''Hotline Miami'' thrives on sociopathic, black comedy. If you're inclined to view it from that frame of mind.
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!!''Hotline Miami'':
* Just look at the cover art. Richard, Rasmus and Don Juan are gazing upon a scene in an ever-enigmatic fashion. Jacket has just butchered a Mafiya member. He's standing guard with Girlfriend in one arm, a fire ax in the other, and ready to take on ''all of the mook's comrades''... and to the left, Biker is leaning slouched back against a car. With one leg crossed behind the other. Bored. Reading a grot mag titled "BOOBS". Barely paying attention to the carnage right in front of him, if at all. His random appearance in this panorama is quite amusing.
* Once the initial shock of NightmareFuel wears off from seeing the corpses of the people you've killed show up in various places, some of the things said corpses say are quite funny. One calls you out, either insinuating that you're stupid for looking at him or that [[UnusuallyUninterestingSight there's absolutely nothing remarkable about a talking corpse]].
-->'''Corpse/Hallucination:''' What the '''[[PrecisionFStrike fuck]]''' are you looking at?
* The Police Chief's first and final speech. It's almost as if he's [[TemptingFate Tempting Fate]]. What makes this especially funny is that, considering the point of the game where this happens, the Chief would already know who Jacket is and be aware of how big of a threat the man is, yet he casts it aside like it's all nothing.
-->'''Police Chief:''' Okay, boys! The [[DoNotTauntCthulhu bastard]] will be here any second now. It's time for us to [[VerbalIrony show him]] what we're made of. Remember your training, and [[TooDumbToLive play it safe!]] Follow protocol, and we'll [[TemptingFate all make it out alive.]]
* Some of the achievement names are quite humorous, hinting at BlackComedy.
** The game actively mocks you for getting all the achievements with an award titled "Achievement Whore".
** If you [[KickTheDog kill 99 dogs?]], you'll earn an achievement titled "Dog Lover".
** Die 1000 times? '''[[WhatTheHellPlayer You deserved it]] [[TooDumbToLive for your incompetence.]]''' Here's an achievement titled "Karma".
** Beating chapter five with your own fists (especially if you're wearing the [[GoodOldFisticuffs Tony mask]]) will give you the achievement titled "These Are My Guns".
** Taking out a mobster who's sitting in the toilet with a fireaxe will earn you "[[ToiletHumor Smell Something Burning]]".
** Last but not least, getting A+ in all chapters will give you an achievement titled "Get A Life".
* It's possible to be ''right on top'' of a mobster and watch them fruitlessly unload their mags on you—ImperialStormtrooperMarksmanshipAcademy at its finest!
* While one hell of a JumpScare, getting run over by the van in "Deadline" can be downright ''hilarious'' if you're unlucky enough to be caught in its path.
* A rather dark (and if you [[DevelopersForesight found out the hard way]], frustrating) example, but after The Father decides that it's BetterToDieThanBeKilled in the final chapter, if you make the mistake of standing right next to him as he pulls the trigger, [[TakingYouWithMe he'll wind up (unintentionally) taking Jacket with him too]]!

!!''Hotline Miami 2: Wrong Number'':
* [[RabidCop Pardo's]] [[MemeticMutation memetic]] line "I was born with thick skin.", in response to Johnson's question. Particularly because Pardo immediately [[ChangeTheUncomfortableSubject changes the subject]] as for Johnson to not refute his absolutely BS statement.
* One of [[AcroFatic Jake's]] masks is the Dallas mask, which allows to use nunchucks, and blindly swing them around like an idiot as [[FatBastard the Confederate cock]] kills every damn mook in sight.
* Although incredibly dark, Evan reaching his [[RageBreakingPoint breaking point]] and [[ThereIsNoKillLikeOverkill proceeding to punch the shit out of whatever mook you've pinned down until their face is nothing but a bloody mess]] is quite absurd. Especially considering that you can keep punching the mook long after they're dead, to which after that your own death would be nothing but [[LaserGuidedKarma karma.]]
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