Shadows Over Loathing: How to Obtain the Evilest Ending (Five Easy Steps)

Similar to the bovine taint from the previous game, you gain Shadow Taint levels by consuming the accursed items you find in shadow holes, rifts, or anywhere else really.
Unlike West of Loathing, however, the counter is seemingly infinite- it’ll just keep going up and up as you eat more items. You only need five to get the “evilest ending” where you swallow the world whole in your shadow, but don’t let that stop your wicked dreams!
As you level up your shadow taint, you can talk with the freaky shadow creatures you randomly encounter, turning them into friends, and they’ll give you an item or exp. You can also remove the weird items found inside if you have the right level of shadow taint! There will also be more shadow orbs and new rifts as well. Finally, you will be able to solve the shadow magic problems in the story with your own, higher level shadow powers, and unlock Alphonse, a gatorman buddy.Note that once you’ve “opened your eyes” by reaching level 3 of shadow taint, there is (probably?) no way of going back, as you now loathe the un-cursing machine, thus removing your ability to lower your taint level. You also lock yourself out of talking to certain NPCs, and hobos will no longer wish to speak to you (except for Obie, for some weird reason).
Once you get supercharged with the shadow taint*, you are locked out of obtaining the buddy-specific ending achievements.

*see the perks section of this guide

If you want to go full in, you can choose to NOT un-curse all of the cursed items, Jessica none the wiser (yes including the fedora, just go back into your room anyways when Jessica stops you).
Doing so, the cursed items keep all their prior effects, and make you feel pretty evil.
Here’s what they do:

• Cursed Fedora, will let you bypass certain random encounters by speaking forbidden words
• Dangerous Pocketwatch, lowers a target’s stats by 13
• Cursed Compass, leads you to shadow item encounters
• Cursed Key, open any locked object (yes even the black house gate)
• Cursed Sickle, deals your muscle +13 spooky damage
• Cursed Haunted Duck Call, deal spooky damage and cause bleeding- both equal to your mysticality (obtained by throwing the duck call in the H*** Hole; will also scare the any ducks)
• Cursed Fishing Rod, deals your muscle +3 spooky damage (will also sometimes fish up shadow items upon use, found on the S.I.T bridge)
• Cursed Book, upon reading will grant you special shadowy perks*

Here’s a list of Shadow food items:

• Wine, grants 2 of every elemental armor
• Beer, grants 7 physical armor
• Mead, grants 70% increase in meat drops
• Milkshake, grants 1 mysticality and 2 ap
• Hot Dog, grants 1 muscle and 5 to your melee attacks
• Pickle, grants 1 moxie and 5 to your ranged attacks
• Salad, grants 1 mysticality and 5 to your magic attacks
• Elixir, grants 1 muscle and 11 maximum hp
• Grease, grants 1 moxie and 50% increase in item drops

And here’s the physical items you can snag from rifts:

• Skullcap, grants 13 physical armor (in the Gilmore house bunker)
• Chalice, grants a perk* (in the fishmother lair under the bridge at S.I.T)
• Loop, grants more shadow creature encounters
• Shorts, 50% increase in item drops (tentacle house)
• Egg, hatches into a familiar (basement below barbara’s hut, meaning you have to do some chores)
• Mirror, swaps stats with an ally or opponent once per fight (in the vampire bar on the boardwalk)
• Coin, grants 100% increase in meat drops
• Rat, familiar (present day sandwich basement; interact with the basement in the past then return to the present to shovel it open again, cannot be done once you’ve solved the town’s problems)
• Apple, increase all your stats by 13 once per fight (cherry orchard, by the wormfather)
• Hammer, deals 5 spooky damage to all enemies (S.I.T hexquarry, by the important machine)
• Briefcase, grants a forbidden perk increasing your class’ respective stat by one as you read the documents within (by the rune circle in the S.I.T library)
• Rift Fragment, can be turned into a sweet necklace if you move the accessory shop onto the street (Zimmer’s house)

Combat items:

• Rope, stuns one enemy for a turn
• Clarinet, reduce one enemy’s stats by 13
• Bomb, does 13 spooky damage to all enemies

*see the perks section of this guide

There are several available perks and skills, most from the Cursed Book (whose title is too long to write, honestly), and a few other perks here and there.

Miscellaneous perks:

• Forbidden perk, increases one of your stats by 1 (gained from the rift briefcase)
• Shadow-Charged, changes the ending (gained by absorbing the mysterious evil pillars)
• Shadowy Waters, grants 10 maximum hp and 3 hp regeneration (obtained from the shadow chalice- also turns your head into a fish)
• Haunted, gives themed dialogue options (prologue)

There are three skills granted by the book:

• Shadow Chomp, deals 5 spooky damage and heals you by the damage dealt
• Shadow Embrace, deals 13 spooky damage to an enemy and also yourself
• Shadow Vortex, steal 1 muscle, mysticality, and moxie from each other combatant

And six perks:

• Occlusion of Shadow, elemental armor challenges are easier
• Suffusion of Shadow, stat challenges are easier
• Collusion of Shadow, you start combat with three shadow creatures on your side
• The Shadow’s Vision, grants 1 mysticality and 5 to magical attacks, but minus 10 to hp
• The Shadow’s Vanity, grants 1 moxie and regular familiars (essentially non-shadow familiars) will not aid you in combat
• The Shadow’s Protection, grants 1 muscle and 5 physical armor, but minus 1 ap

Taking all the nine perks/skills from the evil book grants you an achievement!

• Alphonse will sometimes randomly find shadow items for you.
• No more candy from the nice hardware store man :,((( (thank you fillanator)
• If you put P O O P in the rift guarded by the dean it makes a “special” noise
• If you have a level 5 shadow taint, you can absorb your class’ rival and take their cool hat during their final encounter! Neat!
• When you open your eyes, they’re full of the same starry material as all the other evil things. You probably already knew that, but it’s still a fun fact.
• Most NPCs, especially quest NPCs will not react to your sudden evilness, which is funny.
• Interacting with yourself in mirrors after opening your eyes, your reflection will say “perfect, never change” and you’ll respond back with garbled shadow speak.
• Getting St. Polycarp’s blessing while tainted will cause you to respond with “it stings a little!”
• Approaching the Church of St. Polycarp with a high level of shadow taint will cause you to be struck by lightning.
• High levels of shadow taint will affect the environment, e.g. more dead trees and an omnipresent black fog
• As you gain more shadow taint, your dreams will be increasingly haunted by demonic eyes and mouths.
• You can kiss one of these mouths!

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Thanks to Felix-sishou for his excellent guide, all credits belong to his effort. if this guide helps you, please support and rate it via Steam Community. enjoy the game.