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  • While it has disastrous consequences for the game, the Irrational affliction gives some hilarious lines to the affected heroes. Here's some of them:
    Arbalest: Silence, my arbalest sings!
    Bounty Hunter: Bring me a small dog. So crunchy. Mmm.
    Crusader: I smell brimstone. Or is that hyacinth?
    Grave Robber: So many young gentlemen, so little propriety. Sigh.
    Hellion: Someone armwrestle me! ... COME ON, YOU COWARDS!
    Highwayman: Come, juggle these daggers with me! Hee heeee!
    Houndmaster: This is no mere dog, this is the first being to orbit our terrestrial sphere! note 
    Plague Doctor: My feet smell of gangrene! YOU - smell these!
    Vestal: Verse XVI: the meek shall... Lords, this scroll is heavy.
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  • Quotes from other afflictions can also be darkly hilarious. Here's a few more:
    Abusive!Antiquarian: (Attacking party member) Your mother should have done this to you a long time ago.
    Masochistic!Antiquarian: (Refusing to eat) I am fueled by the blood of my enemies, thank you.
    Selfish!Bounty Hunter: One hay-penny short... Someone is going to die.
    Hopeless!Crusader: (Refusing to eat) No... The Light says I need to lose a few stone.
    Abusive!Musketeer: (Refusing to perform camping skills) Has bumblebrains got themselves an owie?
  • Some of the Jester's quotes can predictably be a source of comedy, even while he's virtuous.
    Never been much of a leader, but I'll try... TALLY HO!
    (snort, spit) There, that's my opinion.
    They take me for a fool. ... Fair, I suppose.
    (whining) But I won't get any fighting if I move there! (This one is funniest if you imagine it with a "BUT MOOOOOM!" kind of delivery.)
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  • Some of the lines your characters have as they enter into various services can be pretty amusing. Take this one for instance, when a character enters the brothel.
    I need you, you, AND you! It's been a long day.
  • The Crusader's Zealous Accusation skill, which involves the Crusader pulling out a document and presumably accuse his enemies of something. And it actually physically hurts them. Made even better by how it makes the damaged sprites for the monsters seem like they're just really insulted.
    • Similarly, the Enraging Slight that the Manservants can do. Not only does the hero in question get insulted so badly that they take both health and stress damage, but they move forward, meaning they actually run at the Manservant in anger. Made even better by the fact that it's nothing more than a dismissive, backhanded wave.
  • The Narrator can, at times, be hilariously dissonant.
    Highwayman: (finds an intact torch in a sconce)
    Narrator: Wealth beyond measure, awarded to the brave and foolhardy alike!
    • or
      Hellion: (Activates "Adrenaline Rush", screaming in barbaric fury)
      Narrator: Soothed. Sedated.
    • The Narrator has a funny line when you discover a large amount of treasure. He initially impressed, then embarrassed that he was a bit too cheery.
      Narrator: Impressive haul! (sheepishly) If you value such things.
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  • You can get some just bizarre results from the RNG going. It is possible to, for example, have a character be repeatedly seduced by the magic of the Siren, and then gain Nymphomania and Love Interest at the end of the run, or a hero coincidentally getting the runs when a bas relief's "dark power" surges through them.
  • Some of the hero composition builds can be funny simply from how the game really doesn't expect you to stack 4 of the same hero, so you get things like Crusade or Clown Car builds.
  • Given the nature of the Occultist's Wyrd Reconstruction, it's entirely possible to have it heal 0 HP, and bleed the hero on top of that!
  • The Bone Courtier is a skeleton dressed in fine clothes, and one of his attacks consists of throwing the content of a wine goblet (which must be really bad since it inflicts health and stress damage).note 
  • The Sanitarium is a subversion of Bedlam House — though it looks like a frightening place, especially before you upgrade it, the medics there effectively treat and cure serious diseases and mental disorders within a week. Nonetheless, there's a bit of Black Comedy in how your heroes react to being treated there:
    "It's just a rash. Why do you need the knife?"
    "I place my trust in your gnarled, warty hands."
  • While engaging in stress relief, it is possible for a hero to end up refusing to leave and staying in that activity for another week. It is also possible for that hero to keep doing this repeatedly each week you come back, meaning that it is possible for your heroes to literally spend three or four or even more weeks engaging in nonstop gambling, drinking, prayer, or... indulging themselves in the pleasures of the flesh in the brothel.
  • Some of the best trinkets in the game are Ancestral trinkets, which are possessions of the Ancestor. These include the Ancestor's Pistol, the Ancestor's Coat, the Ancestor's Signet Ring, the Ancestor's Mustache Cream...
  • The loading screen usually comes with a general advice tip. Then we have this in the Courtyard.
    Eating bananas is a surefire way to get swarmed by mosquitos.
  • Usually, fighting the Farmhands of the Farmstead shouldn't be too comical, given they are people whose body was infected with eldritch crystals. However, there are two funny things about them. First is that when they get hit, it does look like they are dabbing, something which Red Hook has acknowledged too. Secondly, their Pause From Labor ability has them take a break from the fighting and take a tired pose, leaning on their hoes to brush off some sweat which is kind of bizarre given that they're husks now.
  • One of the buildings you can construct in the Hamlet is a Puppet Theatre which passively reduces stress for heroes staying in the Hamlet. Just the thought of a group of hardened warriors sitting around watching a puppet show is hilarity in itself.
  • The Hero Backstory Comics in a nutshell is essentially an Abridged Series of the comics that treats the rest of the game as though it were an MMO, complete with alternate interpretations of the characters and their actions.
    Abomination: The tattoo parlor fucked up the design I wanted, so I slaughtered everyone there.
    Antiquarian: I was chilling with this guy who was showing his GF some incense he bought from me. It smelled like shit, but then I realized I could probably get a rare antique if I looted it back, so I made the most financially profitable choice. The GF was a bit pissed at me for slashing open his skull though.
    Arbelest: My dad was about to get roasted in a massive flame war, so he gave me a crossbow and told me to become a professional Crossbow-Woman in a world with flintlock weaponry just to prove one of his arguments.
    Bounty Hunter: Some guy made fun of my helmet, so I butchered him in a public place.
    Crusader: I went from a nobody to a holy knight in an elite order of crusaders. It was really fun until the Crusade event ended, then everyone just started farming the “Lady and Small Child” boss fight over and over because the late game was shit. After I finally got the Holy Shopping List +4 to drop I bailed.
    Flagellant: I was begging for money but got beat up instead. Then I remembered “When life gives you lemons...”, so I just started sustaining myself off pain. Worked out great, saved me a lot of money on groceries.
    Grave Robber: I forgot to take the rings off my deceased husband before they buried him. Things escalated pretty quickly from there.
    Highwayman: I was ye old John Wick until I fell into the trap of grinding the “Lady and Small Child” boss fight. 20 hours later I still couldn't get that fucking shopping list so I gave up.
    Jester: I’m a living example of why bullying hurts everyone.
    Leper: I got all dressed up for a costume party only to accidentally show up at a funeral.
    Man-At-Arms: I fought through countless wars and survived being hit by a cannon, but I still start out as a level 0 scrub.
    Occultist: I found a really nice scented candle.
    Plague Doctor: I raised my hand but my teacher never answered my fucking question, so I murdered him and mutilated his body.
  • Level 5 Cove expeditions feature an enemy called the Squiffy Ghast, the Evil Counterpart to the Jester. To drive the point home, he slides to the front row to set up for a high stress damage skill that moves him to the back again, and he's also programmed to target the Jester first if there's one in the party. There's even an achievement for killing him with a Jester called "Mine Goes to 11". It's a pretty funny thought imagining the Jester and Ghast dropping everything just to have a musical duel.
  • The Cove's Giant Oysters are notably the only curio type in the game that's interactable with dog treats. Doing so gives the interacting hero +25 DODGE (somehow) and the resulting subtitle looks like it's lampshading the fact that the interaction was Crazy Enough to Work.
    "The oyster seems to like these..."
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