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Kingdom of Loathing offers various modes that impose special rules onto the player. All are optional, and make things harder, but offer special rewards (and extra content in the case of Bad Moon and many Challenge Paths) if you follow them through to the end.

Game modes actually present in-game:

  • "Hardcore" is the game's own Hard mode. It has all the limitations of the Ronin phase,note  but extends them for the entire run. Additionally, it forbids you from using items, money, and skills from earlier ascensions; you can circumvent the last one by paying more karma to make those skill "Hardcore permanent". Being a "lifestyle" and not a "path", it can be activated in addition to all the modes described below.
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  • The dietary "paths" put restrictions to what items you can use. "Teetotaler" forbids alcohol, "Boozetafarian" forbids foods and non-alcoholic drinks, and "Oxygetarian" forbids all three.
  • "Bad Moon" is a special "moon sign" that essentially acts as a special game mode - and it's the only one that requires an "unlock" method: you can access it only if you never used any ten-leaf clovers in your previous run. Not only it's automatically set on Hardcore, but it actively suppresses many effects that normally carry between runs, to create a "level playing field". Since it's a "moon sign", it replaces all the bonuses normally given from other signs; and it has the effect of randomly subjecting you to "unlucky" adventures, which give you small bonuses and big disadvantages.
    • On top of that, there's "Kittycore": a Bad Moon run only using the black cat familiar. During this run you are not allowed to use ANY familiar other than the black cat, which does such things as preventing you from picking up items after a battle, preventing you from using combat items or skills, and reducing the experience you gain from winning a fight. Beginning any fight without the black cat even ONCE before stepping through the gash at the end of the game and ascending will void the "Kittycore" run. Completing this run will permanently unlock Bad Moon, eliminating the requirement of a clover-less run.
  • Special challenge paths were introduced in the summer of 2011, with new ones coming out every three months (although some of them are actually easier than regular). They are as follows—
    • Bees Hate You: The letter "b" is now your enemy. You take damage for every B in the names of your equipment, enemies become stronger for each B in their names, you can't use non-quest items with B in their names (and the quest ones hurt you), and bees randomly attack you.
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    • Way of the Surprising Fist: You become a Bare-Fisted Monk. You can learn impressive skills, but you can't equip weapons or off-hand items at all, and you have a vow of poverty which slashes how much Meat you earn and cuts off non-combat Meat gains.
    • Trendy: Any limited-time content that's more than a year old is unusable.
    • Avatar of Boris: You become a special class with its own skill tree. Mighty Boris can feast all day long and is aided by the versatile Clancy, but he Can't Hold His Liquor and will not even contemplate using any weapon but his trusty axe, Trusty.
    • Bugbear Invasion: Bugbears invade the kingdom, radically shaking up the quest structure and completely changing the end-game.
    • Zombie Slayer: You become a special class with its own skill tree. The name's misleading, though - you are a zombie. All you can eat is brains, you can't consume as much booze as usual, and you can summon hordes of the undead to aid you (while at the same time being limited to "undead" familiars such as the Hovering Sombrero or the Spooky Pirate Skeleton).
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    • Class Act: Skills that your class doesn't learn naturally are unusable.
    • Avatar of Jarlsberg: You become a special class with its own skill tree. Jarlsberg, the Great and Powerful, knows incredibly potent magic, but his rampant fear of germs prevents him from eating or drinking anything he doesn't make himself in his Cosmic Kitchen, and he won't contemplate attacking physically.
    • BIG!: You start the game at Level 15 (in a game where you're encouraged to fight the Final Boss at level 13). However, the enemies are tougher, too...
    • KOLHS: Your character is reincarnated as a teenager. They're forced to spend the first 40 adventures of the day in a specific zone, the Kingdom of Loathing High School, where all the monsters scale to your stats, and the school rules forbid hats and familiars over ten pounds. Fortunately, you can ingratiate yourself with one of three cliques depending on the skills you use. And after school, you can craft items from ingredients found while adventuring at the school, go on a photography side-quest for the Yearbook Club, or get some buffs.
    • Class Act 2: You start out with all and only skills from your chosen class, and are rewarded more for beating monsters and less for choice adventures.
    • Avatar of Sneaky Pete: You become a special class with its own skill tree. You are imbued with the legendary coolness of Sneaky Pete. Your sidekick is a talking motorcycle and you can drink booze like a fish. An audience is watching your every move and you need to manipulate the crowd to love or hate you to your advantage. As a downside, you are a very light eater.
    • Slow and Steady: Every day, you have exactly 100 Adventures to work with. No more, no less.
    • Heavy Rains: A massive flood makes monsters tougher to fight and sometimes washes away item drops based on the water level, wandering water-based monsters attack you periodically, and almost all bosses are also replaced by a water-based counterpart that are harder to defeat. However, at very deep waters you get the opportunity to learn new skills that let you harness the power of the storm.
    • Picky: You are limited to only 11 skills and 3 familiars. While it's actually not a challenge whatsoever to newer players as they may not even have 11 skills to pick from, it's crippling to seasoned players who've amassed hundreds of skills that they've come to take for granted. Imagine if you all of a sudden had to use a piece of charcoal and a rock slab to write your essay instead of a computer.
    • Actually Ed the Undying: You control Ed the Undying, the mummified ancient pharaoh final boss of the Level 11 MacGuffin Quest. He is armed with a slew of new spells, curses (one of which involves actual swearing), and assistants, but what makes him truly unique is his uncanny ability to indefinitely resurrect himself as many times as he wishes. Furious with the jackass adventurer who stole his MacGuffin (read: you, as in your player character), he sets out on a journey to reclaim his beloved artifact. He initially is quite weak for new players, as he understandably lacks a stomach or liver due to the mummifying process and instead relies on spleen to generate the majority of his adventures; however, Ed possesses a kind of Magikarp Power in that he becomes an unstoppable machine once the player manages to upgrade Ed's frail body.
    • One Random Crazy Summer: Monsters now get adjective(s) that modify their difficulty and drops.
    • Community Service: As a bit of a Take That! to players who wanted the game to take less real-life time, all the normal Council quests (including the Naughty Sorceress herself) are gone, replaced with eleven Community Service tasks, each of which takes one click (but up to 60 adventures) to finish.
    • Avatar of West of Loathing: An early self-plug for Asymmetric's game West of Loathing, which wouldn't actually be released for more than a year after this path was current. You play one of the three classes in West of Loathing (Cow Puncher, Beanslinger, or Snake Oiler) and play through the game using skills unique to each class. In addition, you fight three tiers of three types of monsters (cows, rodeo clowns, and snakes) that provide the most benefit to their respective class.
    • The Source: After taking the red pill (because the blue pill is just a jellybean), the player plays through the game as normal, except stat gains from edible items are gone and monsters provide less stat points on defeat, and on occasion, digital rain will appear, warning of the appearance of a Source Agent, a powerful enemy that can only be fought with path-exclusive skills taught by not giving the Oracle spoons you can find in various locations and using the phone in Spookyraven Manor. The final boss replaces the Naughty Sorceress with One Thousand Source Agents.
    • Nuclear Autumn: You've become a nuclear mutant incapable of using any consumable item greater than size one, your stomach and spleen are reduced to a maximum capacity of three, and your liver a maximum of two.note  In addition, several important NPCs are inaccessible and you will periodically get radiation sickness that will reduce your stats, forcing you to either rest or use a special item to cure it. On the flipside, you also have access to a special radiation shelter that provides a variety of useful benefits, and you can earn a currency called rads to trade for a variety of exclusive and powerful skills.
    • Gelatinous Noob: You're a gelatinous cube that's assumed the approximate shape of a human and aspires to become a real person. You're a unique Moxie-based class that can't eat food, drink booze, or consume spleen items, isn't affected by enchantments of equipped items, and can't access guilds. However, instead of normal consumption you can absorb any item that can be stolen in PvP to acquire powerful passive skills and/or extra adventures and stats, and can absorb equipment to gain their enchantments for the rest of the day. You also get three MP-expensive but extremely powerful combat skills.
    • License to Adventure: You're a secret agent for the LI-11 organization, tasked with saving the day from a variety of supervillains. You can't eat or use a familiar, your maximum drunkenness scales with your level, and you can't drink any booze that isn't served in a martini glass. In addition to the usual Council quests, you must periodically complete missions to clear out supervillain lairs or else be disavowed by your superiors, causing a crippling debuff to all stats until you continue your mission again. You also gain access to a special form of currency called "social capital" which can be used to purchase exclusive passive skills from LI-11 Headquarters.
    • Live. Ascend. Repeat.: The entire game is altered to eliminate randomness wherever possible. Banishing and tracking monsters doesn't do anything, food, booze, and spleen items always give average results, combat encounter rate can't be manipulated by skills and items, there are no wandering monsters, the RNG is seeded so that every player will have the same monsters and encounters on the same turn number in each zone, and item drop rolls are always exactly 50 out of 100.note 
    • Pocket Familiars: You cannot use familiars in the normal sense. Instead, you use a team of 3 familiars and pit them against other monsters instead of normal combat. Guilds are unavailable and you have no access to any permed skills from previous runs. The Cake-Shaped Arena is replaced by the Poképorium, where you can gain Pokédollars from leveling up familiars to spend on path-specific items and hats. Finally, almost all boss battles are replaced by PokéFam battles with Jerry Bradford.
    • G-Lover: The Spiritual Antithesis to Bees Hate You. You love the letter 'g'. Equipment without the letter G in it gives no bonuses, and you can't use non-quest items or familiars without the letter G in them (and quest ones hurt you).
    • Disguises Delimit: Everyone wears a mask (you included); each type of mask grants specific bonuses to the players or monsters that wear it. You can swap masks with your opponent by using a special "Swap Masks" skill.
    • Dark Gyffte: You become a special class with its own skill tree. You're an undead vampire, which has a limited pool of HP that can be recovered only through sucking blood, passive regeneration, or resting into your coffin. On top of that, you cannot use familiars, and you're constantly hunted by vampire hunters. Skills consume HP instead of MP, and cannot be bought; instead, you can equip or unequip them whenever you rest, lowering or raising your maximum HP in the process.
    • Two Random Crazy Summer: Items now get adjective(s) that grant them random bonuses. These bonuses replace the regular effects.
    • Kingdom of Exploathing: The planet has been destroyed by a Space Invader, destroying all areas that weren't quest-relevant, immediately unlocking all areas that are quest-relevant, and making the game harder in other minor ways.

Special dungeon boss challenges:

  • Some bosses in the multiplayer dungeons (Hodgman in Hobopolis, the Mother Slime in the Slime Tube, and Necbromancer in the Haunted Sorority House) reward speedrunners with special items. However, two bosses impose special challenges to speedrunners:
    • To reach Hodgman in less than 1100 Adventures (which is required to get his rarest item), you must avoid fighting his lieutenants. The problem is that every undefeated lieutenant will grant a different bonus to Hodgman, making him harder.
    • Mother Slime's attack stat decreases the more time you spend in the Slime Tube. So, speedrunners will fight a harder-hitting boss.
  • Mother Slime also has a second challenge: defeating her without triggering a form change. (Form changes are triggered when you cause more than 500 points of damage in one turn.)
  • All the Dreadsylvania bosses have a "hard mode" version that is triggered when you confront them while either wearing certain items; or being under certain effects.
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