Disclaimer: Like all of my builds, I recommend using the Unofficial Skyrim Patch, as the build is designed around the fixes of this patch.
Additionally, I attempt to make all of my builds viable for Legendary difficulty, so if parts of the build feel overpowered to your taste, feel free to omit as you see fit.
“Sheggorath, you are the Skooma Cat, for what is crazier than a cat on skooma?”
~Clan Mother Ahnissi, Words of Clan Mother Ahnissi to her Favored Daughter
Born in the desert sands of Anequina, The Skooma Cat is a devout follower of the teachings of the Daedric prince of madness Sheogorath, desiring little more than spreading debauchery and chaos wherever they go. Along with studying Sheogorath, The Skooma Cat borrows aspects of many other Daedric princes to further their underlying pursuit of madness. In particular, The Skooma Cat borrows the indulgence in Sanguine, the manipulative nature in Mephala, the disregard for welfare in pursuit of change in Boethiah, and pursues the teachings of Nocturnal to best become an unseen, and therefore impossible to predict, force of madness as much as they are a living conduit of madness.
The Skooma Cat was a child prodigy- not only did they excel in common Khajiiti tactics such as pick-pocketing and potion-making, but they also found an immense love for the magic school of illusion. The Skooma Catwould spend hours every day crafting new illusions and turning invisible to prank their family and friends, much to their chagrin. Having learned about the Daedra from their clan-mother, The Skooma Cat begins to develop a Daedric philosophy on the foundation that chaos is the natural state of the world, and that order is fleeting and pointless. This is supplemented by their grandmother's constant yarns of the day Elsweyr seceded from the empire, proving in The Skooma Cat's mind that regime is impermanent and that the individual comes first. Therefore, The Skooma Cat favors personal independence and freedom over structure and peace, and following this philosophy, they inevitably one day leave their clan in northern Anequina to travel the world, first merely preaching about the wisdom of Sheogorath before eventually succumbing to his teachings, constantly indulging in fights, skooma and alcohol, and other particularly indulgent activities.
While traveling towards Skyrim to share their teachings with the embattled Nords, The Skooma Cat is arrested on the Skyrim border with Cyrodiil for a countless list of broken laws. Upon realizing they are the Dragonborn, The Skooma Cat decides to take immediate advantage of their newfound gift to spread more insanity and chaos wherever they go, emboldening their powers. Not particularly concerned with saving the world, The Skooma Cat is happy to take their time pursuing the dragon threat in Skyrim, though as their powers grow, The Skooma Cat's desire for chaos transforms into a desire for being the root of all chaos, and as such the dragons' presence threatens their rightful place in the world. Alduin must be stopped, not so that order can be restored to Skyrim, but so that all order can be disrupted through The Skooma Cat's direct control. Whether this desire to be the center of events is the direct influence of Sheogorath or other Daedric princes, or simply a cat who's had one too many skooma, The Skooma Cat's desire for change, disorder, and debauchery is constant, if not growing all the time.
Skills: Heavy Armor, Illusion, Pickpocket, Smithing, Enchanting, Alchemy
Stat Distribution: 1 Magicka, 3 Health, 1 Stamina
Shouts: Unrelenting Force, Disarm, Whirlwind Sprint, Marked for Death, Dragonrend
Standing Stones: Start with Warrior, then move on to Atronach.
Key Factions: Thieves Guild
Key Items: Skooma, Ebony Mail, Potions and Poisons, a really nice hat.
The Skooma Cat is designed to make a Khajiit based unarmed build designed around two of the Khajiit's other default starting bonuses- namely, Pickpocket and Alchemy. Our goal is to make our enemies act as irrationally as possible. We can make them fight each other using Illusion magic, sure, but why stop there? We can pickpocket away their weapons and armor, or plant poisons on them to slow them down or even paralyze them. Do you want to see a bandit clan punching their completely paralyzed and naked chief? Do you want to see Dwemer mechanisms tear each other apart while you quietly sneak away? Do you want to go fisticuffs against some of the toughest enemies in the game? The Skooma Cat has you covered.
We fight dirty. If an enemy is facing us, we might consider our options, and even slip away if his sword looks too big. If his back is to us, however, I personally favor knocking him down, and then jumping on his neck where the bones snap with a gratifying crunch. Of course, it is up to you and your personal style.
With smithing, alchemy, and enchanting all available to us, it is not necessary to go fully clad in the best armor you can find. Consequently, we are avoiding the entire right side of the Heavy Armor tree as most of those perks require some form of a matching set. Fists of Steel, which increases unarmed damage based on the base armor rating (note: not the improved armor rating) of your gauntlets, is necessary for an unarmed character, and Conditioning will save us inventory space for our potions, poisons, and skooma.
Illusion is the only school of magic we care about. Frenzy spells are going to be one of our main sources of chaos and debauchery. Additionally, Muffle and Invisibility are going to replace sneak, allowing us to get very close to people and plant poisons on them or pickpocket away their weapons and clothes. Calm spells are also convenient in that they allow us to pickpocket enemies who are already hostile to us. Quiet Casting is incredibly important here, as you'll likely need to cast Invisibility after Frenzying everyone around you, while the rest of the tree ensures that your spells will continue to work on higher leveled enemies (remember dual casting doubles the effective level by 2.2). Muffle will eventually be replaced by the Muffling effect of the Ebony Mail.
I feel this tree is underutilized by many assassin characters. And granted, it makes more sense to poison a weapon than it does to throw poisons into people's pockets. But we don't use weapons- ever. Poisoned is arguably the most important perk in this tree, as it will let us kill enemies or otherwise manipulate them without anyone around us noticing. Extra Pockets gives us more carry room for poisons and potions, and Misdirection and Perfect Touch let us steal weapons and armor, respectively.
I'm well aware that people will object to using all three crafting skills- given that this is an unarmed build, I feel it is necessary to show at least what is, in my mind, the most effective way to play this build. That said, this is the least essential skill of the build. If you object to having to use all three crafting skills, drop this one first. Improving your gauntlets does not improve their unarmed damage, so the point of smithing here is to 1. increase your armor rating for the early levels and 2. make higher tier gauntlets available at early levels. Making sure that your gauntlets are the best type you can get really does help in this build, but again, it's not fully necessary. I still highly recommend using it to allow yourself to wear something other than a helmet while hitting the armor cap, as that opens up a lot of interesting gameplay options in headwear, or at least lets you wear a fancy hat. Arcane Blacksmithing is also at least somewhat necessary to improve the Ebony Mail, but again you can choose to not use that as well.
Enchanting and Alchemy are necessary in this build. The pair will allow you to craft fortify alchemy gear into fortify enchanting potions, and repeat as necessary to craft the best poisons and potions you can. With the Unofficial Skyrim patch, this is limited to a fortify alchemy of 33% on 4 pieces of gear, but it's still completely necessary if playing the game on Legendary difficulty. Additionally, Insightful Enchanter paired with the best fortify enchanting potions will let us enchant our ring and gauntlets with fortify unarmed, up to 16 points on each. Unarmed damage is hard to find, so you have to take it where you can get it. You can even use this loop to replace smithing to some extent by crafting the best fortify smithing gear and fortify smithing potions, but this will take some time to get.
The single most important crafting skill by far. This is your main method of healing, so Physician and Benefactor will help you keep your health topped off. Resistance potions are also incredibly helpful since the only source of magic resistance in this build is its choice of standing stone (with the Aetherial Crown you can optionally take Lord for an extra 25% resistance). Obviously Poisoner is important as well, as we want our poisons to be as effective as possible. Do keep in mind that you can abuse pickpocketing and paralyze poisons on trainers- pay a trainer to level you in a skill, then move into stealth and paralyze them. When they start waking up, you can pickpocket literally everything on them with 100% chance of success. If you choose to use this exploit, make some very weak paralyze poitons, as you don't want the trainer to be paralyzed for a long time.
One quick note:
Again, in regards to using all three crafting skills, trust me when I say the build strays far from being overpowered for the difficulty it is intended. We have no weapon skills or weapon enchantments, nor do we have weapons that are improved through smithing (improving gauntlets does not increase the damage they deal). There isn't even a fortify unarmed potion*. Our main sources of damage are fists and pickpocketing poisons, and you can't pickpocket many of Skyrim's enemies (Dragons, Dwemer mechanisms, Draugr, oddly enough most things that begin with the letter D). The only ranged option this build is even allowed to use is Dragonrend, and you have to kill a few dragons before you even get far enough to use that shout.
*Worth noting is that, wtihout the unofficial patch, the Fortify Marksman potion DOES improve unarmed damage, as it applies to all combat skills, not just Archery. If you really want, you can exploit that. I can't stop you. No one can stop the mad god.
Too much magic can be dangerous. M'aiq one had two spells and burned his sweetroll. ~ M'aiq the Liar
Here are all the spells in the Illusion school we care about:
Frenzy Spells: Fury (Novice) -> Frenzy (Adept) -> Mayhem* (Master) - Creatures and people up to level 6/14/25 will attack anyone nearby for 30/60/60 seconds.
Calm Spells: Calm (Apprentice) -> Pacify (Expert) -> Harmony* (Master) - Creatures and people up to level 9/20/25 won't fight for 30/60/60 seconds.
Muffle (Apprentice) - No noise from armor for 3 minutes.
Invisibility (Expert) - Invisible for 30 seconds; breaks by most actions.
*Note that these Master Illusion spells have a very large radius (250 ft) and can be used right as you enter a dungeon to affect almost everything in it.
Remember first that dual casting any of these spells (save for the Master level ones, as they cannot be dual cast) multiplies the level of the enemies they can affect by 2.2. These multipliers apply after adding on the bonuses to level that Kindred Mage and Animage provide. People up to level 79, animals up to level 74, and undead/mechanisms up to level 59 will be able to be affected with all the Illusion perks and dual casting- you can improve this reach if needed using fortify illusion potions, but in my experience it's not necessary.
As for the Master Level spells, they have one major use. Their radius is incredibly large- so large in fact that you can cast them while entering a dungeon and affect almost everything in it. Additionally, any target that is too high level to be affected by Mayhem or Harmony will show up on the top left of your screen informing you that they are too high level. This is incredibly useful as it lets you prepare for fights ahead of time. Harmony is particularly hilarious if cast in the middle of a busy city, such as Whiterun- you can level from 90 to 99 in my experience, and accrue no bounty in doing so.
Seeing the ferocity of the Khajiiti warriors, Ra'Wulfharth could not bring himself to put them to death. Using the roar that Lorkhaj had given him, he spoke to Masser and Secunda, to move to their fullness in the sky. The Khajiiti warriors became Senche, but Lorkhaj stripped from them all reason.
~Sonia Vette, The Tale of Dro'Zira
Foritfy Illusion enchantments are helpful in reducing the magicka costs of dual cast Illusion spells. Fortify Unarmed enchantments are fairly self-explanatory. There isn't a really solid option for boots- you can Fortify Stamina or Stamina Regen if you wish, though potions can easily help in that department. I find the utility of Fortify Carry Weight makes more sense, as you can just use that extra room to carry stamina potions. If you choose to omit the Ebony Mail, you could also consider the Muffle enchantment.
Let's talk about the Ebony Mail for a second. Many people dislike this armorpiece for stealthy characters due to it being both heavy armor (as stealth based characters typically use light armor or no armor) and for the issues it causes when trying to stealth around hostile enemies. It does 5 points of poison damage per second to all enemies in melee range, and it muffles you. Though I cannot personally vouch for how it performs without the unofficial patch, I can say personally that it has not messed up any pickpocketing opportunities, even on enemies who I used the Calm spell on. What I will say is that this does only seem to work as long as you're invisibile, not just sneaking, and as long as the enemy is not hostile at that moment (e.g. not a red dot on your compass). On enemies that are hostile, you will need to be extra careful as the Mail can give your position away if you get within melee range. All of that aside, it's a very nice boost to damage that has the additional effect of being able to kill lesser enemies while you deal with big threats. If you want this armorpiece, do Boethiah's questline to the end. I recommend using the Calm spell on Boethiah's Champion if you want some fun bonus dialogue that most people don't even know about.
Finally it is worth noting that if you align with the Volkihar Vampires in Dawnguard, you can get a quest that rewards you with the Ring of the Beast. This ring gives you 20 unarmed damage and +100 health. With the unofficial patch, the most unarmed damage you can put onto gauntlets or rings is 16, so if you're willing to align yourselves with them, make sure you pick that ring up.
Now for the other main aspects of the build:
The only weapon you should ever use is The Wabbajack from Sheogorath's quest. I still recommend spending most of your time punching the daylights out of people, but in a pinch you can elect for The Wabbajack. You could optionally also use Sanguine Rose, but only if you fight the Dremora you summon, and not for any actual assistance.
Unrelenting Force is good crowd control and is worth using just to hurl enemies off of cliffs. Disarm puts other enemies on your level, though it isn't as effective as stealing their weapons outright as it is limited to lower level enemies even at three ranks. Still worthwhile early on. Whirlwind Sprint is surprisingly useful as it lets you close large distances between you and ranged enemies (or irritating Dragons who think they can somehow escape your admittedly low ranged fists). Marked for Death is useful against incredibly pesky high level enemies like Ancient Dragons or Drauger Overlords, and probably the most helpful of the shouts listed here. Finally, Dragonrend is self-explanatory. You don't have a ranged weapon, so waiting for dragons to land can be a pain.
The reason we choose Warrior at the start is to level Heavy Armor quickly. This is so we can obtain Fists of Steel early. It also has the advantage of giving you an early boost to Smithing, which will allow you to make gauntlets you wouldn't normally find at your level. Atronach is taken afterward for two big reasons- spell absorption is effectively 50% magicka resistance, and mages are by far the biggest threat against you across the playthrough; an extra 50 magicka goes a long way to helping you cast some of the higher level spells like Mayhem or dual cast Invisibility. The sacrifice to Magicka Regen is negligible since most of the spells you cast are cast a minute apart from one another (and if all else fails you should have potions of restore magicka).
Aside from basic restore X potions and potions of resist X, you should consider these two combinations:
“Elixir of Lifegiving”
A simple but effective healing potion brewed from everyday ingredients.
Fortify Health + Restore Health
Brewed using Blue Mountain Flower and Wheat
“Salve of Deft Hands”
This salve reduces all friction between your hands and your target’s pockets, making you more effective at pickpocketing. The salve also grants the user many restorative properties, though healthier skin is surpisingly not one of them.
Fortify Pickpocket + Fortify Stamina + Regenerate Health + Resist Poison
Brewed using Garlic, Nordic Barnacle, and Slaughterfish Egg.
There are many viable paralysis, slow, and health poisons you can brew in this playthrough. Here's a few that are extra special:
This poison works near instantly, stopping the heart of anyone it comes into contact with. Handle with care.
Ravage Health + Lingring Damage Health + Weakness to Poison
Brewed using Deathbell, Giant Lichen, and Skeever Tail
“The Shot in The Arm”
This hallucinogenic poison is quite rare and sought after among alchemists and thrill seekers. It renders mages near useless and causes some mild damage to the digestive tract. Also makes the user paranoid and prone to foolish decisions. Drink responsibly- which is to say, not at all.
Frenzy + Damage Health + Damage Magicka + Damage Magicka Regen
Brewed using Falmer Ear, Hanging Moss, and Human Heart
Exposing the imp stool fungus to human flesh doused in slaughterfish egg albumin causes the mushroom spores to attach to the nervous system of most humanoids, causing paralysis and interrupting most bodily functions.
Paralyze + Damage Health + Lingering Damage Health
Brewed using Human Flesh, Imp Stool, and Slaughterfish Egg.
Quests to Complete: Daedric Quests (Sanguine, Boethiah, and of course the Cheeseman himself Sheogorath), Thieves Guild questline, any brawl challenge in a tavern.
Factions: Thieves Guild, Dark Brotherhood, Volkihar Vampires (optional)
Before engaging in combat, survey the area (Khajiit power Night-Eye can help here) and see who has armor or weapons you can steal. Cast Invisibility (and Muffle if you don't have the Mail or muffled boots) and start taking what's yours. Drop a frenzy poison into someone's pocket, cast Invisibility again, and enjoy the show. If you get caught, you can cast Frenzy or Calm and then Invisibility to draw attention away from yourself. Once your enemies are weak, join the fray and start swinging your fists. You can take out any particularly difficult enemies silently by dropping health poisons into their inventory beforehand as well, and paralytic poisons are helpful against single powerful targets, allowing you to wail away at them while they take a nice nap. Some of the tactics you can use include:
Invisibility -> Pickpocket (Perfect Touch) -> Frenzy (or Frenzy poison) -> Invisibility
Steals the clothing of an enemy, sending them into a spiral of confusion and rage that leads them to attack every enemy nearby.
[Invisibility -> Pickpocket (Misdirection)] x Number of Enemies -> Mayhem -> Invisibility
Steals the weapons of all nearby enemies and forces them to fight each other with fists.
Frenzy Poison -> Invisibility -> Pickpocket (Poisoner) -> Invisibility -> Dual Power Attack Punch
Frenzies an unsuspecting enemy to attack another, allowing you to deliver a critical punch.
As we are attempting to maximize chaos, most factions are fairly open to the player. Thieves Guild pairs well with the selfish nature of the build as well as the skills focused on, and is arguably the best at creating chaos. Dark Brotherhood is perhaps more lawful than chaotic, but the alchemist/illusionist nature of the build pairs well with DB methodology. The Companions are not as complimentary to the build, particularly since the character would much rather punch someone to death than eat them as a werewolf, however the beauty of any selfish/chaotic roleplay is their nature of spontaneity- why not join a society of werewolves and become one yourself, just to see what it's like? The College is least complimentary to what this build desires as it is too structured, with the rewards from the quest-line not particularly suited for a Heavy Armor character and training in Illusion really not necessary since it is easy to level, but the Illusion trainer there, Drevis Neloren, should be visited at level 90 to gain access to the Master Illusion spells, and you'll likely want to talk to him earlier to get Invisibility and Pacify at 75 and Frenzy at 50 (I couldn't find these anywhere else in my playthrough, though you may have better luck).
The Civil War can be sided either way or ignored entirely- ideally in the way the player perceives as being the most directly beneficial to themselves (political considerations should be thrown out the window). Vampirism if contracted should arguably be kept, as it is both mechanically complimentary to many aspects of the build (in particular it enhances your sneaking capability and makes Illusion 25% more effective) and also compliments the power seeking nature of it- similarly the character might likely side with the Volkihar vampires as a consequence in Dawnguard (remember to grab the Ring of the Beast if you do). That said, if you've got a cure disease potion on you, don't be afraid to use it to cure Vampirism if it's something you don't personally want.
Finally, hoard Skooma by the truckload, or just consume all of it that you happen to come across- any mod that adds drug effects to Skooma is recommended but not necessary here. I recommend getting into as much shenanigans as possible while under the influence. Honestly, just have fun going around punching the daylights out of people, Frenzying your enemies, poisoning people, stealing their weapons and clothes... and your choices should manifest naturally.