[[WMG: 50 Blessings has some kind of secret technology in its masks that allows people to see through walls and respawn]]
Naturally, this technology takes a tole on the user's sanity, as the memories of repeatedly dying are inherently traumatic, and Jacket and Biker aren't exactly pinnacles of mental health in the first place. Richter seems to handle it better than most, but even he seems a tad on the sociopathic side. This also means that any character we've seen die (up to and including the Janitors) may return.

[[WMG:The "secret" goal of 50 Blessings / the janitors is false]]

The stuff on the computer, and the stated goals of the janitors, are false. The janitors really are arranging everything as a big social experiment. 50 Blessings uses the "make America strong" pretext as a way to find people who are willing to kill.

Why did the janitors order Rat-Man to attack Jacket? Because they realized that Jacket could seriously have the ability to end the game by destroying the Russian mob, and therefore, ending the whole pretext for the social experiment.

Why are the janitors upset that Biker hacked their computer? They're only acting upset and feeding the Biker lies so that the Biker won't know the truth - perhaps the truth would expose some of the backers of the experiment. When they see that the Biker believes them / doesn't care for politics, they can settle on the "make America strong" explanation as the main one.

The file that the Biker found on the computer was merely one of the [=PDF=]s on the desktop, a brochure that *appeared* to state their goals. It is quite possibly the same brochure that attracted the Biker to sign up for 50 Blessings, but he is such a thrill-seeker that he doesn't even remember reading it before, so when he reads it again, it seems to be new to him.

Why do the janitors more-confidently state their true goals to the Biker if he does *not* hack the computer? Because the secrets of the backers of the experiment are safely guarded within the computer. The janitors can say all they want as long as they don't reveal anything substantial.

(this theory is mainly to allow the maximum possible room for fan-fiction)

* .pdfs only came into existence in 1993.
** Okay, then a Print Shop Deluxe document

[[WMG: The game is part of the Mondo timeline]]

It's always fun to theorize!

Mondo Medicals - a powerful and influential man tries to fight cancer.

Hotline Miami - the man extends his reach into Miami, hoping to develop... let us say... new techniques for battling cancer. Killing cancer on a big scale.

Mondo Agency - The leader of Mondo Medicals successfully took over the country and installed a new president. Unfortunately, the cancer is mutating...

[[WMG: The [[WeSellEverything Man with the Square-Rimmed Glasses]] is the [[PlayerCharacter Hitman's]] [[MissionControl handler from 50 Blessings]]]]

Likewise, he also leaves the phone messages at the start of the level, or has subordinates leave the messages himself. When the Hitman clears each level, he stops at whatever store the Man with the Square-Rimmed Glasses is meeting him at. The food items that are "on the house" are actually money drops, or money mixed in with the actual groceries/fast food/whatever. [[spoiler: the parts where everything begins to get [[MindScrew increasingly weird]] is still part of the Hitman's SanitySlippage, but also represents the Man with the Square-Rimmed Glasses starting to think he isn't up for being part of the program anymore. The part where he is "replaced" with the angry guy refusing to give anything to the Hitman indicates that he is either refusing to pay the Hitman for any more of his jobs, or really was replaced by a far more unsympathetic handler by 50 Blessings]].
* Jossed in ''VideoGame/HotlineMiami2WrongNumber''. [[spoiler:He's a hallucination of a soldier Jacket fought along side with during the war against the Soviets in Hawaii, and [[DeadAllAlong who died when they nuked San Francisco]].]]

[[WMG: The masked men in the hitman's dream sequence represent his conscience.]]

The Rooster is himself, telling him what he already knows.

The owl represents all the people he's killed, hence why he's scared, hostile, and says he's leaving when the conspiracy is taken down.

The horse is a representation of the hitman's girlfriend.

* Definitely some evidence for this. Look at the cover art: the rooster is wearing Jacket's letterman jacket, the owl is wearing a white suit and the horse is wearing a dress.

[[WMG:[[spoiler:Neither the hitman nor the biker died at Phonehom.]]]]
The hitman's survived worse than a knife to the chest, and the biker makes it clear (in his side of the story, at least) that he doesn't want to kill the hitman. He probably gave him a NoHoldsBarredBeatdown, kicked him aside, and left.
* Did he survived worse than a knife on the chest? This guy died from one swing of a police baton.
* Confirmed! [[spoiler:Both Biker and Jacket cameo in events in the 90's storylines in Wrong Number. Biker bears a scar on his cheek, suggesting he lost the fight, but his head being clubbed in was hallucinated]]

[[WMG:The Biker put Richard (or Jacket or Hitman, whatever) in the coma.]]
[[spoiler: From the Biker's perspective, he ends up bashing in Richard's head and telling him that he warned him. The events in Richard's coma could be in no particular continuity (since the dreams are out of whack anyway), and it might be possible that the police and doctors talked about what happened to his girlfriend while he was in bed, possibly able to comprehend what they said. They never did say that he was ''shot'' in the head. Even in Richard's perspective, it looked like Richter shot him in the neck. Inconsistent to how he ended up in a coma.]]

[[WMG: The Hitman is being forced into killing.]]
In the first mission, he vomits at the end of it, a clear sign of remorse. He goes out of his way to save the girl in the second mission. He always seems a little reluctant to leave his apartment (notice how he moves slower than normal). Moreover, we know that the people that are calling him regularly force compliance with threats. Sure, they're empty threats, but Hitman has no way of knowing that. Notably, when he ''stops'' going out based on the answering machine messages, he's much more goal-oriented: revenge against those that tried to kill him. Even the drug-haze can be summed up that way: in order to dull his moral sensibilities, he takes drugs, resulting in the weird style and colors. He doesn't want to kill all these people, but he has no choice: he's been threatened.

[[WMG: The Hitman and the Biker represent the two types of player who play Hotline Miami]]
The Hitman represents players who are interested in the story of the game and want to figure out what's going on. They recognize what they are doing is horrible and wrong, and their primary goal of the game is to stop whoever is doing the killings. They don't include themselves as the cause because they were ordered to do it, so they go after whoever's giving the messages on the phone. They are interested in the characters (Hence the recurring characters of the girlfriend and the shopkeeper) and are hit hardest by their departure. The Hitman's apartment and appearance also implies this: his outfit makes sense for the occasion being both practical and reasonable for the era, and his apartment starts out grotty, becomes decidedly more pleasant as the story establishes a pattern, then seriously goes downhill when the [[WhamEpisode third act happens]], representing the motions of the story.

The Biker represents players who just want to have fun and enjoy the murder. They know they aren't exactly doing morally right things within the game, but they really don't care about that since they enjoy killing and their primary goal is just having fun. They will take the violent route to solving all problems and they only wish to uncover the mystery because that seems to be the only way to end the game and it is seriously dragging on by that point. They know the characters too, but unlike the Hitman they really don't care about them: the women who show up at his apartment are presumably of romantic connection but don't show up again, and the informants he bothers never show up again. Like the Hitman, his outfit and apartment both imply this; his outfit is [[RealMenWearPink pretty absurd and garish]], and probably intentionally so: ever see what an intentionally ridiculous RPG character/Sim looks like? His apartment is similarly stylized: there is a lot more computers and toys then most people could afford in the 80s, but it looks [[RuleOfCool really damn nice.]]

The funny thing is, neither the Biker nor the Hitman get what they want. The Hitman brutally dispatches the Russian Mafiya's bosses without much emotion, never gets the whole picture, and might have even helped the scheme along even when he was trying to rebel. The Biker dispatches the two janitors without much of a satisfying battle as they don't even fight back, and then rides off in his bike to god knows where, not truly being satisfied by what happened. This makes sense, since the achievement for completing the game is "Was that it?", which probably means both types of players coming away unhappy was the intention.

** Jossed, at least somewhat. The Hitman kills because he is indeed forced into it, but [[spoiler: he joined 50 Blessings of his own free will, and wants to murder the Russian mob of his own volition.]]

[[WMG: Everything after "Neighbors" is [[spoiler: the Hitman's DyingDream]]]]
->Zero Context WMG
* Jossed. Jacket's story actually happened, and is canon. [[MindScrew Kind of.]]

[[WMG: There's gonna be a character in a Hippo Mask as a major NPC.]]
After completing the main mission in Chapter 4 - Tension, there's an Easter Egg involving [[http://hotlinemiami.wikia.com/wiki/File:CorneredMask.png a masked man being cornered by Mafiya at the store Jacket goes to]]. The masked man is found dead when Jack leaves the store after talking with Beard. It is quite possible we will actually see and possibly meet this character in the upcoming sequel, most likely as a flashback, since one of the previous 50 Blessings hitman, Jake, is a full-on playable character for it.
* The character is actually wearing the Dennis mask. Unfortunately, they don't appear in the second game.

[[WMG: Manny will get killed by The Fans]]
->Zero Context WMG
* Jossed. [[spoiler: He first meets them when they've been wiped out to a single man by The Son, then ''personally executes Tony for no reason.'']]

[[WMG: [[spoiler:Hotline Miami 3 will center around stopping The General from assassinating the two presidents]] ]]
It seems somewhat odd we'd have such a major development occur completely off-screen, with little build up. [[spoiler: With the slow, sad destruction of the USA centered on the credits that lead up to our Surprise Stinger title page, it seems like we may actually put the violence this series thrives on to use in stopping the death of the world. Perhaps, even better, it'll wrap up the overarching theme of violence's pointlessness with a non-lethal destruction of 50 Blessings?]]

[[WMG: [[spoiler: Biker and Jacket never met]] ]]
Alright, this is a bit of stretch, but I personally believe it makes sense considering the events of Hotline Miami 1, Hotline Miami 2: Wrong Number and promotional art, so just hear me out.

In Hotline Miami, [[spoiler: Jacket fights and kills Biker in his arc. However, in Biker's arc, he kills Jacket.]] As both are alive in Hotline Miami 2: Wrong Number, this doesn't make sense from either perspective. However, it does if you notice [[spoiler: the masks. In Jacket's arc, Biker is fought with whatever mask the player decides to wear, but in Biker's arc Jacket is wearing the rooster (Richard) mask. Now you might belief that the rooster mask was selected for Biker's fight with Jacket because the Richard mask is simply the default mask, but that's never the mask that Jacket is ever really associated with; in the promotional art, Jacket is wearing Aubrey, the pig mask, and in the film representation of his crimes (Midnight Animal) in Hotline Miami 2: Wrong Number he's also portrayed as wearing Aubrey. As Jacket and Biker are just two of the people receiving the phone calls, and since Jake also receives these calls in Hotline Miami 2, it shouldn't be too much a stretch to assume other individuals are involved]]

[[WMG: Biker survived [[spoiler:the nuclear war]]]]
Every other major, playable cast member, including Jacket, was unambiguously [[spoiler:incinerated by atomic fire]] if they weren't killed off earlier. But Biker isn't shown dying in the credits. He's a hermit in the middle of the desert -- not a direct target for [[spoiler:a nuclear warhead]].

[[WMG: [[spoiler: Beard's death was what pushed Jacket into being an assassin.]]]]
[[spoiler: In Hotline Miami 2: Wrong Number, Beard's arc shows that he and Jacket fought in the war over Hawaii together, and after Beard saved Jacket's life from the exploding nuclear plant, their mission in Hawaii was done. After Beard and Jacket were sent back, they evidently stayed good enough friends to remain in contact with each other (and for Beard to feature in Jacket's hallucinations in Hotline Miami.). This could have stemmed from Jacket, being shellshocked from what he'd dealt with in Hawaii, not being able to properly acclimate himself to society, and using Beard, who adapted quite nicely to society after the battle, as a moral crutch. When Beard got killed in the nuclear strike on San Francisco in 1986, this took away one of the few methods Jacket had of coping with his PTSD, which eventually led him to taking up assassination, defaulting back to the violence he grew used to back in Hawaii when presented the opportunity by 50 Blessings.]]

[[WMG: [[spoiler: VideoGame/FarCry3BloodDragon is a sequel to Hotline Miami 2: Wrong Number, set after the nuclear war.]] ]]
Both games have an 80's aesthetic, have protagonists that kill large amounts of people, and [[spoiler: Blood Dragon]]'s description leads credence to this theory: [[spoiler:"Earth has been ravaged by a nuclear war, which erupted in the '90s."]]

[[WMG: Hotline Miami takes place during [[Literature/FearLoathingAndGumboOnTheCampaignTrailSeventyTwo Rumsfeldia]] ]]
Becouse one crapsack timeline isn't enough. I can imagine Hotline Miami taking place during fear loathing and gumbo timeline.