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The protagonist of Cry of Fear, he's a depressed teenager living in Sweden. He wakes up one night in a dark alley, and it all goes downhill from there for him.
- Ate His Gun: This is how Simon offs himself in any of the bad endings, as well as in the closing cutscene of Suicide mode if the players failed to survive until the timer has fully ticked down.
- Beard of Sorrow: Because of the mental trauma and worsened depression brought about by the incident, the real Simon now sports a full beard, indicating that he cared so little about himself that he couldn't be bothered with self-grooming. Averted with Book Simon, who represents his pre-accident self and thus is cleanly-shaven.
- Dark and Troubled Past: Simon was always a depressed individual, as said in the prologue, possibly from a combination of bullying and lack of confidence with his crush Sophie. And then Simon was hit by a car, taking out both of his legs, kick-starting his suicidal depression...
- Decoy Protagonist: You're playing the Book Simon throughout the game, except in the Good Ending. The Real/Sick Simon is the one the story is focused around, while the Book Simon is just a manifestation of his inner demons and suicidal mindset fighting through hell and back to escape, even if it involves killing both of them in the process. The Good Ending turns him into the True Final Boss as the Sick Simon defeats his own inner demons once and for all.
- Disappeared Dad: Although Simon lives with his mother, who will also send him a few text messages throughout the first stretch of the game, there's absolutely no mention of Mr. Henriksson at any point.
- Driven to Suicide: In everything but the fourth and hidden endings.
- Earn Your Happy Ending: As happy as this game can get. In ending 4, Real Simon will accidentally shoot the Police dead, sending him to court. Doctor Purnell will give him something similar to an Insanity Defense, and he'll be sent to a building where he can receive care and regular visits from Sophie and family, and finally come to peace with himself.
- Emo Teen: Bangs covering half of his face, wears hoodie all the time that also also covers his face. Also Simon has been alone half of his life, got heartbroken by his crush, and got hit by a car that made him forever handicapped. Yep! This is our emo!
- Foreign Cuss Word: When on low health, Simon may occasionally exclaim "Aaah... Fan!", which is Swedish for "Aaah... Damn!"
- Half the Man He Used to Be: In a metaphorical sense. Since Simon was paralyzed from the waist down because of the car crash, his lower body is useless and might as well not be there, which caused him immense grief and self-loathing. The Sawer boss can play this lethally straight if he catches up to Simon during his boss fight.
- Handicapped Badass: Simon is paralyzed from the legs down, but that doesn't make his shooting any worse.
- His Own Worst Enemy: In every ending except the hidden one, Sick Simon and Book Simon have a battle to the death.
- In the Hood: Played with. Although Simon wears a hoodie almost constantly throughout the game, he's not doing it to hide his identity.
- I Want My Beloved to Be Happy: In the Golden Ending, Simon finally manages to let go of his feelings for Sophie, who by that point had already been seeing someone else, so she can pursue her own relationship without him holding her back.
- Kill the Ones You Love: In the first, second, or third endings.
- Protagonist Journey to Villain: Played for Drama. Book Simon is basically Real/Sick Simon's attempt to confront his traumas head-on by writing himself in a book as a hero directly confronting his traumas as actual monsters he can kill. Unfortunately, while he gets some temporary respite, the mental pressure it's all putting on him runs the risk of actually making spiral even further into his depression and suicidal tendencies. This comes to a head in the two major choices of the game representing his major conflicts (the Carcass fight/his struggle with his unrequited feelings for Sophie and giving the Doctor the gun/trusting Dr. Purnell to help him) and failing one or both is the catalyst for Simon going off the deep end and choosing to kill himself and take Sophie and/or Purnell with him in the real world, symbolized by Book Simon killing his real self during the final boss fight before going through with it. Even in the Good Ending, Real Simon ultimately has to kill Book Simon, the "protagonist" of the story he's written, in order to move on as he's become just another manifestation and even culmination of his inner demons, covered in blood and as demented-looking as any monster.
- Self-Harm: Whenever he uses a morphine syringe, he pulls down his left sleeve, revealing several scars on his wrist.
- Tragic Hero: Despite his book counterpart defeating Doctor Purnell along with getting out of town and getting safe. Real/Sick Simon still is depressed and upset at how his paralyzed life turned out in all the endings except for ending 4 and the hidden ones.
- Unexpected Gameplay Change: Playing as Real/Sick Simon in the Good Ending is like night and day compared to Book Simon. Sick Simon is confined to a wheelchair and his movement in both mobility and aiming is predictably both sluggish and awkward, and there's no sprint ability.
- Yandere: If the player makes the wrong choices, Simon will become one over the course of the story, killing Sophie in a Murder-Suicide so that nobody can take her away from him.
- Younger Than They Look: Despite the real Simon sporting a full Beard of Sorrow, he's only 19, maybe 20 at best.
Simon's best friend. She kills herself before the fight against Carcass, and is killed for real by Simon in the endings where the player avoided Carcass
- All Love Is Unrequited: Simon has feelings for her, but she doesn't feel the same way.
- Driven to Suicide: Kills herself in the moments before the fight against Carcass. Thankfully, it's really just symbolism of Simon realizing he didn't have a chance with her. However, depending on how Simon chooses to deal with Carcass, the real Sophie is still in danger from Simon himself now.
- If I Can't Have You...: If Simon avoids killing Carcass (thus symbolizing refusing to accept his unrequited feelings and move on), then Sophie becomes the victim of this when Simon decides to kill her to keep her to himself in death.
- Rule of Symbolism: Her suicide represents Simon realizing that he's lost his chance to be with her romantically after his accident and his resulting spiral into depression. How he chooses to handle this realization is decided by how he confronts Carcass immediately afterwards.
Click here to see him without his gas mask.
A strange man in a gas mask and lab coat, he appears at several points in the story. In reality, he is Simon's counselor, trying to help him after his accident by suggesting he concentrate all his personal demons into a book, which results in the massive nightmare Simon goes through over the course of the game. He is killed by Simon in the endings where the player chooses not to hand over a gun he asks for in the asylum.
- Adaptational Villainy: An In-Universe example. From what we see of Purnell, he's a man who gives off incredibly mixed signals. He never answers questions and often leaves after killing someone. That said, he leaves resources, keys, and ammo for Simon in areas when he needs them. In reality, Purnell is a normal psychiatrist doing his best to help Simon with his depression. The version seen with the gas mask represents his lack of trust in the real Purnell.
- Gasmask Longcoat: It's a lab coat, but still.
- Let's Get Dangerous!: In Doctor's Story mode. When advising Simon to write a book backfires horribly, he decides to don a gas mask and arm himself with a revolver to destroy the source of Simon's issues himself.
- Nice Job Breaking It, Hero!: Real Purnell advised Simon to write a book on all of his fears and sorrows, a therapeutic technique, to improve his health. Inadvertently, he made things much worse, and it can end with Simon committing suicide along with killing Sophie and/or Purnell himself. Even in the best-case scenario, things get far worse for Simon before they start getting better.
The protagonist of Team Psyskellar's first game, Afraid of Monsters
, he only appears in the secret joke ending.
- The Cameo: Again, he only appears in the secret joke ending.
- Nice Job Breaking It, Hero!: He's revealed to be the one who had run into Simon and broke his legs.
- The Speechless: Unlike the other characters, his dialogue is displayed entirely in text.
- The Stoner: Is high the entire time he's on screen.
The standard, most common enemy players will encounter. They come in many forms and different clothing and show up everywhere. Their most common method of attacking is to shamble towards Simon and bash him with their hammers. They also come in Crawler forms, who are much faster yet slower in their attacks, as well as variants who are stuck to walls who will block your path until you deal with them.
- Drop the Hammer: Their weapons mostly consist of a carpenter's hammer, and it's not nearly as effective as the tools the other enemies bring.
- Night of the Living Mooks: While not called, or hinted at, their mannerisms, noises, and appearance gives the game this atmosphere sometimes.
- Shout-Out: Some of the Slowers have outfits near identical to Michael Myers, mask and all.
- Unique Enemy: There's a Slower with three heads that can only be found in the TL Trading Company building.
A baby with a swelled up head, their main method of attack is to charge Simon headfirst and impale him with a spike in their head, killing themselves in the process and dealing a large amount of damage for an enemy in the beginning of the game.
- Glass Cannon: Their health pool is rather small, but the damage they can do, especially on harder difficulties, is nothing to scoff at.
- Taking You with Me: They're gonna die when they engage Simon either way, the difference being whether or not they got close enough to hurt him in the process with their head-spike.
- Undead Child
- Your Head Asplode: Their only attack involves a spike shooting out of their spine and through their head, causing this.
Decomposed children who could very well be the victims of the pedophile in the apartment building, they rush Simon with their fast speed and slash at him with their dual knives. They're wrapped in trash bags, and will burst out from them if Simon is detected.
These monsters look like housewives, down to the hairstyle and blue dress. Their limbs have been replaced by bloodied metallic spikes that they use to jab and rush Simon with. They are fast, can deal large amounts of damage quickly, and so very, very loud while doing both of those. These enemies only appear in the Apartment segment regularly, and get more and more diluted as the game progresses.
- Driven to Suicide: Like many other enemies who kill themselves in some fashion, the Faster will stab herself in the eyes when her health is depleted.
- Eye Scream: Upon being defeated, they'll stab themselves in the eyes with their limbs before falling over.
- Hell Is That Noise: Their spiked limbs create metallic tapping sounds as they move. This is especially in place when you decide to flee from one and you can still hear them running. Not to mention the screaming they do for everything; detecting you, attacking you, and even while dying.
- Jump Scare: The game makes sure that the most common way you'll encounter these shrieking enemies is when you open a door to a new area or when you turn the corner with one in your face.
- Lightning Bruiser: They're quite hardy for something in the beginning of the game, and can quickly and dangerously throw a violent hit.
- No-Sell: Shots fired at their metallic arms and legs will bounce off harmlessly and don't deal any damage, and the male variant encountered in the co-op and Doctor campaign can laugh off headshots due to the steel cages around their heads.
- Spear Counterpart: It's possible to encounter a male variant in the Doctor's Story or the co-op campaign, which also has the unique trait of having metal bars growing out of its shoulders and protecting its head from headshots.
One of the few ranged enemies in the game, as well as the only other enemy capable of flight, the Flygare is a decomposed man tied to a bed facing down that floats in the air. They bring two methods of attacking; a blood spit when Simon is away and a pair of scissors for when Simon approaches.
- Airborne Mook: The only common enemy that stays in the air, up until they're defeated and they plummet from the air.
- Glass Cannon: Their health isn't too good, but their blood spit is extremely lethal on higher difficulties.
- Long-Range Fighter: Their most common attack is their blood spit, though they still bring two scissors in case Simon is the appropriate distance for it.
- Non-Standard Character Design: A humanoid figure strapped to a bed, squirming and thrashing while trying to escape? Pretty unnerving, and quite uncommon. Also bears a striking resemblance to some monsters from Silent Hill 2.
A large mass of flesh that stays mostly immobile, they serve as obstacles rather than enemies to Simon. Approaching them triggers an animation of Simon getting impaled, and then dragged to the unseen bottom of the creature, presumably to get added to the mass. In order to progress, another path will need to be taken. In Co-op, a variant appears while on the boardwalk. These Flowers can actually be damaged and killed, have only one appendage that can instantly down (not kill) a cop, and rise out of the water rather than block your path.
- The Assimilator: Plans of having them slowly move around, impaling Slowers as they pass by to add to the mass were cut, but their kill animation on Simon remains, and they heavily imply this by way of dragging his body into the hole they emerged from.
- Body of Bodies: While you can hardly see any distinct body parts other than the faces and the sharp appendages, they are composed entirely out of the flesh of anything they catch.
- "Instant Death" Radius: The moment you enter its vicinity, it will kill you instantly.
These monsters are built around catching Simon off guard. Their territory is down below where the sewers are, where they lay back and quickly rise up from the water when Simon approaches too close. Their bodies are wrapped in barbed wire, making their arms useless and leaving them to whip Simon with their long tongues. That is, until you damage their chest enough to free their arms, which they'll then use to whack Simon with.
- Jump Scare: Without the screaming nature of the other enemies, but they tend to show up in the sewers where everything is dark and ambient. Every single one is built to do this.
- Punny Name: Of a sort. They're larger in the belly than the other monsters, like a sumo, and they are only encountered in the sewers. A Sewmo. It could also be a shortening of Sewer Monster, where they make their sole appearance.
To say these monsters are tall is an understatement. Everything about them is massive — their height, size, steps, and most importantly; their damage. Capable of wiping out half of Simon's health in one swipe, they serve more as obstacles to avoid rather than enemies to fight
. They move slowly, but they take large strides. The game places heavy emphasis on running past them to advance rather than trying to kill one. You have nothing to worry about if you're concerned about space, because the game's merciful enough to only place them in large open areas.
Keeping up with the theme of suicide and depression, the Suicider is the one of the only other enemies that uses ranged methods of damage. They bring a Glock pistol, the basic handgun of the game, and come in groups. Sounds deadly, right? Thankfully, they are very poor at self-preservation and will sprint at Simon full speed while firing their shots wildly, ruining their aim. Should Simon get too close to one or dodge their shots long enough, they'll use the last bullet to shoot themselves and drop their weapon. This is a great way to obtain the ammunition for your most versatile weapon. They only appear in two segments; when Simon is on Saxon Avenue and in the Insane Asylum.
- A-Team Firing: Their preferred tactic when it comes to damaging you.
- Boom, Headshot!: They have rather big, swollen heads. So if you feel like trying your aim, you can headshot them rather than wait for them to shoot themselves.
- Driven to Suicide: Two of the three methods to get rid of them.
- Exactly What It Says on the Tin: It blows its brains out if you get too close.
- Metal Slime: They show up a fixed number of times (that is, only twice in regularity), are easy to defeat, and will drop one mag for the Glock no matter how they die.
The Faceless is a completely naked, bloodied, and featureless monster that tend to come in groups. Rather than slowly shambling or floating like the rest of the monsters, they're very twitchy and will quickly close the distance. They first appear en masse in the school segment after the power is turned off. After this, they'll appear less often but are still present, especially when reaching the Insane Asylum.
- The Blank: Despite their name, this is actually an Averted Trope. They all have mouths, and some have eyes.
- Blood-Splattered Warrior: Drenched in blood, and are absolutely relentless with their attacks.
- Fragile Speedster: They're quick compared to everything else, though can't quite take a hit.
- Full-Frontal Assault: Is completely naked.
- Screaming Warrior: Another enemy with a tendency to yell and roar at you while they attack. The first time you encounter one, that scream is all the warning you get because it spawns right next to you and tries to beat you to death.
- Zerg Rush: The college is swarmed with these things.
The Stranger, nicknamed Facebook for an obvious reason, is a strange monster. The Stranger's a man in a fine suit, but with an open book for a head. Rather than the straight-forwardness of the other enemies, The Stranger will stay out of sight and telepathically torture Simon until he's dead
, rather than try to confront and beat him up. The Strangers could possibly be the same entity, as you'll rarely encounter him except in set areas, and rather than dropping dead, he'll spasm out of existence when defeated. Overall, it'd be best if you avoid even confronting this enemy.
- Hell Is That Noise: One of the ways to tell if he's around, as he breathes heavily when nearby.
- Non-Standard Character Design: The Stranger, in comparison to everything else encountered, is a man in a mostly clean suit, normal hands, and has little animation until he's killed, rather than the mortified monsters everything else is. Given that Simon's Book is a sentient being, it's likely he's a manifestation of its influence, and thus not part of Simon's mind like all the other enemies.
- Psychic Powers: His method of attacking is this, with how quickly it'll hurt you varies on difficulty.
- Rule of Symbolism: The fact his head is a book represents that Simon's book therapy is only making his mental state worse.
These ghostly white women are another telepathic attacker, though their effects are much more instantaneous, yet they can be canceled out. When encountered, if Simon is holding a firearm, they'll use their influence to force Simon to shoot himself in the head, unless Simon breaks out of it. Those who think that this means the best method is to rush them down and beat them with melee weapons will be surprised to know about their hidden attack; a baby will burst out of their wombs holding two knives to attack Simon with in quick succession.
- Chest Burster: How a baby will make its entrance should you get too close to mom.
- Fetus Terrible: The baby might not be fully developed, but it's far down enough to burst out and stab Simon when needed.
- Undead Child: In the case of the baby.
- Psychic Powers: In this case, it's to force Simon to shoot himself in the head. Also seems to be what's making them float slowly towards Simon.
These bloodied women make their only appearance when Simon is in the Subway maintenance tunnels. While not entirely unique in terms of combat, bringing only a knife, they're quite common in the tunnels and Simon can find himself getting attacked by multiple Citalopram at once.
- Hell Is That Noise: In the dark tunnels where a flare is your only light source, their rapid, heavy breathing can quickly cause some panic, as it's the indication that they're about to charge and attack from the shadows.
- Meaningful Name: Their name, Citalopram, is a type of drug that can treat depression, a main theme in the game. They also have harsh, jagged breathing, a potential side effect of Citalopram.
- Rule of Symbolism: Being named after an antidepressant, having side effects associated with said antidepressant, and being in a game riddled with suicide and depression themes, it's not too difficult to guess that Citalopram was the medication that Purnell prescribed to Simon.
- Zerg Rush: The Subway in single-player is just riddled with these women who'll rush Simon in large groups. In Co-op, a certain staircase will collapse and drop a Cop in a room with a literal dozen of them surrounding him.
These ghostly white women bear a noticeable semblance to the Drowned, but unlike their telepathic counterpart they prefer to close the distance and stab Simon with their knives. Appearing in the woods segment, normally they wouldn't be much of a threat to Simon, but with Simon reduced to only having a tree branch as a weapon and lamp providing little illumination they're a force to be reckoned with in the dark.
- Fragile Speedster: They don't have much health (for reference, Simon can kill one with two swings of a tree branch on the lower difficulties), but they can attack swiftly and rack up damage, especially if several get aggroed at once.
- Hell Is That Noise: They don't go full Screaming Warrior on you, but when they spot you they can be detected by their rapid, panicked breathing.
- Knife Nut: They come packing a knife they're all too eager to use on you.
- Zerg Rush: The forest in single-player is just riddled with these women who'll rush Simon in large groups if aggroed. Even worse, since on a first playthrough without unlocks Simon is only armed with a tree branch post Bag of Spilling moment and the lack of morphine available (and what ones there are are usually past a group of these women), this can very easily kill Simon.
The embodiment of jumpscares and appearing in the woods segment, the Hanger (not to be confused with the Hangman) is similar to the Drowned in appearance, but instead of telepathically attacking Simon or stabbing him, these women will drop from the trees while on a noose while screaming and damaging Simon on the way down.
- Driven to Suicide: Another enemy that commits suicide, and it'll hurt you too whether you're careful or not.
- Jump Scare: Their only method of attack, and what also kills them. You'll need to cross an entire forest filled with them, so have fun.
- Screaming Warrior: Shrieking on the way down to give you a heart attack in the ambient woods. The scream is the only warning you'll get to move out of the way, but you'll only have half a second to react before they drop.
The Upper is a rare enemy, only appearing twice. It's essentially a Slower that's doing a handstand and attacks by kicking with its limp legs, but does the same damage as the Slowers. Their most defining feature is not their combat or even appearance, though. It's their terrifyingly loud and drawn out roar when they find you.
- Abnormal Limb Rotation Range: Part of what makes them so unsettling to look at is that Uppers seem to move like all of the joints in their bodies are horribly broken, with their legs that they use to kick at Simon swiveling at highly unnatural angles. This is because while their models are separate, they still use the same animation rigs as Slowers, so when an Upper swings its leg to hit you, it's actually a Slower waving its arm to smack Simon with its hammer.
- Dynamic Entry: Every time you encounter them, something was broken both in singleplayer and co-op. A door was shattered by one in single-player as you get near it. A bathroom collapses in co-op and drops one of the Cops in a room with two of them.
- Foreshadowing: The Upper has legs that are contorted and bent in all the wrong ways. Simon's legs no longer work due to a car accident.
- Hell Is That Noise: Holy shit, that scream. It only happens once in the entire campaign, but it likely will be scarred into your memory for a long time.
- Jump Scare: This seems to be their sole purpose. Uppers are incredibly rare, appearing only once throughout the main story, and once more in pairs in the co-op campaign. Both of these times, they will burst out from behind something when the player least expect them and charge at full tilt, all the while letting out their insanely loud screams that will send you running in panic.
- Moveset Clone: Of the Slowers, as they are literally just reskinned versions of those enemies, and use the same animation sets despite their different body arrangement, which adds to their scare factor.
- Rule of Symbolism: The Upper has legs that are broken and disjointed. Likely to represent Simon's legs being irreparably damaged.
- Schmuck Bait: That aforementioned bathroom? It has an Assault Rifle sitting on the toilet just waiting for a certain Cop to pick it up. And then the door locks itself and the floor begins to crack...
- Sensory Abuse: Their scream is so loud that it becomes ear-piercing.
- Unique Enemy: There is a single Upper throughout the entirety of the main campaign, only appearing out of the blue as a Jump Scare when Simon is traversing the surreal underground maze with the slamming doors, just before reaching the asylum.
One of the last enemies encountered near the end of the game, they wear metal, beaked masks that cover their entire head. Similar to the Faster, they are quick, can deal plenty of damage, and also loud about it. They wield a fire ax and will sprint towards Simon relentlessly until one of them is dead. They're only found in the Insane Asylum, with plenty of hallways and sharp corners to compliment them.
- An Axe to Grind: They use a fire ax to attack you.
- Blood-Splattered Warrior: Their sweaters and masks are covered in blood.
- Jump Scare: Like the Faster, you'll likely encounter them as soon as you turn a corner or enter a new area. They'll also be screaming all the while.
- Lightning Bruiser: They can take a beating, and can return the favor right back to Simon while sprinting at top speed. They really are a test of your skills, since the Asylum only has so many magazines for your guns and a mediocre melee weapon.
- Plague Doctor: Their metal masks are evocative of this.
- Screaming Warrior: It shouldn't surprise anyone that there's another demonic entity that screams bloody murder while hurting you at this point in the game.
A unique enemy only encountered in the Co-Op Campaign and Suicide Maps. It's a combination of The Sawrunner and the Crazyrunner, being a long-haired monster that dual-wields chainsaws in a frenzy to kill anything in its path.
Not to be confused with the more iconic Sawrunner, Sawer's the boss battle for the Apartment building. A very tall, lanky, and nail-covered naked man wielding a chainsaw, he's capable of splitting Simon in half in one swing. He moves slowly, but will take long strides to keep up in the small room you'll do battle in.
- All Just a Dream: Somewhat implied, since he only shows up during a Nightmare Sequence that Simon has.
- Chainsaw Good: Like a few other enemies in the game, he wields one. Also like other enemies in the game, it's capable of killing a player with one hit.
- Damage-Sponge Boss: Sawer is immune to damage, though if he's hit enough, he will kneel down to rest. The eye on his back will open, allowing you to damage it directly. Though at this point in the game, your weapons (a basic handgun and a pocket knife) won't be spectacular enough to defeat him in one round.
- Driven to Suicide: A reoccurring theme for many enemies and the game itself, Sawer will decapitate himself when he's defeated.
- Eye Scream: Shooting Sawer will do nothing to his health, but it will stun him. Once he's stunned, a massive eye will open on his back. This is only way to kill him.
- Foreshadowing: In Sawer's kill animation, he literally removes Simon's legs, rather fitting since the real Simon's paralysis below the waist is one of the major catalysts of his suicidal depression.
- Full-Frontal Assault: Is completely naked, though lacks the genitals.
- One-Hit Kill: Getting caught in his Chainsaw's swing will trigger an animation of Simon being sawed in half with no chance of survival.
The boss battle for after Simon has cornered The Doctor, Mace has swallowed the only key after The Doctor locked Simon in a closed room with him. True to his name, he brings an actual spiked mace to hit Simon with. Like Sawer, he's impervious to damage, but fortunately the room is flooded with water, and there are faulty electrical generators to tamper with...
- The Brute: The biggest, most physically powerful boss Simon faces. He can't even be killed with bullets.
- Carry a Big Stick: One he's named after, of all things.
- Exactly What It Says on the Tin: He's called Mace, and he wields a giant fuck-off mace.
- Extreme Omnivore: He swallows a key with no effort before starting the fight.
- Fat Bastard: A truly large opponent you'll be dealing with.
- One-Hit Kill: The Mace is as lethal as it looks.
- Puzzle Boss: Unlike Sawer, he won't succumb to pain and take a moment to rest to expose his weak point (though he will stop to sniff the air if you evade him long enough). Instead, players will need to maneuver around him and reach the correct power box to activate and electrify the water he's in. It'd be wise if you get out of the water before this takes effect, by the way.
A horrifying chainsaw-wielding monster that relentlessly pursues Simon throughout the game, from an alleyway all the way to a sewer in the forest. He even chases the police in Co-op Mode, and is also the final boss
- Ax-Crazy: Substitute an axe for an instant-kill chainsaw.
- Chainsaw Good: True to his name, he's a screaming, chainsaw-wielding abomination.
- The Determinator: He's the only boss that never gives up, even if you kill him.
- Malevolent Masked Man: His signature headwear consists of three smiling theatrical masks.
- Nigh-Invulnerability: Contrary to popular belief shortly after the mod's debut, Sawrunner actually is killable, though he takes an absurd amount of damage to bring down and he will respawn to chase you again in his next encounter anyway. You'll only have a chance of bringing him down using high-end weaponry unlocked through repeated playthroughs.
- Potentially subverted in the non-canonical Co-op Mode, where the cops have to work together to bring him down in their final encounter with him.
- Recognizable by Sound: Any time you hear a chainsaw revving up, you'd best start running. Or his own music track, "Sawrunner", which plays in every one of his encounters.
- Signature Roar: Ooooooooorrrrrrrh aaaaaaaaaaaaargggggggghh!
The Carcass is an odd-looking boss enemy. What might as well be a slab of meat on a chair floating in the air, this monster is possibly what had Sophie jump off the building when Simon is with her
. Unlike previous battles, this monster is capable of taking damage through direct means and requires no gimmicks other than a sense of dodging and precision. Carcass will fight entirely with ranged attacks that track Simon as he moves.
- Damage-Sponge Boss: Should you decide to fight him. The game gives you some ammunition thrown around, but for the most part you'd better ration your shots before encountering him.
- Disney Death: When defeated, Carcass will plummet several stories, then vanish.
- Long-Range Fighter: Only attacks with ranged methods, and only you can do the same.
- Rule of Symbolism: He's bound to a chair, just like Simon.
- Skippable Boss: He's the only optional boss in the game, but whether you decide to spare Carcass or not affects the game's ending.
- That One Boss: Carcass can be regarded as one of the toughest fights in the game. There is an option to avoid this fight, but doing so will have Simon in the real world murder Sophie in suicidal anger.
This is another nightmare entity that Simon encounters in a maze near the end of the Subway Tunnels. Completely invulnerable and wearing a duct taped straight jacket, they're hanging upside down on a hook. Its tentacle shaped head will instantly kill Simon. With these two ideas combined, it's clear that Simon needs to run away from the Hangman while trying to escape from the maze. Fortunately, the Hangman is suspended on a hook on a slow moving track and has no free will over where it'll go. Better hope you don't turn the corner while he's coming towards the same hall.
- Advancing Boss of Doom: Acts more like a mobile hazard than a boss, but still in effect. Also invoked in the victory cutscene, where Simon scrambles to shut the door mere moments before it reaches him.
- One-Hit Kill: How it happens is unknown. But you wouldn't want to stick around and see how anyways.
The man who you've been trailing behind the whole game, you finally confront him near the end of the Insane Asylum. Before the battle, he requests that you give him a new, better gun to replace his revolver. When you retrieve it, you have the option to give it to him or deny him the gun. Not giving the gun will have him admit that he's disappointed that you don't trust him, before shooting you to cut your health bar down permanently. Giving him the gun will have him thank you for trusting him, before shooting you with the gun you gave him for a bigger penalty to your health. Afterwards, you'll encounter him in the attic for one last shootout. Not trusting him will have real Simon murder the real Purnell, blaming him for all of his problems and accusing him of not helping him before killing himself.
- Big "NO!": The victory cutscene has him lay on the floor wounded, before Simon approaches him to stomp his head in. He yells one out before he's dead.
- Disc-One Final Boss: Killing him leaves, depending on your choices, either Book Simon or Sick Simon to fight as the True Final Boss.
- Flunky Boss: Not on purpose, but every now and then some Suiciders will appear from the right to attack you. Naturally, due to their shoddy aiming skills, they serve better as a source of extra ammo than actual threats.
- The Heavy: To Simon, whom believes he is causing the monsters to appear.
- Jerkass: Unlike the real Purnell.
- Mad Doctor: Believed to be this, in any case, and ironic considering his dialogue seems to indicate he sees himself as the only actual sane one. At one point, Simon runs into him decapitating someone who isn't a screaming monster.
- One-Hit Kill: Trying to act bold and rushing into his half of the attic will trigger an animation of Simon getting headshot by him. It's best to just use cover the same as he does.
- Rule of Symbolism: The fight with him can symbolize one of two things, depending on your choice of what you do with the gun beforehand.
- If you do not give him the gun, he will shoot you with his revolver and cut your health permanently by roughly a quarter, which is less than he cuts if you give him the gun. Killing the doctor in this scenario represents Simon fully giving up on Purnell's methods of trying to help him with his depression, and since he never opened up to the doctor's methods, he wasn't hurt as bad when it didn't help much, hence the lower health lost.
- If you give him the gun, he will do the same as before, except it will cut your health by a third. Killing the doctor here represents Simon opening up and trusting Purnell, therefore killing his warped vision of him. On the other hand, the greater loss of health symbolizes that Simon felt even worse when the book didn't help much, as he had gotten his hopes up.
- Suspicious Videogame Generosity: All that ammo and syringes lined up nicely on a table in the attic? You bet this is the last showdown.
- Whack-a-Monster: Whack a doctor actually, as he's only vulnerable when he pops out of cover to shoot at you or changing cover.
Good Ending Boss
The final boss should you decide to fight and defeat Carcass, and trust The Doctor with the gun. This is the Dark and Troubled Past
Simon, the one you've played as, with the wounds he's accumulated during this whole ordeal. You fight him as the Sick Simon (the depiction of the real world Simon) while on a wheelchair. He will charge towards you on four separate occasions, each deadlier than the last, retreating each time when warded off before finally dying. The first confrontation will have Book Simon armed with a Glock pistol. The second encounter will have him use a shotgun, the third time he'll be using a machine gun, and then he'll finally use a sledgehammer and a flare to charge you. He'll also appear in Co-op mode as a random encounter, where the map will go black and white, his theme song will play, and he'll be lurking somewhere, forcing the Cops to deal with him.
- Battle in the Center of the Mind: What this fight seems to be, with the real, handicapped, and normal-looking Simon battling with his depressed and dark self.
- Blood-Splattered Warrior: He will be covered in blood from what he's experienced, including the blood from the gunshot that The Doctor inflicted and the gunshot in his head, that real Simon will attempt to do, looking no different than many of the monsters you've killed to get this far.
- Drop the Hammer: The final confrontation will have him bring a sledgehammer, one of the game's strongest melee weapons. He'll also charge at you from the shadows with it.
- FaceMonster Turn: He's the form you've been playing as for the whole game, and now in order to save Simon from suicide you need to kill him as he's become no different than the other monsters you've been fighting off all this time.
- "Get Back Here!" Boss: Each time you deal enough damage to him in story mode, he'll retreat, forcing you to slowly pursue him in your wheelchair.
- He Who Fights Monsters: Simon made him to confront his traumas as realized as physical monsters. By the end, he's become just another monster and the biggest one of all Simon himself needs to kill.
- Mighty Glacier: In Co-op mode, he'll slowly move along, blasting the Cops with a shotgun and taking massive damage. In the main game, though, he's more of a Lightning Bruiser.
- More Dakka: The third occasion will have him bring an assault rifle, which is very good at shredding your health if you're not quick enough.
- Shotguns Are Just Better: One of the weapons that Book Simon will bring. In Co-op, this is the only weapon that he will use, and you really don't want to be on the business end of it.
- Slasher Smile: Seems to be sporting one under his hood and past all the blood. In the co-op modes, he will have a very, very prominent one, with his mouth opening waaaaaayyy too much.
- This Is Gonna Suck: When the screen goes black and white in Co-op and the theme song starts to play. Expect an Oh, Crap! or several from your buddies. Conveniently, this theme song has the alternate name called 'fucked'.
- He can also appear to ruin your night when the Cops are in the Insane Asylum/Forest, where they're mostly unarmed and helpless with tree branches.
- Unusable Enemy Equipment: In the battle preceding Ending 4, Book Simon will wield the MP9 against you around the middle portion of the boss fight, which can play this straight if you're not one of the few who have donated money to Team Psykskallar while the game was in development.
Bad Ending Boss
The final boss in the bad endings where Simon avoids Carcass and/or doesn't trust The Doctor with the gun. This is the incarnation of the real, wheelchair-bound Simon. This battle is a close quarters dodging game, where Simon will sit behind metal bars where Book Simon cannot hurt him while using psychic powers to fling items at him. Eventually, though, the bars will release, allowing Book Simon to brutally attack Sick Simon.
- Battle in the Center of the Mind: What this fight also seems to be, the depressed and dark incarnation of Simon does battle against the real incarnation of Simon. Winning this fight will have the real world Simon commit suicide, after murdering Sophie and/or Doctor Purnell.
- Beard of Sorrow: Seems to have grown a thick stubble, like the real Simon.
- Driven to Suicide: The fate of the real Simon when you 'win'.
- Flunky Boss: One that uses Mooks as part of the puzzle. Unique Faceless will appear with their own textures. One of them has a valve replacing their head, which is needed to progress.
- Handicapped Badass: Although he's helpless when you reach him, he puts up quite the resistance in the meantime.
- No-Holds-Barred Beatdown: The ending to this battle will have Book Simon knock Sick Simon off the wheelchair and mercilessly attack him while he's down. This is symbolic to Simon's horrible depression finally overtaking him, making him commit suicide.
- Psychic Powers: He'll be using this to hurl objects towards you. And they do low damage individually, but can quickly stack up with how much is being thrown towards you.
- Puzzle Boss: Sick Simon is sitting behind invulnerable bars, and will launch objects that Book Simon will need to duck under and jump over to avoid damage. After that, several unique Faceless enemies will appear from the sides with a valve for a head, which can be used to open the bars. You'll do this four times until you're free to pummel Sick Simon.
- Taking You with Me: When you finally reach Sick Simon, Book Simon will knock him off his wheelchair and beat him up before strangling him to death, which will make him collapse as well. Observant players will notice that you're actually losing health while strangling Sick Simon before you collapse.