I wrote this a couple years ago in 2016 for the Themes section of the Hotline Miami 2: Wrong Number page on this wiki. I'm not sure it's becoming a wiki, but I do stand by this old analysis having just re-read it. Posting it here for posterity should I decide to remove it from the wiki proper.
Hotline Miami 2: Wrong Number represents a massive shift in tone from the original game. The colors have shifted from hazy neon pastels to stark dark purples lacking any kind of visual blur to them. Sun Araw's psychedelic music is completely omitted, replaced with tracks such as a melancholy untitled menu song by The Green Kingdom, calm remorseful songs like Modulogeek's Around, and exhausted on-the-job beats like Old Fox Future Gang's Guided Meditation. The characters, in stark contrast to Jacket and Biker, are largely identified by their job titles or actual names instead of their possessions. Dialogue, while unanimously terse and filled with natural awkward silences, is more prevalent and each character uses it slightly differently.
This variety of expanded and diversified characteristics and focus on a wide array of lifestyles creates a sobering effect next to the original game. This parallels the shift in primary setting from 1980's to the much culturally calmer 1990's. Violence in 1991 feels aimless: the Russian mob is gone (similar to how the Cold War was basically over by this point in history), and the Fans often note that the people they target prior to Death Wish are disturbingly similar to themselves ("Kinda like this place, huh?"), even having similar colored and decorated hang outs (Down Under) and a shared interest in exercise and recreational marijuana.
Drugs are touched on much more soberly in Hotline Miami 2, focusing more on the kinds of people who use, transport, and attempt to control them. Alex is a recreational user of marijuana and her technician brother Ash frequently bashes people on the basis of being junkies. Police Detective Pardo (based on a real MDPD officer who declared himself a soldier and murdered six people) is shown cracking down excessively hard on Colombian drug smuggling (Dead Ahead) and this is later revealed to be a function of his own personal self righteous power fantasies. Pardo tries to have a meeting with the Russian mob immediately afterward, implying he did the job to earn their trust, or is perhaps angling to take them down too just as brutally.
Flashback missions to a fully fictional Hawaii warzone perhaps most analogous historically to America's involvement in Nicaragua trace the source of violence acceptability in the other direction: here even Barnes and Daniels, wholly likable people with friendly personalities, also are expected to and do enjoy executing and beating prisoners (Ambush outro).
The over exaggerated Hawaiian jungle -- complete with panthers as a triple origin story for 50 Blessings, the Brandon mask, and the Father's pet panthers -- is heavily used to give context to events in the subsequent settings, but also to draw an analogy between humans and the animal conditions that created them. When the Russian Henchman asks to go home in Execution, he also mentions he wants to go to the jungle. The absorption of humans into animal traits is a theme that's been with Hotline Miami since the first game's tutorial, and the endgame for Hotline Miami 2 naturally builds this to a head where characters become the animals they pretend to be.
Throughout all of this the player's impulse to catalog it manifests in the character of Evan Wright, who is also based on a real Miami writer who writes about real Miami criminals. Due to the focus on lifestyle, however, the writer is entirely defined on his sinking unhealthy amounts of time into retrieving overlooked information. Exposing schemes with his information isn't so much his concern as much as the fact that he could write a popular book with that socially trending information and make money to support his family. The exact gigantic scale of the impending disaster is never made clear to the Writer or the player until the last minute of the game and by then choice to abandon the investigation or quickly publish his narrow view of events has already been made; in fact, even choosing to continue to investigate isn't done so with the urgency required to stop the ending from happening anyway. The emphasis here is on natural personal blind spots. Similar to Biker in the password ending to Hotline Miami people are shown to have limits on what they care about and things like the global and political rarely factor in.
Writer's perspective on other characters is noticeably limited: he has a close friendship with Pardo due to a mutual interest in garnering fame, Manny fears that Evan knows too much (Caught), but it only ever amounts to Evan calling him a douchebag. In the Bar of Broken Heroes, Evan refuses to press Biker for details as it would require giving the extremely unhealthy looking Biker 200 dollars of booze money, and Evan determines this would be wrong.
Flashes to the 1989 setting from the first game detail the lives of Jake and Richter, both of which play up different aspects of the original game's Jacket. Jake is the patriotic pizza eater who hates his job loves his car and can't hold a steady relationship, and Richter is the torn man backed into a corner with everything to lose. These characters allow for much more distilled tones than Jacket and have vastly different soundtracks and feels. Jake is summed up by the fact that one of his songs is named Quixotic: he's a naive idealist who's comical detachment from reality is ultimately his own downfall.
Richter on the other hand is a story of personal growth and maturity as he progressively cools to his extremely dangerous jobs and earns the happiness of himself and his mother. Richter relies on pity and chance to survive his prison whacking (the pipe drop in Release), but his abilities and quick reactions under stress are what really make him win the day. His levels are cramped fast moving frenzies which train in him the jumpiness that got Jacket's girlfriend killed in the original game. This sympathy building emotional conflict is compounded by his dying mother for whom he is the sole caretaker. The spectre of some long gone "loner" father hangs above the large house and Richter himself is unemployed. Inadequacy issues and fatalism hang over all of his scenes, levels like House Call mark a somberly playful transition into the purple shades of the 90's, a depressing transition foreshadowing an ending that he'll be the first to see.
As Richter finally fully trades in his innocence for competence in Release the game transitions to the Son, who also has inadequacy issues surrounding his dead kingpin Father but has few qualms wresting the drug throne back from the Colombians, at least until the ultimate futility of trying to please a dead man dawns on him (Blood Money); however, he continues onward seeing no other path for himself.
He confides in his one friend, the Henchman, that "as soon as you let yourself get attached to anyone, you're fucked." The Henchman, who wears a tan similar to the Hawaiian soldiers indicating his middle age, is made increasingly nervous by the Son's dangerous aspirations to alter the balance of criminal power in Miami, and asks to be allowed to leave. The Son very reluctantly gives him one final mission, but is already advertising the prospects of coming back as he gives him a free sample of a new product (which are pills, rolling with the increasing pharmaceutical usage in the nineties). Henchman leaves, and must pass a much more expensive car to get to his own. Henchman is reclaiming a recently defecting chop shop that happens to help fix the Fan's van.
Subtly conveyed themes of poor people striving for material gains, and of the older generation fearing to be swept up completely by the new, abound as the aging Henchman murders a dozen teenagers with a skateboard surrounded by impossibly expensive cars and older cars being scrapped for their good parts, just as the Henchman says he feels he'll get killed any day now and rejects the more youthful aspirations of the Son; he then dreams of a new car instead of his girlfriend. He awakes to find that his final pay and his car have been stolen by her and that the Son was right. Dejected he takes the pills and attempts to call either Mary or the Son but in his disoriented state dials a completely wrong number.
The Son plays out his war alone and after a climactic assault on the Colombian headquarters he has finally brought about a return to the monolithic multicolored drug fortresses of old, and in doing so attracts the same anti-Russian Cold War sentiments, desperately looking for ground in the confused and barren 1990's. There is now nothing to distract him from his aimless inadequacies and like his grandfather he feels he's grown into the throne like a wheelchair. He tries to find solace in the friendship of Henchman but he's already been taken by this new setting. Everything unique has been bled out of it and all that remains are his monotonous army of faceless goons. In this mindset he turns to hallucinogens and hits them hard.
As the Fans attack looking for some kind of vindication of their own feelings a confused Son does the only thing he knows how to do: kill everything until he wins. Reality seems to rewind back to that warzone where all was accepted but the camaraderie is no longer there, only the jungle (office plants warping into full blown jungle foliage) and the wild animals that took his friend, glimpses of empty Russian rituals and piles of money destroyed and consumed instantly without thought. As he kills each animal one could easily recall Richter's father's room, decked out in pelts and heads as decoration and personal trophies.
The sudden killing of every character pans over near still images of their final moments, most unaware entirely that they're about to die. The contrast in how each character goes out ironically generates an extremely distilled value of lifestyles and happiness in the face of oblivion. The characters who die with loved ones are the characters with the ability to form them, and the characters who die alone would have never reached out anyway.