- Take a shot every time a named character is killed off.
- Take a double if it’s somebody you liked.
- Take a sip every time Dutch says something about having faith or a plan. Take another if it's "goddamn faith" or a "goddamn plan".
- Take a sip every time Dutch says "doubt". (Seriously, you'll drink a lot with this one, especially by the end.)
- Take a shot whenever Dutch calls someone "son".
- Take a shot every time Uncle refuses to help by invoking his lumbago.
- In "A Quiet Time", have a drink when Arthur or Lenny are shown drinking on screen.
- Take a sip every time Arthur says "sure" or "boy".
- Or anytime he says "calm down" or "easy, boy".
- Take a shot if Dutch or Miss Grimshaw call you out on not donating money to the camp.
- Finish the bottle if you're actually going out of your way to donate as much as possible to camp.
- Take a shot if Pearson greets you saying "haven't received anything from you in a while, Mr. Morgan" or "don't forget to go hunting, Mr. Morgan". (Take a double shot if you just came into camp with more than one carcass for him on your horse.)
- Take a shot every time Mary says "Oh, Arthur".
- Take a sip whenever Tahiti is mentioned by a gang member.
- Take a shot every time Dutch's plans go wrong.
- Take a shot every time poor Arthur coughs.
- Take a shot every time time Micah calls Arthur "Cowpoke" or "Black Lung".
- Take a shot every time you get ambushed. (Might cause alcohol poisoning in the Beaver Hollow chapter.)
- Take a shot every time Bill embarrasses himself.
- Take a shot every time Reverend Swanson starts a conversation with you in camp.
- Take a shot every time Reverend Swanson sings "I'll Never Get Drunk Anymore" (the "one night when I was frisky" song).
- Take a shot every time Pearson reminisces on his days at sea.
- Take a shot whenever a gang member smokes a cigarette or a cigar.
- Take a shot whenever a gang member monologues or sings at a campfire (outside of a party).
- Take a shot whenever you hear Dutch and Molly arguing.
- Take a shot whenever Karen is visibly drunk. Beware in the final chapter.
- Take a shot every time you have to shave Arthur, if you like the clean shaven or light stubble look.
- Take a double shot if you were actively growing a nice beard, mustache, or sideburns. If it was a Level 8 to 10 growth, finish the bottle, in tribute to the Hair Tonic you just wasted.
- Take a shot every time someone asks "who's there" when you return to camp, even if you only left a few minutes to go hunting or something.
- Take another if Arthur calls them "dumbass".
- Take a shot every time Trelawny addresses someone as "dear boy" or a group of men "gentlemen" or "boys".
- Take a shot every time something really terrible happens.
- Take a sip every time Micah acts like an asshole.
- Take a shot whenever Arthur insults, rebukes or complains about Micah.
- Take a sip every time you bump into someone in Saint Denis.
- Take a shot if you get a bounty for disturbing the peace or if your horse crushes them to death and you get wanted for murder.
- Take a shot every time you ruin a perfect pelt.
- Take a shot every time you drop your hat and have to pick it up or grab a new version of said hat off your horse.
- Take a shot every time you get knocked off your horse, or crash into something. Seriously, it doesn't matter how good you are, sometimes it seems like the game just hates you.
- Take a shot every time Arthur says “Okay, I’ll catch you later then.”
- Finish a pint whenever Arthur and any other of Dutch's Gang have to fight off an ambush.
- Take a shot whenever the game crashes. Take another if it’s during a story mission, forcing you to redo it.
- In the final chapter, take a shot whenever a gang member approaches you to lament about the camp's collapse.
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