Jester

For as long as time can remember, every king has had one, or several, Court Fools to aid him in entertainment. 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.

Scarring Mockery

3rd-level Jester feature

The Vicious Mockery cantrip is empowered for you. The base damage die of the Vicious Mockery cantrip is now 1d8 and all scaling uses this die as well. This mockery can be empowered further by expending one use of your Bardic Inspiration to roll the die and add the number rolled as extra damage to the cantrip.

Unsettling Words

3rd-level Jester feature

You can spin words laced with magic that unsettle a creature and cause it to doubt itself. As a bonus action, you can expend one use of your Bardic Inspiration and choose one creature you can see within 60 feet of you. Roll the Bardic Inspiration die. The creature must subtract the number rolled from the next saving throw it makes before the start of your next turn.

Taunting Mockery

6th-level Jester feature

Whenever an enemy fails a saving throw against your Vicious Mockery cantrip, if that enemy's next attack before the end of its next turn is against an ally instead of you, it must make a saving throw against the Vicious Mockery cantrip again. If it fails, the target's attack deals half damage.

Infectious Inspiration

14th-level Jester feature

Whenever you are reduced to 0 hit points by an enemy, you can laugh as loud as you are able and expend all of your remaining uses of Bardic Inspiration. Roll the dice and add them together. If you have no Bardic Inspiration uses remaining, you can roll a number of d8s equal to your Charisma modifier instead. Whatever the total number is, it is added to the next damage roll for all of your allies that can see and hear you. If the enemy that defeated you is themselves defeated within 1 round of you using this ability, you are healed for an amount of hit points equal to the total rolled. Once you use this feature, you cannot use it again until you finish a long rest.