys who take pride in their way of earning a living. The very few times a ride is unsafe, it's either an honest, tragic mistake (as when Jonesy is drunk and doesn't notice the broken part on the Ferris Wheel) or part of a larger plan (as when Ben, Jonesy, and Samson rig the Ferris Wheel to break so it will trap Justin at the top and Ben can drain his powers).
Craggy Island hosts one of these in an episode of Father Ted. Attractions include "Freak Pointing", an ordinary ladder, a cat spinning on a record player, and of course the Crane of Death, which is a park bench suspended from a crane (so-called because a chap was killed on it the year before).
In an effort to make some badly-needed cash, Al attempts to host one of these to draw in customers to his yard sale during an episode of Married... with Children. Pet the world's friendliest dog! Get advice from a dead parrot!
The 'family fun day' in series two of Phoenix Nights, complete with a questionably shaped bouncy castle, a children's 'play area' (actually a Portaloo full of scaffolding and footballs scavenged from the roof) and face paint which is apparently permanent.
The musical Carnival! (based on the film Lili) is set in one of these. It's not creepy, just done on the cheap.
While Reubans Fayre from The Lost Crown isn't all that bad — at least, not for something with a staff of only six named characters — Nigel remarks to Lucy that hers is the worst "Ghost Train" ride ever. Of course, after a few days' encounters with real ghosts, plastic skeletons aren't likely to impress anyone even if done well.
Some of the parks in RollerCoaster Tycoon start as this, but Ivory Towers takes the cake. It's rides aren't bad (Actually, the Steel Mini Roller Coaster and the Suspended Roller Coaster on this park are very well made), but that's the only good thing. The park is full of litter, puke and it's completely vandalized. This is, obviously, averted at the end of scenario since your job was to fix it and make it famous.
Precocious has the kids putting one on for their school's "Fall Festival" fundraiser, being the way they are they naturally set it up to con the goers out of their money.
In The Fairly OddParents Timmy runs off to become a "carnie" at a horrible carnival that was dangerous with workers that were escaped convictsfairies (Except for the Alligator Man) whose job it is to make kids realize that running away from home is a bad idea.
The carnival from the South Park episode "Cow Days" was so bad that the townspeople called Shenanigans on it at the end.
In SpongeBob SquarePants, Mr. Krabs makes a carnival he calls "Krabby Land" for kids on summer vacation, with the ulterior motive of getting them to buy Krabby Patties. Normally such a thing would be a Souvenir Land, but as he's a huge cheapskate it's made of trash and old stuff found in dumpsters, and the only thing the kids enjoy turns out to be watching Spongebob get himself hurt in the name of amusing them while Mr. Krabs counts his takings.
In the Dennis the Menace (UK) animated series, Dennis visits a fair where all the rides and attractions have been nerfed because of the havoc Dennis and his cronies wreaked the previous year.
The Simpsons episode "Bart Carny" starts with them visiting one of these; eventually they befriend a carny and his son who turn out to be squatters with their eye on the Simpsons' house.
Rocko's Modern Life had an early episode with this trope. It ends with Rocko winning one of the carnival games and the toy he gets breaks about ten seconds later.
In Garfield and Friends, an amusement park called Wonderful World is found to have fallen into disrepair, and is run by Recurring Character Mr. Swindler. The roller coaster has part of the track missing, for instance, and the game where you throw the ball at the bottles? Well, the bottles are only knocked down after being hit by a roller coaster... and even then, they just kind of... fall over. The founder of the park is found under the fun house, and once brought above, is appalled at the state that he's allowed it to get into.
Great Uncle 'Grunkle' Stan of Gravity Falls sets up one by the Mystery Shack in "The Time-Traveler's Pig". Not only are the rides poor, but they're unsafe, as evidenced by the fake inspection certificates he has his niece and nephew put on them (one ride falls apart while Dipper is testing it). And his dunking booth is rigged so that the only thing that can budge the target is a blast from a futuristic rifle.
In the What A Cartoon! Show short "Zoonatiks", the Power Trio are working in one of these at the beginning, called B.T. Hazbeen's Circus. Its low quality is the reason why our heroes want to get into the Hackensack Zoo.
Lapland New Forest, which opened briefly in the United Kingdom in December 2008. Visitors to their website were promised a spectacular Christmas experience, only to find a bare field with a handful of overpriced rides and concessions, a broken ice rink, and entertainers in unconvincing snowman and elf outfits - all after paying theme park prices for tickets. Unsurprisingly, this resulted in numerous credit card chargebacks and a fraud conviction for the park's owners, not to mention Santa and his helpers being beaten up by angry guests. The director is also becoming an example of Never My Fault, blaming the park's failure on crowd manipulation and slanderous media.
It's already been called 'Winter Blunderland' by many newspapers, and got shut down just a DAY after it opened for the first time. It's not only a really poorly set up carnival/attraction, it's also one that lasted less than 24 hours because of how awful it was.