Silent Hill: Bemusement (Doodles)

Protagonist: A pretentious graphics student who was hired by an unscrupulous graphic design firm to create scathing hate art mocking pop-culture entertainment and certain ideologically sensitive aspects of society. Their Silent Hill is very much like abstract art combined with an amusement park, starting out very colorful and vibrant but with the colors beginning to melt and blend together as the game progresses.
Pyramid Head expy: A hulking, twisted mascot suit, like a hideously distorted children's cartoon character crossed with 1960's Ed Roth artwork. Possibly resembling the sharp-dressed Mickey Mouse costumes seen at Disney World, except that the "suit" is actually comprised of diseased, blackened skin.
Nurse expy: A limp, seemingly dead feminine figure in a beautiful, flowing gown imitating a red-carpet celebrity or royal figure, but suspended on strings like a hangman's noose, attached to a floating camera that can hypnotize with its gaze. Once the player gets too close, the figure springs to life and instantly seizes them.

• Walt: All of these guys are named after iconic figures in the history of art, entertainment, and media, starting with the "Pyramid Head" of the game, which is based on mascot suits of course, though I'd be lying if I said that Bewear wasn't an influence too. It's a manifestation of the protagonist's view of their hyper-conservative father, who hated his child's penchant for art when they were younger and was eventually sent to prison for domestic abuse (though it's possible that he may show up in the late-game, and ultimately banish the beast for good by coming to terms with his kid). The face inside the maw originally was just a pair of eyes, but I twisted it into a Picasso-style asymmetrical face to make it a little creepier. This thing doesn't so much as chase the protagonist throughout the game but slowly and silently stalk them, though if it so much as touches them it's an instant kill.
  
• Madonna: The first one inspired by the works shown in Dismaland, this is the Nurse expy from above and also based on the Cinderella/Princess Diana sculpture. It represents how the protagonist feels about fame in general and the kind of attention it attracts, but may also be based off their over-protective mother and how she tried to keep them safe but had to stifle their interests in the process. I made the arms of the "dead" princess long and rubbery so that as soon as the protagonist crosses the camera beam, she can seize him from afar and drag him towards more dangerous enemies.
  
• Muybridge: A huge, fast, and powerful mid-boss that's a ghastly vivisected carousel horse, because it isn't an amusement park without a merry-go-round. I tried to give it a feel more like the canon Silent Hill enemies although the box on its head is a silly jab at the 2013 horsemeat scandal, which Dismaland also referenced with the butcher sculpture in the merry-go-round. It represents all those times when the protagonist sought employment in even menial jobs, only to be overworked, underpaid, and forced to slave away like a beast of burden.
• Pollock: This one's more of an art-themed critter than a cartoon/amusement park one, but since our hero/heroine is an artist I knew I had to include at least one painting-based monster. It's basically the game's Goomba and embodies how art keeps enthralling them no matter how hard they tried to avoid it as a child for their own safety. They look like ordinary Jackson Pollock style paintings and are frequently seen in collections of actual ones, but when you get too close the colors drip off and become blob monsters that attempt to devour them. Maybe they could even take the shape of lost companions later on?
  
• Hitchcock: Based on Dismaland's sculpture of a woman being swarmed by seagulls, representing the way that provocative art and/or people like the protagonist tend to get hounded by publicity, for better or for worse. It's a stationary turret-like enemy that can be seen sitting on benches, ledges, booths, or just on the ground, and if the protag gets near, some of the "birds" attacking it break off and start mobbing them. The closer they are to it, the more birds attack them. Thankfully they can be easily avoided, though the protag may have to brave them to reach certain areas.
• Melville: There's a lot of water areas that can only be crossed by boat or swimming, so of course I had to come up with water enemies, and the first thing I thought of was that orca coming out of a toilet. Since that's supposed to be a jab at SeaWorld and the inhumane living conditions of captive orcas, I imagine it could represent the inhospitable work environments the hero/heroine has had to endure when paying off their tuition fees and how they've been reduced to an object of ridicule by the public. I tried to make it look like the entire front half is divided by the mouth, stopping at the hoop.
  
• Henson: I was originally going to use some kind of bootleg Pikachu in the first draft but that didn't really come out how I wanted, and didn't fit the theme so well either so I discarded it. Instead I came up with this Muppet-like crawling hand monster that embodies the protag's feelings of being paraded around by figures of power and then carelessly discarded. It's alarmingly quick with a nasty bite, and can use its chains like whips, but is thankfully quite frail.
  
• Celine: I know it says Taylor in the drawing, but I think Celine is better and I changed it literally at the last minute. Based on the distorted sculpture of Ariel, this enemy frequently appears in the water areas alongside the Melvilles. It's got a hypnotic voice that compels the protagonist to dive into the water or wreck their boat when they hear it, allowing the whales to nom them. It's based on the "mysterious strangers" that they see just once and never again, as well as how different the public view of people can be compared to their self-image. Their tail and hair colors vary, and as the game progresses they seem to distort more and more...
• Barnum: Another mid-boss, based on this infamous picture of an abandoned clown roller coaster. Every single segment has its own "consciousness", but they all mesh together as a single blended entity, embodying how the protag thinks people simply blindly follow each other and the most popular trends and people, as opposed to rolling with what makes each individual unique and special. It's a bit slower than the Muybridge but also much bigger and longer, able to burrow like a sandworm, and if a middle segment is destroyed the remaining portions become independent entities of their own, Centipede style.
  

There's quite a few other possibilities I could include as well, both based on Dismaland and on other appropriate inspirations such as Bendy and the Ink Machine and Five Nights at Freddy's, but I guess I've rambled long enough.