The Alistair

A fool by any other name

(UPDATE: After Tim’s seal of approval I’ve re-edited the Alistair for more consistent terminology across the class, and reigning in some of her more outlandish abilities. I think it should be ready to play for anyone foolish enough to do so!)

(Update two: This will be the last change I make until the class gets some playtesting. Uncanny Eye now adds its bonus to attack AND damage, rather then either or, as was the case with the first version of the class. I decided that considering any damage based melee class will have no trouble outshining the alistair round to round getting one big attack in per combat wasn’t going to break anything)


Alistairs are unlike other adventurers in that they are actively sought by adventure. Alistairs forever find themselves falling into cursed rabbit holes, accidentally killing witches, having their half-brothers stolen by goblin kings, being willed magic rings, finding demons inserted in their chests or having armored knights ride through their homes while they are trying to sleep. Obscure gods, however, sympathize with them (they are often born to powerful families), and an Alistair is a boon to any party. Some Alistairs wear striped stockings or pointed shoes. In human fables they are often known by the names Jack or Alice, and all races maintain numerous legends about heroes who had no business taking to a hard life of adventure in the first place.

Although they begin their adventures untrained and naive, Alistairs are fast learners, and high level Alistairs are known for their sagacity and cunning.

In game terms the Alistair relies on luck, unusual abilities, and deus ex machina to see them through. Many of your most powerful abilities can only be used a handful of times over the entire life of your character. The ebb and flow of the Alistair is to remain unnoticed until the perfect time to pounce, not unlike a Rouge. However you are even more fragile then a Rouge, and must pick your opening carefully. Out of combat you will find yourself often with powerful ways to circumvent obstacles, but be wary of the new path you’ve set yourself on because it could be quite strange. Making allies with the dormice may have seemed like a clever way to learn the goings-on at the castle, but will their inane quests to slay cats and seek out discarded food be worth the hassle, when you could have just greased the palm of a guardsman like a good, honest adventurer would? Be careful of these self-made pitfalls, least you prove why, when translated from the texts of The Red and Pleasant Land, Alistair simply means ‘The Fool’.

Quick Build
You can begin play as an Alistair quickly by following these guidelines. First, make Charisma or Dexterity your highest ability scores, followed by Wisdom or Constitution. Alistairs are not fully in control of their own fates so if you feel spread thin, like butter over too much bread, that’s normal. Second, choose either the Nobility or Urchin background.

Hit Points: 1d6+Con
Armor: Light
Weapons: Simple weapons, plus the rapier, short sword, and improvised weapons (see Improper Handling below)
Tools: Any one
Saving Throws: Dexterity and Charisma
Skills: Chose three from the following: Acrobatics, Animal Handling, Arcana, Deception, History, Insight, Investigation, Medicine, Perception, Persuasion, Religion, Sleight of Hand, Stealth

You start with the following equipment, in addition to that granted by your background
(a) a rapier or (b) a short sword.
Typically this weapon mirrors your background. If poor, it is a suspiciously clean and ornate weapon hidden under a board in the cottage you share with your drunkard uncle, that hints at your family’s once-noble linage. If rich it is a battered weapon of war passed down from an adventuresome grandparent, and shows not everyone in your family lived with their nose turned up at such gruesome activities.
(a) a light crossbow with 20 bolts or (b) a bag of 20 pieces of hardened foodstuffs, each approximating half a day’s rations.
(a) a hefty iron skillet or (b) a cracked-but-mostly-functional spyglass, worth approximately 50gp in scrap parts.
(a) an explorer’s pack or (b) a diplomat’s pack.
A suit of padded armor, one item of your choice from the adventuring gear table not worth more then 25gp, and one additional trinket.

A note on ability scores: Alistairs find benefit from a wide range of ability scores. They often fight in melee, but tend to favor Dexterity over Strength. Dexterity also improves their armor and aids in remaining unnoticed. Their hit die is low, so they benefit from Constitution. Intelligence will allow them to make greater use of History and Investigation, which they can gain expanded use for. If they gain spells though their travels Charisma is their spellcasting ability, and aids in their impressive wordplay. Finally Wisdom improves the all-important Perception skill, which Alistairs can also gain expanded use for. Keep in mind the gaining of these expanded uses is not for you, but for the fates that be, to decide.


In times of unusual stress Alistairs may become Exasperated. This Exasperation causes fate to take notice of the Alistair, and then to aid her. The Alistair says or thinks something like “Oh I can’t conceive how I ever fell into this deplorable circumstance!” or “We are indeed doomed and the rats will gnaw our eyes.”

Practically speaking, an Alistair may express Exasperation once every game session (as games focus almost exclusively on stressful times, these represent the periods during which the gods are most likely to take notice). When this happens roll the dice.

At 1-5th level roll d4, at 6-7th level roll d6, at 8-9th level roll d8, at 10-11th roll d10, at 12th level and higher roll d12:

1- Jack had let his trusty sword guide him, but it lead to only an old oak tree. Sighing with despair he leaned against the tree, a knot depressed, and the passage to the dungeon below opened.

A secret door is revealed where none had previously been detected. If the GM has made no provision for a secret door, it leads to the nearest unexplored area.

2-The Alistair realizes she has something in her pack, her hair, or otherwise secreted about her person. The object can be anything non-magical and generic (a key, not the key) that exists in the setting and that is small enough that the Alistair could reasonably have it hidden it in her current condition or smaller than a breadbox, whichever dimensions are smaller at the time. The Alistair may choose what this is.

3-An ordinary animal—cat sized or smaller—appears. The Alistair cannot directly control it but it will not under any circumstances hurt the Alistair.

4-A fact about the situation at hand occurs to the Alistair—a piece of local or monster lore, perhaps something she read or was once told in a parlor or a lesson or in a kitchen.

5-Someone of the Alistair’s choice falls down. (Line of sight.)

6-The weather in the immediate area changes in a way decided by the Alistair—the change is general and may not be targeted (no aimed lighting bolts or gusts of wind).

7-A nearby creature is charmed by the Alistair for an hour. (Line of sight.) Boss-type creatures are not immune to this effect, but the Alistair’s charms do not extend to her party, nor does this mean the Alistair will have any control over the creature beyond they look upon the Alistair favorably.

8-An inorganic device or object of the Alistair’s choice breaks. (Line of sight.)

9-Something not ordinarily able to talk (GM’s choice) begins to speak to the Alistair.

10-Creatures present complete forget the Alistair is there for as long as the Alistair takes no obviously violent actions and can continue to make Wisdom saving throws (DC approximately the average passive perception of creatures in the area -5, aka at disadvantage) every minute.

11-Someone is sent to fetch the Alistair out of her current predicament. If there is an obvious candidate from among the local NPCs (giant eagles, a friendly knight…), that’s who it is. If there isn’t, then: hey GM, time to make up a weirdo. The NPC does not automatically have the ability to extricate the Alistar from the situation, s/he merely appears as close as is plausible.

12-Someone or something of the Alistair’s choice begins to shrink at 1 foot per round down to playing-card size. (Line of sight.)

These effects are considered divine magic and can be countered as such.

Improper Handling

You are very skilled with improvised weapons—at level 1 you are considered proficient with anything you pick up that is not normally a weapon. Small items can be thrown for 1d4 damage with a range of 20/40 (rocks, hard candy). Larger lightweight items are one-handed weapons dealing 1d6 damage, and have the light property (wooden spoon, wine bottle). Heafy items you can wield in one hand deal 1d8 damage (iron skillet, a big rock). Anything that would require two hands to wield does 1d10 damage (barstool, wagon wheel). These items generally deal bludgeoning damage, but may have other damage types at the DMs discretion.

Uncertain Destiny

The only thing Alistairs have in common with one another is that they are unpredictable. At first level and again at levels 3, 6, 9, 13 and 17 roll twice on this table. You gain the listed ability, and most give descriptions of their effect if rolled twice. If an ability cannot be gained again you lose the roll until your next level-up, if you can remember! Additionally many of these abilities grant you Advantage or a double Proficiency bonus with a skill. If you do not have the listed skill then ignore the text as written, and you are now Proficient in that skill.

1 Alice was then reminded of something she’d noticed before… You gain proficiency in a new saving throw, or double your proficiency in a save you already possess. You can gain this ability a total of four times, after that it is a wasted roll.

2 Jack liked pies, although sometimes people did not want him to have them. You can use your Perception skill with double Proficiency bonus to locate foodstuff of any kind. Rerolling this ability allows you to find organic matter of any kind with the roll. After this it is a wasted roll.

3 She closed her eyes and said the words as she’d been taught…You have learned one magic-user spell, which can be from any spell-casting class. Determine the spell randomly, rolling a d8 to determine level. If the spell is of a level you could feasibly know you can memorize it as if you were a Sorcerer, otherwise it works once, that’s it. Charisma is your spellcasting ability.

4 Her aunt had mentioned them … You have advantage on rolls to identify the faction or function of any aristocrat in any land. If rolled a second time you are cousin or niece or otherwise secondhand related to 1d4+Cha modifier NPCs of your choice, assuming you can explain a feasible familial relationship. These NPCs don’t have to be chosen right away, but if you forget how many you had socked away the DM is under no obligation to compensate you for this. Rolling a third time adds 1d4+Cha more NPCs to your extended family. After this it is a wasted roll.

5 All that hiding in the dumbwaiter has finally paid off. You know secrets. One of two kinds of secret, to be precise: either a piece of useful lore about a legendary treasure or magic item that you encounter or an embarrassing fact about an NPC. Mechanically: once per session you may astound your party’s condescending wizard by pulling this lore or rumor out of your petticoat or pantaloon by making a successful History check, generally with a lower-than-average DC (DMs discretion). Once this secret is rolled however, you lose this ability, but it can be rerolled to learn another secret. This can be rolled once per game session, and if you fail you don’t loose your secret.

6 It was very shiny and stuck out like a soup spoon… On a successful melee hit, you may use your bonus action to make a Sleight of Hand attempt to grab an item (other than the target’s weapon) off a target. This only works once per combat against anything above zombie-intelligence who sees it. Re-rolling this result means you add double your proficiency bonus to the roll. Rolling this a third time means you are, in fact, able to disarm your opponent, however they receive a Strength saving throw to oppose your Sleight of Hand check. After this it is a wasted roll.

7 Alice was not such a mouse as she used to be. +1 Dexterity, to a maximum of 20. Excess may go to Strength or Constitution.

8 The blue one certainly did make you taller, of that Alice was sure…You add double your proficiency bonus to identify the properties of drugs and plants with drug-like properties, generally making a Perception check to do so. Rolling this again means you can mimic the effects of one potion worth 50gp or less once per day if you have access to narcotics. Rolling this again is a wasted roll.

9 Jack could be very charming when he needed to be. Your silver tongue grants you double your proficiency bonus on Bluff checks. If you reroll this ability then once per day one person will automatically believe one (semi-plausible) lie you tell. Additional rolls grant you an additional lie per day, up to a maximum of four.

10 Alice knew to curtsy at times like this, and so she did. Despite the low company you keep, you’ve been working on your manners. Add double your proficiency bonus on Persuasion checks. Rerolling this result means members of the upper classes instinctively recognize you as one of their own. You have advantage when making Persuasion rolls against the aristocracy. Additional rolls of this result are wasted.

11 It was so lovely, and—according to the book—it was right there. The dress made of manticoreflesh, the house full of lilacs, the magical fishgutting knife—-whatever the thing that you always wanted is, it’s there. 4 sessions worth of adventure away or less. Tell your DM, who then must place it. Your DM is not, however, obligated to make it easy, and if you chose not to divert from your other obligations to pursue this quest then the chance is lost. Until you reroll this result, of course.

12 Alice had not known her mother’s cousin very well, and decided that it was a bad thing that she had died…You have been willed 5000 units of the local currency worth of random mundane (nonmagical) objects. Here’s how it works: you have exactly ten seconds real time to say what was left to you. You now have all that stuff, assuming it adds up to less than 5000gp. You do not get xp for this treasure.

13 They kept talking as though Jack was a rhododendron in a pot. Add double your proficiency to your Stealth. Rolling this again means you can deal a Sneak Attack as a Rouge of half your level (minimum 1d6 damage) if you are attacking from concealment, but only once per battle.

14 She knew from school what the word meant, but did not know if it was rude or not. The next time you encounter a written or spoken language you may attempt a History check. If successful you happen to know (and had simply forgotten) the language. Add it to the list of languages you know. Rerolling this allows you to ‘remember’ an additional language.

15 Alice quite liked drawing, and had an impressive box of crayons at home. You are adept at forgery. By making a Deception check and expending about 40gp in materials you can make a facsimile of one mundane item or document, assuming you’re familiar enough with the item. Attempting to create something to dupe someone without copying from something else (fake papers proclaiming your party’s paladin to be the newest member of the queen’s guard, for example) you are at Disadvantage for the roll.

16 He thought it might be a saltcellar, or at least that seemed like the right word for it. You can appraise treasure with surprising accuracy: you can estimate the value of nonmagical things flawlessly with an Investigation check, and if a piece of treasure is not what it seems on any level you will get an inkling. As in, you’ll go “Is this not what it seems?” and the DM will go “Yeah, you’ve seen a lot of jade urns in your day and this is not what it seems somehow—you’re not sure how.” You won’t know what it is, but you’ll sense that it is strange. If rolled a second time you may make Investigation checks to identify the properties of strange items, including magical items. Additional rolls of this result are wasted.

17 They all listened attentively as Alice told her tale. +1 to Charisma, to a maximum of 20. Excess goes to Wisdom or Intelligence.

18 They began to throw stones, and Jack began to avoid them. You gain Evasion, as the Rogue ability. Rolling this again is wasted.

19 She tried to remember what she knew about stoats. Add double your proficiency bonus to Handle Animal checks. If rolled a second time then there is a 1 in 6 chance that any animal you have successfully handled is in fact a magical talking animal, and appreciates your attentiveness. This can only happen once per game session, and it will help you in ways that would not significantly endanger it for the rest of the day. If you want to keep it in your company longer it will likely want something in return…

20 Alice was beginning to think such a strange life might suit her. Reroll twice on this table. If you roll 20 again you reroll again, but do not gain another bonus roll.

I do so apologize…

At level 2 you can easily trip any medium-sized, human-like creature that is otherwise engaged with someone or something else on a successful melee attack roll. This ability can only be used once per combat, as now your enemies know not to underestimate you, unless the DM decides the enemies are incapable of utilizing such reasoning (mindless zombies, etc). At level 3 and above this attack also deals damage, equal to your Charisma or Dexterity modifier (your choice) and the die shown below. An Alistair can become quite deadly using these ‘accidental’ attacks.

3rd: 1d4
5th: 1d6
7th: 1d8
9th: 1d10
11th: 1d12
13th: 2d8
15th: 1d20
19th: 2d20

Offensive Cretin

You’re starting to become adept at dueling. At 5th level choose a one-handed martial melee weapon you are proficient with; you now deal +2 damage with that weapon if you aren’t holding anything in your other hand. Additionally, you can challenge enemies to a duel with a Persuasion check. If successful they will be more than happy to grind a weakling like you into paste, but you are more than you seem. So long as no one assists you with the duel you score a critical against the enemy on a 19-20, and have +1 AC. If your friends are forced to save you however your confidence takes a blow, and you are no longer proficient with your dueling weapon and loose this ability until you take an extended rest.

Uncanny Eye

At level 6 for each combat round you spend just watching someone (i.e. you’re not doing anything except maybe moving and you are not being attacked yourself) you get +d10 to hit AND +d10 to damage OR +d10 to any attempt to trip, grab, or otherwise mess with the target when you finally do decide to attack per round spend observing them. This only works on targets that are engaged in combat while they are being observed. The ability can only be used once per battle, unless the enemies at hand are mindless or otherwise incapable of seeing the Alistair perform this attack. At level 10 raise the die used to d12, than a d20 at level 14.

Astonishing Attack

You are surprising. At level 7 you may add your entire Charisma score to your to-hit roll with any improvised weapon you picked up this round (who knew what you could do with a gingerbread man?). If you hit, add your entire Charisma score to the damage. This trick only works once per fight.

How many times could this kind of thing happen?

At level 11 you may escape death or another equally awful fate exactly once. You must spend at least a round playing possum to build tension but….surprise! You jumped out of the way just in time! If used you regain this ability at levels 15 and 19.

Unsavory Attack

Being in the company of rough and tumble adventurers has taught you that to win the day you must occasionally do unpleasant things. At level 14 you can use a garrote (or equivalent improvised weapon) to attack a creature who is engaged with someone else or otherwise not paying attention to you, and would logically be susceptible to strangulation. On a hit you automatically start a grapple, and so long as you maintain it the enemy suffers 1d8 damage+Dex modifier each round, and after three consecutive rounds must begin making Constitution saving throws or be rendered unconscious. Additionally when you drop caltrops, marbles, or improvised equivalent, the first creature to run across them automatically falls prone (assuming they have legs)

Somewhat Neglected

At level 15 if you choose to do nothing but evade on your turn you gain +2 to AC in addition to the normal effects of taking the Dodge action (enemies suffer disadvantage on attacks). Each attack that misses you is considered a fumble.

Stranger than Strange

Alice had seen so many unusual things lately, it had become usual. By 17th level you’ve seen and done so much that nothing phases you—you are immune to insanity or confusion in any form. Even mind-altering cosmic horrors from the far edge of the cosmos are, like, whatever. You still do fear. Fear is good. Fear keeps you alive. Additionally, any allies who can see you likewise get advantage on saving throws vs insanity or confusion, on account of your steady eye.

A Queen (King) Among Fools

At 20th level when you are Exasperated you may select any effect from the table, rather than rolling. Additionally, select four abilities from the Uncertain Destiny table that would not be wasted rolls. You gain these abilities.


I absolutely love this! There is definitely some balancing to address I think, but I really like it thematically. We can playtest it if (when) someone dies and chooses it, but I won’t be adding it to any of the “bonus” classes for Gilead. Thanks for the addition.

The Alistair

Glad you like it! Rereading there are abunch of errors, she’s supposed to use a d6 hit firdie for one. The general rhythm of the character in combat is to hold, hold, hold, then boom surprise someone with something nasty. Or spin the big roulette wheel of their other abilities and hope for the best

The Alistair

Also I agree this shouldn’t be something you can multiclass into

The Alistair

Next class posted will be the Summoner, and if y’all aren’t sick of these after that I was thinking Inquisitor. Or something really strange like the Xenotheurgist or Psion. Oh! Or I could revamp some of the super-powery 4th edition classes like the Warden, Seeker, Avenger, and Swordmage! Oh, oh! Or I could…!

This is kind of my favorite part of the hobby if you hadn’t noticed…

The Alistair
fignewtonfood sean_conner_52012

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