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  • Dirtwater starts out with a long line of empty lots on the right, marked by "Lot Available" signs. If you walk in front of them, they fill about 3 or 4 screens' worth before stopping at a sign that says "Not a lot available past this point".
  • The running gag involving spittoons. The narrator is disgusted any time you dive into one, and describes in great detail the disgusting filth you're fishing through in hopes for an item. By the last one, the narrator gives up and just eggs you on as you stick the whole thing on your head and proceed to wear it as a hat.
    • Unless, of course, you never touched a spittoon through the entire playthrough, in which case you have the option to ask the narrator what the hell he's talking about. This prompts the narrator to react with surprise, then start asking you whether you're sure you want to pass up the spittoon hat—refusing the hat will leave you permanently unable to acquire it, but gives you +5 to all stats in exchange.
      • However, this doesn't prevent you from going back and fishing through the other spittoons, so you can get the Spit-Free AND Spittoon Hand perks at the same time.
    • There is exactly 1 Spittoon in the Gun Manor DLC. Unlike the other times, your new pardner Florence will take notice of your...habits around spittoons. Moreover, also unlike other times, this Spittoon is absolutely clean; the manor's staff had meticulously cleaned it and you find nothing. Given Florence's lines, your character apparently broke down into tears and went into a fetal position cuddling the spittoon not long afterwards.
  • If you go to the (Re)Boot Hill Cemetery, you'll find a tree with a keyhole in its trunk and three graves with a safe in each, note that the people in those graves were part of a tontine and that inside of each of the safes is a piece of the key that unlocks the hidden compartment in the tree which holds the tontine's treasure. The idea was that the last living one of them would get the others' pieces, assemble the key, and keep the treasure, but it turns out that they all died at the same time, meaning that the treasure is just lying there for anyone (i.e., the player) to find the key and take it.
  • The terrible puns at the Old Mission:
    Sister Mary: I... I'm Sister Mary. [...] Our mission's, er... mission, is to protect three sacred relics. I'm the Relic Keeper, it's my specific job to look after them.
    Player: Wait... do they call you Memento Ma—
    She shows you the ruler she keeps tucked in her sleeve.
    Sister Mary: No. They do not.
  • Late in the game, you can use [an El Vibrato Chronokey to open a temporal portal. Through the portal is a jumble of areas, including the ruins of a pyramid with a jawbone that quietly whispers one word to the player: UNDYING!
  • The description of the bandit gun: "A device to replace bandits with other bandits until the last bandit who gets replaced with nothing." It works on multiple levels, too!
  • The "Stupid Walking" perk, which, as you might have guessed, replaces your walking animation with several silly ones like swimming on the ground or pretending to ice skate, is one of the very first perks you can get in the game, way before you actually get used the game's sense of humor. This means that it's very likely that it will get you caught off guard and urge you a few laughs.
    • There's even some unique animations involving your lantern when in dark areas, such as hopping around on it like a pogo stick or riding it like a horse.
  • During your journey from your family farm to Boring Springs, you apparently did something that got you banned for life from Topeka. The real kicker, though, is that we never actually get to know what that "something" was, so you can imagine it to be just about as funny as you want.
  • A Beanslinger can summon a Bean Golem in combat. The game states that the bean golem gets progressively larger as you level up that skill; however in actual gameplay the size of the bean stays the same. The difference being:
    • A bean with a face.
    • A bean with a frowning face.
    • A bean with an angry face.
    • An angry bean with a cowboy hat.
  • A skeleton campaigning against the Necromancer, while ranting about how new skeletons are giving a bad name to natural-born skeletons. He will give you a "Necromancers, I Hate'em" button if you agree.
  • A goblin Elvis.
    Player: I don't know what is real any more.
  • "Well, that's one group of demonic clowns that won't be troubling people any more, and boy you did not expect to be thinking that sentence today."
  • You can get your tongue plated with silver for two thousand meat. Once the operation is complete, you request a full refund and immediately receive one, proving it works.
  • Opening a locker and getting attacked by a skeleton covered in shaving cream. Your character posits that this is because the guy's buddies stuffed him in there with the cream as a prank, and gets confirmation from the skeleton screaming essentially that explanation in so many words as he attacks.
  • Wasco's "jokes" are actually hilarious...just not at all for the reason that they should be. Especially his botched delivery of the "horse walks into a bar" joke.
  • If you actually read all the plaques in Shaggy Dog Cave, then walk all the way back out to your pardner, they'll have something new to say: The Aristocrats! Your character is suitably perplexed.
  • One of the game options offers to turn on color blindness. The game is entirely in black-and-white by default, save for some colored text. Its description also comments "You never know".
  • The individual cases of how the books you've read are "discarded" afterwards.
  • One of the potential encounters in the wild is with a skeleton Bigfoot, with one of the options being to intimidate him, which requires maxed out intimidation. Should you try to scare him, the player character will respond that you must be dumb if they think they can scare them. The skeleton Bigfoot and player character will then laugh at you for thinking it would actually work.
  • The entire ordeal of helping the hungry ghost in Gun Manor. You need to make him a bowl of chili, restrain yourself from adding a gun to it (guns being a traditional chili ingredient that killed him in the first place), and give it to him. But hold on, there! That's living chili, and he can only eat ghost chili. So how do you make ghost chili? Why, you kill it, of course! You either stomp it to "death" (if Ruthless) or smother it with a pillow. Finally, he is able to eat it and pass on.
  • The same string of jokes is used again when dealing with the One-eyed ghost lady. You'd think getting her a new glass eye would be enough, but logic ensues and it falls out of her ethereal body. She then takes a hammer (don't ask) and smashes it, producing a ghost glass eye. This then gets double-subverted in that it doesn't give her the fulfillment of being "complete" until your character realizes that, since she's dead, her bodyparts should have followed her into the afterlife. Turns out it got pushed way back into her skull so she has to plop it back into place like "one of those puzzles where you have to get the marble in the hole".
  • At least two members of the Gun Manor Museum Staff decided to milk the hauntings for all they're worth, one by essentially taking a paid vacation in one of the guest rooms of the Manor and another got himself "trapped" in a room filled with booze. Both are quite pissed when you "free" them from their "Captors".
  • The Art Book is this on several levels.
    • The sheer audacity of creating an art book for a game in the Loathing universe.
    • The concept art is typically shockingly well-rendered, while the final art is the typical Loathing stick figure style. See Doc Alice for example.
    • On the subject of Doc Alice, in the simplification of her artwork into a stick figure, two details were deemed relevant enough to remain; Her hair, and the bottle of alcohol she carries. It helps set the tone for the setting as a whole very well.
  • Choosing to show your varmint skinnin' knife to a grizzled skinner gives your character the opportunity to do the "that's not a knife" bit before getting cut off by the skinner, commenting that the bit is stupid because they're obviously both knives.

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