Jester

Many assassins lie in the shadows before striking, some thieves move through the night like a shadow and some scouts move through the wilderness with an unmatched ease; but very few people can claim to have the showmanship and pizazz of Jesters. Rogues of this archetype don't just work in plain sight, they flourish in the spotlight, whether its to listen in on the dark dealings of nobles, to kill a target of high profile or to steal a priceless artifact these performers are experts at making a scene without becoming a suspect.

Slapstick Setup

When you choose this archetype at 3rd level, you dance around your foes, distracting them while your allies strike. When you miss a melee weapon attack roll on your turn, the next attack made against the target is made with advantage. If the attack hits, it gains a bonus to the damage equal to half your rogue level.

Hysterical Haste

Starting at 3rd level, your comical performance momentarily bewilders your foes, giving yourself a brief moment to act. You can give yourself a bonus to your initiative rolls equal to your Charisma modifier.

Additionally, you have advantage on Charisma (Deception or Performance) checks made to confuse or distract creatures.

Vexing Vengeance

At 9th level, you mock creatures as they strike you, terrifying them with your laughter. Once per turn, when a creature hits you with a melee weapon attack, the creature takes psychic damage equal to your Charisma modifier.

Topsy-Turvy Takedown

Starting at 13th level, you finally get to use your punchline. When a creature under the effect of your Slapstick Setup feature takes damage, you can use your reaction to make one melee weapon attack against the creature.

Satirical Slaughter

Beginning at 17th level, your acts of slaughter are so gruesome they cause your enemies to break mentally. When you reduce a creature to 0 hit points, creatures of your choice within 60 feet must succeed on a Wisdom saving throw (DC equal to 8 + your proficiency bonus + your Charisma modifier) or be stunned until the end of your next turn.

Once you use this feature, you can’t do so again until you finish a short rest.