Jester (5e Class)

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For as long as time can remember, every king has had one, or several, Court Fools to aid him in entertainment, and mention issues that are too hot to allude too without making them a joke. Not only were they used as pieces of performance, but also as a hidden ally to the King. At birth, they're trained in items such as instruments and knives, actions such as dancing and striking, and perseverance like no other. Despite their harsh treatment, name calling, sullying, and straight abuse, they are very proficient and very lethal assassins. Jesters (Court Fools), tend to purposefully do silly and rather dumb things to try and attract the idea of them being a defenseless, useless, and harmless patron. They are trained to speak in lies and charm the crowd with their speech pattern. A proper Jester can talk his way out of many things, and into many things. They have the ability to lie on the fly and do anything it takes to hide the truth without falter in their words.

Creating a Jester[edit]

Ever wanted to play the 'Fool'? Need an assassin class that's a little more eccentric? Need to use your mad charm to 'peacefully' make your way through? Do you want to boost your teams morale? You should focus on Dexterity, Charisma, and Wisdom.

Quick Build

You can make a Jester quickly by following these suggestions. First, Dexterity should be your highest ability score, followed by Charisma. Second, choose the Entertainer background. Third, choose the rapier and entertainment pack items.

Class Features

As a Jester you gain the following class features.

Hit Points

Hit Dice: 1d10 per Jester level
Hit Points at 1st Level: 10 + Constitution modifier
Hit Points at Higher Levels: 1d10 (or 6) + Constitution modifier per Jester level after 1st


Armor: None
Weapons: Simple weapons, Martial weapons, finesse Weapons
Tools: Thieves' tools
Saving Throws: Dexterity and Charisma
Skills: You have insight, perception, performance and 1 of: Acrobatics, Deception, History, Intimidation, Persuasion, Sleight of Hand, Stealth.


You start with the following equipment, in addition to the equipment granted by your background:

  • (a) Shortsword or (b) Rapier
  • (a) an Entertainer's Pack or (b) an Explorer’s pack
  • two daggers, and thieves' tools
  • Jester's Outfit (design of your choosing; must include mask)

Table: The Jester

Level Proficiency
Cantrips Known Features Spells Known —Spell Slots per Spell Level—
1st 2nd 3rd 4th 5th 6th 7th 8th 9th
1st +2 2 Jester Garb, Cantrips, Sharp Tongue 0 2
2nd +2 2 Expertise, Weightless 0 3
3rd +2 2 Spellcasting, Magical Secrets 5 4 2
4th +2 2 Ability Score Improvement, War Magic 5 4 3
5th +3 3 Improved Critical, Extra Attack 5 4 3 2
6th +3 3 The Fool's Card, Expertise 5 4 3 3
7th +3 3 6 4 3 3 1
8th +3 3 Ability Score Improvement 6 4 3 3 2
9th +4 3 Death's Dealer, Superior Critical 8 4 3 3 3 1
10th +4 4 Shadow Dance 8 4 3 3 3 2
11th +4 4 8 4 3 3 3 2 1
12th +4 4 Ability Score Improvement 10 4 3 3 3 2 1
13th +5 4 12 4 3 3 3 2 1 1
14th +5 4 Creeping Shadow, Toy Mask 12 4 3 3 3 2 1 1
15th +5 5 Laughing Jack, Flash Step 14 4 3 3 3 2 1 1 1
16th +5 5 Ability Score Improvement 14 4 3 3 3 2 1 1 1
17th +6 5 Demon's Favor, God's Betrayal 16 4 3 3 3 2 1 1 1 1
18th +6 5 16 4 3 3 3 3 1 1 1 1
19th +6 5 Ability Score Improvement 18 4 3 3 3 3 2 1 1 1
20th +6 5 Unveil The Once Hidden 19 4 3 3 3 3 2 2 1 1

Jester Garb[edit]

You have been around your fair share of royals their magical associates, along the way you learned to imbue magical energy into your attire: Beginning at 1st level, while you are wearing no armor and not wielding a shield, your AC equals 10 + your Dexterity modifier + your Charisma modifier.


At 1st level, you know two Jester cantrips (which are any cantrips from the bard spell list and/or warlock spell list) of your choice. You learn additional Jester cantrips of your choice at higher levels, as shown in the Cantrips Known column of the Jester table.


At 2nd level, choose two of your skill Proficiencies, or one of your skill Proficiencies and your proficiency with Thieves' Tools. Your Proficiency Bonus is doubled for any ability check you make that uses either of the chosen Proficiencies. At 6th level, you can choose two more of your Proficiencies (in Skills or with thieves' tools) to gain this benefit.

Sharp Tongue[edit]

At 1st level, you've trained your manner of speech since you were a child. You can only choose one and you cannot change it afterwards.

Voluntary Liar

Since a child, you were taught to lie. You were taught to keep a straight face and a sincere voice, even in the face of a lie. You gain proficiency to Deception checks.

Charm of the Tongue

Since birth, you've been born with an unexplained talent to persuade people to do your bidding, or to make them vote in favor of you. You gain proficiency to Persuasion checks.

Masked Predator

As a child, you were gifted a mask that you would wear for all your life. No one has seen under it, and you're not even sure of what you look like. Since this is such a largely known fact for Court Fools, many fear the unknown. You gain proficiency to Intimidation speech checks.


At the beginning of level 2, the Jester can use their DEX modifier instead of their STR for athletic checks.


By 3rd level, you have learned to draw on your music professionalism and performance to cast spells.

Spell Slots

The Jester table shows how many Spell Slots you have to cast your Spells of 1st level and higher. To cast one of these Spells, you must expend a slot of the spell's level or higher. You regain all expended Spell Slots when you finish a Long Rest.

Spells Known of 1st Level and Higher

You know two 1st-level spells from the Jester Spell List (which includes any spells from the bard and warlock spell lists) of your choice.

You learn an additional jester spell of your choice as shown in the Spells Known column of The Jester table.* Each of these Spells must be of a level for which you have Spell Slots. For instance, when you reach 7th level in this class, you can learn a new spell of 1st or 2nd level.

Additionally, when you gain a level in this class, you can choose one of the Spells you know and replace it with another spell from the Jester spell list, which also must be of a level for which you have Spell Slots.

(* Table lacking information or otherwise formatted incorrectly. Until this can be remedied, use bard or warlock table or wing it.)

Spellcasting Ability

Charisma is your spellcasting ability for your Jester spells, since their power derives from the charm of your performances. You use your Charisma whenever a spell refers to your spellcasting ability. In addition, you use your Charisma modifier when setting the saving throw DC for a Jester spell you cast and when making an attack roll with one.

Spell save DC = 8 + your proficiency bonus + your Charisma

Spell attack modifier = your proficiency bonus + your Charisma

Spellcasting Focus

Jester Mask:to activate a spell you must touch your mask you may use that as your arcane focus.

Magical secrets[edit]

You have been around. Often spying for royal families and even the royals themselves. Here and there you've picked up some of their talents and adapted them as your own.

At 3rd level, you have plundered magical knowledge from a wide spectrum of disciplines. Choose two Spells from any class, including this one. A spell you choose must be of a level you can cast, as shown on the Jester table, or a cantrip.

The chosen Spells count as Jester Spells for you and are included in the number in the Spells Known column of the Jester table.

You learn two additional Spells from any class at 13th level and again at 19th level.

Ability Score Increase[edit]

When you reach 4th level, and again at 8th, 12th, 16th and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

War Magic[edit]

Beginning at 4th level, when you use your action to cast a cantrip, you can make one weapon attack as a bonus action.

Improved Critical[edit]

You may pretend about a lot of things. But how hard you hit is not one of them. At 5th level Your weapon attacks score a critical hit on a roll of 19 or 20.

Extra Attack[edit]

Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn.

The Fool's Card[edit]

At the beginning of level 6, the Jester is now able to use illusionary magic. The Jester may create 1 "Fool's" card every short or long rest. They may only have up to three of these cards at only one time. As a Reaction the Jester can conjure "The Fool's" card at any given moment. With this card, they are able to dodge, or parry any singular attack.


The jester gains advantage on saving throws associated with a single magical attack, in addition if the jester makes a saving throw that would allow them to take half damage they take none.


The jester can Parry a single melee attack. This ability allows the jester to roll 1D20+ Dexterity modifier if the outcome is at least half of the the attack roll of the enemy the jester parrys the attack negating it.

Death's Dealer[edit]

At the beginning of level 9, the Jester has the ability to summon strength through the Tarot Cards. The Jester can only wield (your Charisma modifier + half your proficiency bonus) cards before having to complete a long rest, not including "The Fool". Once he chooses either the Light or Dark Tarot Cards, he can only summon from that deck selection for the day, "The Fool" not included. From the light deck he may choose which card he summons. From the dark deck he chooses the card summoned at random, rolling 1d10 to decide.

Light Deck[edit]

The Magician
The jester can conjure 1 magical weapon of his choice that lasts for the next hour.
The High Priestess
The Jester can use his bonus action to cast healing word on a creature.
The Empress
The Jester gets a +2 to all saving throws for the next 4d6 minutes.
The Emperor
If the Jester drops below one hit point, he may make a single reaction against the enemy that targeted him.
The Hierophant
The Jester gains a +3 on their next Stealth or Insight check.
The Lovers
When one ally is struck within 30 feet of the jester by a hit that causes their hit points to drop to 0 or lower, the jester may swap hit points with their ally.
The Chariot
The Jester gains the ability to knock a single enemy within 30 ft of them unconscious for one minute. The target must roll a DC WIS save of 8 + half Jester's level. If they succeed the save, they do not fall unconscious. They can roll another save at the beginning of their turn to try to regain consciousness early.
The Jester can use this card to double the damage dealt after the attack hits in exchange for rendering both arms unusable for 30 seconds.
The Hermit
The Jester gains the ability to telepathically relay information to everyone he considers allies for 5 minutes.
When the jester is attacked he can halve the damage that would be dealt to him, dealing the other half to his opponent as a reaction.

Dark Deck[edit]

1. The Thief
The jester can turn invisible if they are in dim-light or darkness for the next 5 rounds.
2. The Watcher
For the next 5 minutes you can see through magical and non-magical darkness.
3. The Moon
When you cast this card all lights within 120ft are snuffed out; magic lights are snuffed out for 10min and non-magic lights are snuffed out forever.
4. The Hanged Man
The Jester is able to restrain a single target with magical rope. The target must role a DEX saveing throw with a DC of 8 + half Jester's level rounded down + DEX mod. If they succeed the Save, they are only restraint. If they fail the save, the Jester can choose to whether or not hang the target by their neck, dealing 1d8 damage per turn until the target is released by an outside force.
5. Death
The Jester marks this enemy for death, dealing 1d12 necrotic damage to the enemy. Additionally, if the target's hit points fall to 0 within 3 rounds of being afflicted by this card they die instantly. If this effect is activated the jester chooses one ally or himself to fall to -1 HP.
6. Temperance
The Jester is able to take the damage of an enemy in turn sequences evenly divisible by the damage to the lowest number of rounds possible. E.G, if an enemy deals 12 damage to the Jester, he is able to take 6 damage one turn and then 6 damage his next turn AFTER he finishes his actions.
7. The Tower
The Jester is able to destroy any weapon within 20 ft from him that is not being held by a creature and that is not magical.
8. The Star
The Jester may force succeed a saving throw made by one ally at the expense of receiving the effect of a failed saving throw themselves.
9. The Sun
The Jester can instantly negate all negative mind effects afflicting him or a single creature they can see.
10. Judgement
The Jester is able to revive a single ally within 60 ft of them from death the round that they fail their last death saving throw, but at the cost of knocking the jester unconscious for 1d8 rounds.

Savage Spells[edit]

At the beginning of level 9, you learn how to make your weapon strikes undercut a creature's resistance to your spells. When you hit a creature with a weapon attack, that creature has disadvantage on the next saving throw it makes against a spell you cast before the end of your next turn

Shadow Dance[edit]

Beginning at level 10, as a bonus action, the Jester can swap locations with an ally. If any ally is within 50 ft of the Jester and if they are being attacked, as a reaction the Jester is able to swap places via netherswap with said ally, the jester may then and they may then roll 1d20 adding their Dexterity modifier. If the roll equals one half or more of the attackers attack roll, the Jester may take no damage from the attack. If less than half the Jester takes half damage.

The attack part of this feature can be used a number of times equal to your Charisma modifier (a minimum of once). You regain any expended uses when you finish a Long Rest

Creeping Shadow[edit]

Once the Jester reaches level 14, the Jester gains the ability to control the shadows of others. If a humanoid within 60 ft. of the Jester casts a shadow that the jester can see the jester can attempt to take control of their shadow. The target must make a Wisdom saving throw against the Jester's spell save DC; if the target fails then the Jester is able to take control over the enemy as if they were his puppet. This effect lasts for 30 seconds or until the Jester cancels this effect. While this is active, the Jester cannot move from his spot and cannot defend himself. The creature can roll a Wisdom saving throw at the start of their turn to break free early. This ability can be used once per long rest.

Toy Mask[edit]

At the beginning of level 14, the Jester's conjuration magic grows in strength. The Jester is now able to wear two layers on his mask. The first layer is his real mask and the second layer is a mask conjured as a weapon. The Jester is able to remove this mask and throw it as an explosive upon impact. This acts as the same as shooting an arrow from a bow or a weapon with the thrown property. The range of the throw is 10/60 and deals 4d6 force damage. The critical range for this attack is 18-20. Further, if the Jester is successfully grappling an enemy or sneaks up to an unsuspecting enemy, he can instead force the target creature to wear the mask. The target must make a contested Dexterity saving throw against the Jester's acrobatics check or take 3d8 psychic damage. The Jester must take a long rest before conjuring another "mask".

Laughing Jack[edit]

Once the Jester hits level 15, the Jester gets a jack in the box. They may use their action to crank it, it begins to laugh hysterically and uncontrollably during combat. Each hostile creature within a 60 ft. radius of the Jack in the box must make a Wisdom saving throw against the Jester's spell save DC. Enemies who fail the save are now frightened by the Jester. At the beginning of their next turn the Jester's box pops, anyone who is frightened by the Jester and can see the jack in a box takes 5d8 psychic damage.

Flash Step[edit]

At the beginning of level 15, the Jester is able to hasten his movement. As a bonus action, the Jester is able to quickly move. If he is next to an enemy when he uses flash step it does not target opportunity attacks. When jester is not next to an enemy and he uses flash step his movement is doubled. After using Flash Step a number of times equal to their proficiency bonus, the jester may not use it again until they complete a short or long rest.

Demon's Favor, God's Betrayal[edit]

At the beginning of level 17, The jester can call upon the ultimate power of chaos. When he fails his last death save he is dead for 4d6 rounds, then revives with 4d4 hit points with a new hit point maximum of half of his original hit point maximum. Additionally, he suffers from one of the following curses.


The Jester must randomly select one permanent affect his revival, using 1d10.

1. Desecration
The Jester gains level 1 exhaustion upon entering holy sites, I.E Temples, Monasteries, Churches, etc. The player can choose this condition up to 4 more times, all the way up to level 5 exhaustion.
2. Corruption
The Jester can no longer be healed by medicinal or magical means. They can only be healed by necrotic damage from an outside source.
3. Light's Shadow
The Jester gains the 'frightened' condition upon seeing holy/divine/celestial entities. Further, if the Jester is within 20 ft. of this entity, the Jester is compelled to attack this creature.
4. Taste of Blood
After every 4 hours, the Jester must intake half a liter of blood. If he does not, then the Jester attacks any creature near him until he sedates his thirst. If he does not consume any in 8 hours, the Jester dies.
5. Masochist
The Jester is compelled to inflict damage upon themselves. every 4 hour the jester must inflict 1d12 damage to themselves by any means available.
6. Weakened
The Jester deals half damage on attack rolls.
7. Insomnia
The Jester cannot sleep willingly. Each time he does, his mind is filled with the screams of the damned and he takes a 1d12 damage every hour he is asleep. However, if the Jester is forced asleep he will not be subject to this effect.
8. Burned
The Jester can no longer expose any skin, except hair, to the sun. If he does, the Jester takes 1d12 damage for every minute he is exposed to the sun. Any other light source, such as fire from a torch will not activate this effect.
9. Fragile Minded
The Jester has disadvantage on all Wisdom saves.
10. Remembrance
The Jester remembers how they die, what weapon was used, and where the final blow was struck. Because of this, the Jester takes immediate damage whenever said weapon comes into their line of sight. I.E if the weapon dealt 1d6, the Jester would take 1d6 immediately. Whenever the enemy strikes the Jester with the same weapon type that killed him at the same spot where he was last struck, the Jester takes double damage, triple against critical strikes. If they did not die by a weapon, but by a magical spell, the Jester cannot make any saving throws associated with the spell. If it was neither a spell nor weapon, but a creature, the Jester has disadvantage on attack rolls and deals half damage against said creature type.

After a feature has been used once, it can never be used again.

Unveil The Once Hidden[edit]

At the beginning of level 20, the Jester may remove his mask once every day. The Jester shows the creatures around him a darkness they've never encountered before, causing all creatures within a line of sight of him to make a Wisdom saving throw against the Jester's spell save DC. If they fail, the creatures become paralyzed until the mask is put back on. The Jester can maintain this form for only 1 minutes before he starts to become physically pained and morphed. For every turn after the 1 minute mark, the Jester takes 2d20 damage and his AC is reduced to 0. If the Jester does this to any fiend they, without doing a DC Save, are immediately under his command until the mask is put back on. Commands to these fiends are issued as a bonus action. If he does this within the vicinity of a celestial, they are obligated to attack the Jester without remorse. The Jester's mask becomes a legendary object, making it immune to stealing, shattering, or displacements. Once while the mask is off he can use one of any of the three legendary actions.

Legendary Actions[edit]

Demon's Legion
The Jester is able to summon up to 3 different Fiends (Demon). Each Fiend may only attack 3 times before dispelling itself, or until combat is over.
Inject the Mist
The Jester swipes his hand in front of him, creating a mist in a 40ft radius sphere that lasts for 1d12 rounds and deals 1d20 for each creature inside the mist, I.E. if there are 4 creatures inside the mist, it will deal 4d20 to each individual creature. They cannot make a save against this if the Jester has his mask off. This mist affects allies and enemies alike. Every round the jester can use a bonus action to move the mist 20ft in any direction.
Soul Surgery
The Jester can choose up to three creatures and remove their 'soul'. These creatures must make a Constitution saving throw against the Jester's spell save DC. If they succeed, they only take half damage. If they fail, each creature takes 6d12 damage, which is then distributed to the Jester's allies to heal them for an equal amount of Hit Points that was dealt to the creature(s).


Prerequisites. To qualify for multiclassing into the Jester class, you must meet these prerequisites: Dexterity 13 and Charisma 13.

Proficiencies. When you multiclass into the Jester class, you gain the following proficiencies: Two player-created daggers.

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