This is the biggest drinking game I've done so far, partly because it's so easy and mostly because Lost is a badass show. I'm sure I could've come up with plenty more rules but any more felt like overkill; if you think of a good one that's not on here, feel free to add it to the comments. I also didn't bother giving any rules special "Chug/Take a shot" status because I figure you'll already be drinking quite enough - but of course feel free to upgrade any of the less-used rules to that level if you wish. Lastly, I should add that four or five of these rules I cribbed from here.
Universal Rules:
Take a drink...
Whenever any of The Numbers are mentioned or appear (4, 8, 15, 16, 23, 42).
Whenever anyone says "Others," "Dharma," "Widmore," "Hanso," "Hatch," “Driveshaft,” or "Oceanic.”
Whenever anyone stares out at the ocean.
Every time you hear whispers in the woods, or hear the various noises the smoke monster makes. Drink twice if you see the monster.
Whenever two character get into a brawl.
Whenever there's that "whoooshing" sound right before a flashback or flash-forward.
Whenever you correctly shouts "flashback" just before one starts.
Whenever a character appears in another character’s flashback.
Whenever one of the Oceanic 815 extras has a line. That includes Scott and Steve.
Whenever anyone cries.
Whenever it starts raining.
Whenever anyone embarks on a journey into the jungle.
Whenever someone dead re-appears (in flashbacks, dreams, as a ghost, or what have you).
Whenever someone dies.
Whenever there’s a close-up of an eyeball.
Character-Specific Rules:
Take a drink...
Whenever Jack calls another character by name. Drink twice if it’s Kate.
Whenever Sawyer calls anyone a nickname or makes a pop culture reference.
Whenever Sawyer reads a book.
Whenever Kate holds a gun.
Whenever Jin says something in English.
Whenever Sun lies.
Whenever Claire says “My baby” or “Aaron.”
Whenever Sayid does something ridiculously awesome or conveys more common sense than anyone else.
Whenever the camera shows Sayid’s awkwardly long fingernails.
Whenever Charlie gets angry.
Whenever Hurley says “Dude.” Drink twice if he says “I’m not crazy.”
Whenever Desmond says “brotha”.
Whenever someone hits Ben/Henry Gale.
Whenever Juliet gives one of those infuriating looks of pitying/condescension.
Season-Specific Rules:
Take a drink...
In Season 1:
Whenever it’s revealed why someone was on the plane.
Whenever two main characters meet for the first time.
Whenever Sawyer has the letter in his hands.
Whenever Locke explains something to Boone.
In Season 2:
Whenever Michael says "I'm gonna get my boy/son back," "They took my son!," or "WAAALT!!" (So basically, whenever Michael has a line.)
Whenever they input the numbers into the computer.
Whenever Ana-Lucia acts like a massive turd.
Whenever Mr. Eko tells a story. Drink twice if it's a biblical story.
In Season 3:
Whenever Desmond talks about Charlie dying or has a vision of him dying.
Whenever an Other besides Ben or Juliet has a line.
In Season 4:
Whenever Faraday acts nuts.
Whenever one of the Oceanic 6 is revealed.
Whenever we're introduced to someone on the freighter.
Whenever Locke acts like a terrible leader.
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So this one doesn't get back on the air for a while, but it's just way too easy to come up with a drinking game for me to resist. It practically writes itself. By the way, I'm sure there are other versions of this floating around, but I didn't want to be influenced by any, so I haven't looked.