Scarring Mockery
Beginning at 3rd level, the Jester knows the true power of one's sense of self-worth. As such their mockery is deep cutting and destructive.
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.
Gallows Humor
Beginning at 3rd level, whenever you take damage from an attack roll, you can choose to mock yourself, adding 1d8 psychic damage to the damage roll. If you do, you can heal an ally within 30 feet for the total damage you take from the attack. This can be used a number of times equal to your Charisma modifier (minimum of once) and replenishes on a short or long rest.
Taunting Mockery
At 6th level, 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.
Last Laugh
At 14th level, 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.
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