Over the course of the first game, he dons various animal masks (leading to other fan nicknames) and performs a number of brutal assassinations in response to cryptic messages left on his answering machine.
The game opens with a Tutorial sequence with Jacket in a pig mask being trained by a Bum. He kills three unarmed Russian Mafia enemies when the surreal setting changes to a dimly lit bathroom. Jacket exits and is confronted by a living room featuring a coffee table with a vinyl record player on it, and three comfy chairs each with their own lighting and animal-masked occupant.
The blue-lit woman in a horse mask, Don Juan, cordially greets Jacket, realizes he doesn't know who she is, and comments that maybe he should leave it that way as he's done some terrible things. The red-lit man in mobster garb and a piercing glare owl mask, Rasmus, says he doesn't know Jacket and treats him with hostility. The sickly-yellow lit man in Jacket's clothes and a rooster mask, Richard, tells Jacket that he knows him, and that they met on April 3rd (the date of both Jacket's first masked job, and of San Francisco). Richard sees that Jacket is starting to remember his life, and the setting becomes Jacket's apartment.
Jacket wakes up on April 3rd in his dirty and notably two-bed apartment. He receives a call from "Tim's Bakery" telling him a package of ingredients has been sent to him. The package contains the Richard rooster mask and instructions to pick up a package at a metro and deliver it to a dumpster at "point F-32." Jacket dons the mask and does so, killing several Russian mafia enforcers on the scene, but at F-32 he is confronted by the tutorial bum, who attacks him for interfering with the dumpster and is promptly killed. This provokes Jacket to vomit at the scene.
Jacket drives to a local convenience store where Beard is the cashier. Beard greets him and says he hasn't seen him in a long time and was worried about him. He comments that the last time they talked Jacket told him about his girlfriend dumping him. He quickly switches the topic and gives Jacket a midnight snack "on the house".
On April 8th, Jacket's kitchen table features several 50 Blessings newsletters from a patriotic organization he's subscribed to. He gets a call from "Linda" to discipline naughty kids. He arrives at the given address to find it's a Russian mobster hangout and kills them. He proceeds to a local pizzeria, where Beard is the cashier. Beard gives Jacket his desired pizza before Jacket orders, telling him it's "on the house."
On April 13th, Jacket's apartment contains several newspaper clippings of his April 8th job as mementos or trophies. "Thomas" at the methadone clinic leaves him a message to swing on by. Jacket again arrives to find a den of Russian mobsters, this time seeing the tied up corpse of a walrus-masked killer, Earl. He visits a local VHS store, where Beard is the cashier. He raves about the recent killings, saying that a bunch of "Ruskies" is no loss if you ask him, and that it all sounds like a cool slasher flick. He gives Jacket a movie, again "on the house." He encourages Jacket to enjoy himself.
On April 25th, Jacket's apartment is cluttered with empty pizza boxes and more news clippings. Hotline Miami's dating service worker "Kate" tells Jacket they've set up a date for him. He arrives at the address to find it's an expensive villa guarded by several Russian mobsters and many security cameras. After dispatching them, the owner, a movie producer wearing a bullet proof vest, attacks Jacket, who retaliates by gouging his eyes out. In the media room Jacket finds a drugged Girl surrounded by cameras who begs him to kill her (or if it's done so by the player, Jacket starts to leave and the girl yells at him from the room, calling him an "asshole" and harshly encourages him to "finish the job." the player cannot leave until he goes to the girl). He instead takes her to his car. Jacket heads to a bar, where Beard comments that he looks sick. He makes him a custom drink for free.
Jacket returns to the dirtied animal living room, now noticeably more littered with broken things. Don Juan comments that Jacket's been busy. She says that a picture is starting to form and that she doesn't like the way it looks; Rasmus berates Jacket's return and says he's not a nice person and that he makes him sick; Richard comments that Jacket still doesn't understand his connection to Richard and asks four questions:
On May 5th, Jacket's apartment has more newspaper clippings revealing that he was recorded in the movie producer's villa. The Girl is on his couch next to a vomit bucket. "Blake" from an electrician service calls about fixing a power outage. Jacket arrives to find a large mafia hangout, where he finds and detonates the body of another masked killer, this one in a tiger mask which is presumably damaged and bloodied by the explosion. He visits Beard's convenience store, the inside of which is empty, and the outside of which features a group of Russian mobsters beating a wolf-masked killer to death. Beard comments that the streets are no longer safe and that he was worried about Jacket. He again gives him a snack for free because Jacket's his friend and his money's "no good here."
On May 11th, Jacket's newspaper clippings and empty pizza boxes have been moved out of the living room and into the kitchen (away from where Girlfriend sleeps), as has the vomit bucket. Girlfriend is in the bathroom, looking in the mirror. "Dave" from pest control sends Jacket to a large house full of Russian mobsters. After killing them, Jacket inspects a nearby manhole cover and finds the mutilated dying body of a alligator-masked killer, Jones. Jones tells him that he finally understands that it's all a dream and dies. Jacket visits Beard's pizzeria, and Beard comments that Jacket looks worried and that business has dried up, saying "maybe they've lost their taste for pizza... maybe it's time to close up shop after all." As always, Beard gives him his order for free.
On May 13th, The Girl is taking a bath, and pizza crumbs are present on her sheets on the couch. Jacket has further tidied up, moving all his newspaper clippings save the most recent onto the spare bed. "Don" from the Hotel Blue calls Jacket to come in as a back up receptionist, because their other one "went home due to stomach problems" (Biker instead uses May 13th to investigate the phone calls). On his way downstairs he meets a suspicious Janitor (Dennis) but continues to his car. The Hotel Blue is full of armed waiters, Russian mafia guards, and mafia-affiliated pro-Russian politicians connected to the Russo-American Coalition, all of which Jacket kills, but he spares yet another suspicious Janitor monitoring the job (Jonatan).
Jacket visits Beard's customer-less VHS store, where Beard excitedly asks him if he's following the news of the killings, and says that a friend of his in the police force told him about a rumor that there's a full group of masked killers. Beard comments that it fascinates him, like something from a movie. He tells Jacket to take whatever he wants on the house, because "that's what friends are for."
On May 23rd, all kitchen clutter and clippings has been either thrown away or moved onto Jacket's spare bed. The Girl sits upright on her couch. "Harry" from condo management tells Jacket about a huge mess he needs to clean up. He arrives at a series of several Russian occupied condos, which he quickly clears out. Before returning to his car, the phone of the top level condo rings, informing Jacket that a prank caller needs to be dealt with at the phone company, Phone Hom.
Jacket arrives at Phone Hom headquarters to find a motorcycle parked outside and all the employees inside dead. In the manager's office he confronts a Biker hacking the manager's computer, who tells him he's "dead meat" and attacks him with a meat cleaver. After a long fight and multiple hits with a golf club Jacket apparently defeats Biker, seemingly destroying Biker's entire head with the golf club.
Afterward, Jacket visits Beard's customer-less bar. Beard comments that Jacket doesn't look happy, and admits he feels pretty bad himself, "something in the air, like something terrible has happened tonight," and comments that he "hasn't felt this way since San Francisco". This foreshadows that Jacket's failure to actually kill Biker will have repercussions for him that will lead to loss of someone he cares about.
A blood drenched Jacket emerges from the bathroom into an utterly trashed animal living room, blood trail leading to Rasmus. Don Juan says Jacket looks ill and should see a doctor, get some rest, and relax. Rasmus says that if Jacket insists on returning, he'll leave. Richard gives no answers, but tells Jacket this is their second to last meeting, and offers three predictions:
At this stage, and for the rest of his life, Jacket believes Richter to be under orders from the Russian mafia. He later learns that Richter is a masked killer just like him, but he never fully realizes (but possibly suspects) that the masked killer movement actually isn't angled from within the mob itself.
On May 27th, Jacket's apartment is completely free of pizza boxes and newspaper clippings, and The Girl has moved to sleeping on his spare bed instead of the couch. "Pat" from the Club calls Jacket in as a spare DJ. Notably the phone call says beer "is on the house." Jacket arrives at the dance club to find the body of the grasshopper-masked killer Carl and several Russian mobsters, one of which has a cell phone.
Jacket visits Beard's customer-less convenience store, which is now marked in the same manner as all other targeted locations. Beard says he has to tell Jacket something important, gesturing to the exploded-head corpse of Biker and saying "that did not happen" and that all of this "is not happening." He sees that Jacket doesn't believe him, and demonstrates as the screen turns to surreal static. The corpse of Biker is gone, but a blood stain remains, revealing that Jacket merely wounded Biker. A mysterious man, Richter, appears in the bathroom of the convenience store. Beard seems to "reset" and tells Jacket it's nice to see him, that friendly faces are "few and far between these days" and to help himself to whatever he wants. The surreal static intermittently continues as Jacket leaves.
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