Jester
A particular class of roguish entertainer, jesters use costumes, slapstick, and pranks to entertain and enthrall their audiences. On the battlefield, these nimble performers always have a dirty trick or two up their sleeves.
Variant Rule: Tumble
This archetype assumes the use of the optional "Tumble" action from the Dungeon Master's Guide:
Tumble. A creature can try to tumble through a hostile creature’s space, ducking and weaving past the opponent. As an action or a bonus action, the tumbler makes a Dexterity (Acrobatics) check contested by the hostile creature’s Dexterity (Acrobatics) check. If the tumbler wins the contest, it can move through the hostile creature’s space once this turn.
Gregarious Performer
3rd-level Jester feature
You gain proficiency in the Performance skill if you don't already have it. You also gain proficiency with the disguise kit. Your proficiency bonus is doubled for any ability check you make that uses these proficiencies.
Tumbling Acrobat
3rd-level Jester feature
If you've tumbled through a creature's space this turn, your movement doesn't provoke opportunity attacks from that creature until the end of the turn.
You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you've tumbled through its space this turn and you don't have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.
Bag of Tricks
9th-level Jester feature
When you tumble through a creature's space, you can choose one of the following effects. The save DC for these effects equals 8 + your Dexterity modifier + your proficiency bonus.
Cheap Shot. You take advantage of the creature's vulnerability. The creature must succeed on a Constitution saving throw or be stunned until the start of your next turn.
Pie in the Face. You attempt to slam a pie into the creature's face. The creature must make a Dexterity saving throw. On a failed save, the creature is blinded until it takes an action to scrape the pie off.
Shoelace Tie. You attempt to bind the creature's feet together. The creature must make a Strength saving throw or fall prone and be unable to stand up until it uses an action to disentangle itself.
Clowning Around
13th-level Jester feature
As an action, you can start a comedy routine that lasts for one minute or until your concentration ends (as if you were concentrating on a spell). When you do, choose a number of creatures within 60 feet of you that can see or hear you, up to your Charisma modifier (minimum of one). The chosen creatures must make a Wisdom saving throw (DC = 8 + your Charisma modifier + your proficiency bonus). On a failed save, for the duration of your routine, the creature has disadvantage on Wisdom (Perception) checks made to perceive any creature other than you, and it has disadvantage on attack rolls against creatures other than you. The effect ends on a creature if it can neither see nor hear you or if you attack it or cast a spell on it.
As an action, you can choose to end your routine early and cast Tasha's hideous laughter on one creature that is affected by this feature, with a save DC equal to 8 + your Charisma modifier + your proficiency bonus. The creature automatically fails its first saving throw against Tasha's hideous laughter.
Once you've used this feature, you can't use it again until you finish a short or long rest.
Roll with the Punches
17th-level Jester feature
You've learned to play off your injuries humorously, entertaining others at your own expense. When you use your Uncanny Dodge feature, you can force one creature within 60 feet of you that can see or hear you to succeed on a Wisdom saving throw (DC = 8 + your Charisma modifier + your proficiency bonus) or be charmed until the end of your next turn. While charmed in this way, the creature has disadvantage on its Dexterity (Acrobatics) checks to contest your tumbling and on its saving throws against your Bag of Tricks and Clowning Around features.
This subclass was created by u/I_am_Grogu_ for u/Traynfreek.