All 4 Endings in Single Playthrough
I will not go into every separate choice as there are different guides that describe how to locate specific items or to activate certain events (like compelling Irene Sanders towards suicide).
Rather, here is a list of alternatives that I did on my second playthrough, which astonishingly granted me all four choices in the end.
1. Never drink alcohol
2. Read all unholy books(3 of them)
3. Tell bradley the truth about Marie Colden’s fate.
4. Always choose answers in R’Lyeh language(9 of them, 10 if you count obligatory answer while “communicating” with Leviathan in prison).
5. Make Irene Sanders commit suicide.
6. Accept Algernon Drake’s offer for help in bookstore.
7. Save drake at the end of the fight with the Shambler.
8. While conversing with Leviathan chose option “struggle” in “underwater prison” sequence.
9. Refuse to accept Leviathan knowledge, first offer.
10. Refuse to accept “the Truth” – Leviathan knowledge, second offer.
14. Refuse to take medicine while hallucinating in whaling dock.You will take it anyway, this is intended, but YOUR CHOICE matters.
15. Refuse to eat meat while hallucinating in whaling dock.You will take it anyway, this is intended, but YOUR CHOICE matters.
16. Refuse to take the gun while hallucinating in whaling dock.You will take it anyway, this is intended, but YOUR CHOICE matters.
11. Spare Bradley.
12. Save Mitchell, the bar owner, by getting him medkit from the Warehouse.
13. Examine Cat’s dead body after you have saved Mitchell.
This choices triggered ALL FOUR endings in my playtrough. If they don’t do the same in your’s, I have no idea why.
Have fun with this wonderful game.It’s not a waste of time even when you replay it. I must be aware that Leviathan’s monologue/dialogue has more sense once you replay the match.

