- "There must be a word for this." "An impasse, sir. An impasse."
- The newspaper article concerning the start of World War One. The writer doesn't even try to pretend to know what the hell is going on in Europe, and points out that he's glad the United States is staying neutral... by selling weapons to both sides.
- Professor MacDougal trying to speak You No Take Candle to Nastas, who calmly points out (with a hint of Never Heard That One Before) that there was a school on the reservation and that he speaks fluent English. And MacDougal still kind of does it after that point.
MacDougal: (in exaggerated body language) Good morning, Nastas! Would you like to take off your slippers? Or skin a rabbit? *clears throat* I know, we cannot see the stars, but still, my heart is pure, and we meet, as equals! (to John) These savages must be spoken to simply in metaphores.
Nastas: No, sir. I grew up on a reservation and attended school.
MacDougal: Oh... lovely, heh...
- Edgar Ross' similar attempt: "DO.YOU.SPEAK.ENNNGLISSSH?"
- Which is followed by this:
Fordham: Uh.... yes he does, sir. He's the informant, Nastas! (chuckles)
Ross: Don't get snarky with me, Fordham.
- Irish's confusion as to whether the funny friend of his from Mexico was actually from Mexico, or from Canada.
Irish: I met an American guy. Saw him shoot a man. Drank with him in the village of Chuparosa. Funny guy... Or was that Canada...? No. That was Canada. Guy here, not funny, but he's real nice.
- Followed by this slice of fried gold:
Irish: So long, John Marston. You're an angry and a feck-ugly man... but not a bad one.
- While you're riding downriver with him during "We Shall Be Together In Paradise", one of his random lines during the battle: "I couldna have boned all your daughters!"
- The whole mission can be summed up as "The Gunslinger snarks everything The Alcoholic Butt-Monkey says for ten minutes while they float downriver on a deathtrap." It is possibly one of the funniest missions in the game.
Irish: Have I ever done you wrong?
John: No, but not through lack of trying.
- In the middle of a raging gunfight, Irish's thoughts apparently turn to Mexican prostitutes (or possibly an attempt to insult the bandits out for his head, but the prostitutes are more likely):
Irish: What's the word for cunt in Spanish?
John: You tell me. You must have been called it a few times.
- When Dutch's gang surrounds MacDougal's office and tells John to hand him over:
MacDougal: Please, sir, what are you going to do?
John: I'm going to hand you over to them and watch them tear you limb from limb.
- Likewise, the exchange right before this:
Dutch: You and your friend there, the professor... we're gonna kill the both of you.
John: Now why would you wanna do a thing like that?
Dutch: Oh I don't know... sport, I guess?
- John's Double Take when he sees McDougal crawling away.
- Sh-Sh-Shaky's witty r-r-riposte
Shaky: F-f-f-f-fucking f-f-f-fuck!
Irish: Oh, my virgin ears.
- When Marston, Ross and Fordham are taking Nastas to MacDougal's office:
Fordham: The man was thrown out of Yale for degeneracy.
- Those who find the sex scene this. Especially the girl's random shouting of Viva Mexico!
- Could be both. It comes completely outta nowhere, possibly prompting you to go "ARGH WHAT THE FUCK MY [family member of choice is in the room], DON'T JUST THROW THIS AT ME!". Then the chick goes Viiiiva Mehicooooo!~, and you can't help but laugh.
- Or, for a third possibility, you get horrified by the sex scene, but can't help but laugh at Reyes afterward.
Reyes : I like peasants. Don't you like peasants?
- Whiskey, which makes John Marston violently angry.
- Or optionally,drunk as a skunk!
- Pass by a prostitute while drunk. She'll proposition John. John will refuse, stating he is a man of principles or something about his wife. Then make him stumble around the bar until John collapses onto the floor in a booze-soaked heap.
- Irish's horse quality test
- One of Jack's random lines when skinning an animal for its fur is, "Let me take your coat, Ma'am."
- "Horse, meet idiot."
- " JACK'S GETTIN' AN AUTOMOBILE!" Granted, it would be even funnier if you could actually buy one, but oh well.
- When tying up a woman: "And they say romance is dead.
- In Armadillo, an old nun from Las Hermanas may give John a blessed cross. That could have been solely in the heartwarming category, as she walked straight through crazy Old West territory just to give it to John, if not for the fact that she then might then walk all the way through the saloon to stand outside and smoke a cigarette.
- Say what you will about Edgar Ross, but his increasingly nonsensical monologue about Dutch's anarchy at the beginning of the mission "And You Will Know The Truth" is pretty amusing, especially John's bewildered reactions.
- "A GLASS EYE?! ITS A GLASS EYE!" Poor Seth.
- This cartoon, which you can watch in Armadillo. The second guy is especially fucking hilarious !
- "Ain't ya got some peckers to be suckin'?" - Irish.
- Luisa believing she and Abraham Reyes are going to marry when the guy can't even remember her name.
Reyes: How do you know my young lover, Laura?
Marston: It's Luisa.
- Herr Muller: "You fucking cheat! You fucking looked at my fucking cards you fucking cheat!"
- The Walton's Gang member Link Huston that can be found in the Armadillo saloon and as a bounty target has some hilarious lines. He's about the only bounty target that, instead of shouting angry insults or threats at you when catching him and bringing him back to jail will instead laugh and make suggestive comments, such as remarking about you tying him up and saying he'll give you a kiss if you let him go. He's also the one you hear randomly shouting "Scum licker!" and "III'M coming for YOU!". Pick a fight with the guy and he may shout "Put it in me, come on, put it in me!" If you shoot Link and he runs for cover, it's both funny and sad as he might shout "DON'T HIT ME, MOMMY! DON'T HIT ME!"
- Also, when you've become so famous that people everywhere recognizes you and addresses you with name, bump into Link and he'll say "Oh Mr. Marston. Excuse me, Mr. Marston!" in a rather suggestive tone as well. That or "Kiss me. You won't regret it. Hehehe!"
- The mission "Who Are You To Judge?" has John retrieving a loved one named Lucy for a guy named Jeb. Turns out that Lucy is a horse. When you deliver her back to Jeb, the cowgirl that was looking after her says THIS:
"Life out here does funny things to people. I should know; my daddy kept goats."
- Your second encounter with Sam Odessa:
John: California is in the west. Just follow the setting sun.
Sam: (walks away) *snort* "setting sun"...
- It's pretty damn funny when you've spent the whole game fighting to be reunited with your family, to the point that when you finally get to ride up to the door of your home, most players probably expected a teary eyed and relieved Abigail to come greet him... instead the first thing she does is to run in fury towards John, immediately pounding away on him while shouting "You no-good, hillbilly piece of shit! I thought you was dead! I thought you was dead, John! Where have you been, huh? Where have you been?!" which makes you immediately wonder if you go through all that trouble only to find that John is a Henpecked Husband, (but fortunately she calms down).
- It can double as a Tear Jerker when you realize that Abigail wasn't being a nag, but rather, was being sincere. This is probably why, as she is so flustered and filled with grief that seeing her husband again only leads her pain to develop into a heartbroken anger.
- Marston finds Irish trying to rob a pair of nuns in Thieves' Landing.
Irish: *points gun at Marston* Who the hell are you?
Marston: *takes gun from Irish* I'm your old friend, amnesia. *pistol whip*
- West Dickens giving instructions to the crew for the assault on Fort Mercer.
West Dickens: Marshals of the law, when the shooting starts take that as your cue to....start awarding each other medals.
- "You get the smelly end!"
- John when releasing a hogtied person: "I'm going straight to Heaven for this!"
- For those who enjoy a bit of Black Comedy: Step 1. Travel to Torquemada. Step 2. Start pushing people. Step 3. Run to the far right side (besides the Five Finger Fillet table) and jump over the wall there, then go as close to the edge as possible. Step 4. Stand and watch while the people you pushed tries to chase you but instead ends up sending themselves screaming and plummeting down a 300 feet canyon wall. (Just don't push soldiers, you'll become Wanted and they'll shoot you instead).
- Abusing the physics engine can be hilarious. It's both entirely possible and freaking hilarious to push someone over a railing in this game, especially someone leaning or sitting on the rail itself. A fall from a second-story building won't necessarily kill the victim, but watching the reaction is comedy gold, as NPCs don't get a lot of chances to simply to fall off a ledge in this game. It's therefore possible to push a prostitute off the balcony of the saloon in Armadillo.
- John really doesn't like the automobile that he's riding in with Ross and Fordham, especially after it breaks down, leaving them open to an attack.
John: So much for this automobile of yours. If this is the future, God help us all.
Ross: It's not the automobile. A bad workman shouldn't blame his tools. Perhaps if Mr. Fordham maneuvered it with a little more finesse...
Fordham: I was trying to escape an ambush, sir!
John: Even if it was runnin' fine, they'd still have caught us. I can walk faster than this piece of crap! Give me a horse any day.
- In the early sidequest "Jenny's Faith" we get this gem of an exchange:
Jenny: Faith can move mountains. That's what it's all about.
John: You're trying to move a mountain?
- Rob a place and John might randomly shout "TAXMAN'S HERE!"
- "I GUESS THIS MAKES ME A GUNMAN!" After slaughtering dozens.
- The game actually rewards Video Game Cruelty Punishment: kidnap a woman, hogtie her, put her on some railroad tracks, and let an incoming train smash her to bits. You'll get a trophy/achievement for this.
- At the end of the mission "The Prodigal Son Returns (To Yale)", McDougal hugs John goodbye to which John's body language just says "Ugh."
- If a thief attempts to steal your horse, you can simply whistle and the horse will throw the thief off and return to you.
- Even funnier: The game rewards you with 50 honor for dismounting near a horse thief and letting them take your horse... at which point you're free to call your horse back to you without losing those 50 honor points.
- Marston shouting at the victim of a cannibal: "You broke this poor fool's leg!"
- While riding with Seth:
Seth: (to himself) Have you looked in the cave, Seth? (In weird, feminine voice) No, it's very dark.
John: What did you say?
Seth: I-I didn't say nothin'.
John: I just heard you say something.
Seth: You're a crazy man. You should get that head looked at.
John: Seth, I need someone who can get a wagon inside Fort Mercer. I was told you could help me, but I'm not sure you even know what day it is.
Seth: I don't. I can't even tell you what year it is.
John: I knew this was a waste of time.
- Your first meeting with Vicente de Santa and the Mexican government:
De Santa: What do you want, gringo? What are you doing here? Have you heard, there's a war going on?
Marston: My name is John Marston. I've been sent here to retrieve a couple of men. Can I speak to your commander?
De Santa: You want to talk to my boss, gringo?
Marston: I guess.
De Santa: Because I am not good enough for you?
Marston: No, sir.
De Santa: You think you're better than me? You come to my country, my poor little country, and you think you can be friends with the president?
Marston: No, sir. I am sorry, sir. Things must have come out wrong. Maybe you can help me?
De Santa: You'll be sorry, friend... (starts laughing) Relax, amigo. Relax. (still laughing) I had you.
Marston: Sure, somewhere between the threatening stare and the soldiers armed to the teeth, yeah, yeah you had me.
De Santa: Welcome to Mexico, amigo!
- This exchange between John and Irish:
John: Now, Irish. That machine gun of yours don't work. I find that very upsetting, don't you?
Which is why I was coming to see you when the drink got the better of me!
- In your first mission in Mexico you will, among other things, be asked by Landon Ricketts to shoot some bottles to practice your aim. Next to this is a drunk man sitting and drinking from a bottle that you can also shoot (the bottle that is). Doing this will cause the man to shout in a very upset voice: "Pinche gringo de mierdaaa!" ("Fucking American piece of shit!")
- A lot of Marston's taunts in Mexico are this, due to his limited Spanish vocabulary.
- "JOHN. MARSTON! REMEMBER MI NOMBRE!"
- "I'M GONNA KILL ALL OF YOU! TODO!"
- "YOU'RE ALL GONNA BE MUERTO!"
- "You must be the pendejos I keep hearin' about!"
- If you see a person taking a piss in the wilderness and go up close to him, he will understandably get mad and start yelling you out.
- Sometimes perfect timing can make for some hilarious scenarios, for example if you have a nun walk up and honour you while you have a tied prostitute on the horse, or have citizens run to you for help while you're close to the train tracks, causing them to get hit by the train and explode into gibs.
- Gameplay and Story Segregation kicks in when you can spend the entire game having John shoot hundreds of animals and he then tells his son Jack in one of the final missions to "Only kill what you need."
- Take a stagecoach drive and it can be funny to hear John's verbal outbursts if you ask the driver to go faster ("HURRY THE HELL UP") or slower ("I NEED TO GET OFF!")
- A small one, but when John is helping West Dickens with selling elixirs to a crowd, the former has John drink one and then asks him if it worked. John's line and the way he delivers is pretty funny.
West Dickens: Your eyesight is greatly improved, is it not?
John: [beat] If you say so.
- In the gameplay preview version, John simply responds with a deaadpan "Yep."