Harlequin

As an archetypal Harlequin, you excel at distraction. You rely on your charming (or some would say overbearing) personality to win over allies and unsettle enemies.

 

Based on Warlock Homebrew's Jester subclass.

Harlequin’s Mask

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and two of the following: Acrobatics, Performance, or one kind of gaming set.
As an object interaction you can either don a mask in your possession with traditional harlequin markings. While wearing your Harlequin’s Mask you have advantage on any check made to cause a distraction.

As a reaction when a creature you see misses with an attack, you can insult them. The target must succeed on a Wisdom saving throw with a DC equal to your 8 + your proficiency bonus + charisma ability modifier or have disadvantage on the next attack roll it makes before the end of its next turn.

Acrobatics

You gain proficiency in Acrobatics

Gaming set

You gain proficiency in one kind of gaming set

Performance

You gain proficiency in Performance

Juggler

You can use small items such as tankard, fork, cards, and other as a weapon with finesse and thrown property dealing 1d6 + your dexterity modifier damage on a ranged attack.

The damage die increases to d8 at level 9 and d10 at level 13.

Wyrd Theatrics

When you don your mask, you can choose to cast Disguise Self.

You can use this feature number of times equal to you 1 + charisma ability modifier. The uses of this feature reset after you take a short or long rest.

Tumbling Fool

At 9th level, every time you use the Disengage action (including with your Cunning Action feature), add 10 feet to your movement speed until the end of your turn.

Cruel Comedy

Starting at 13th level, whenever a creature fails its save against the Wisdom saving throw imposed by your Harlequin’s Mask feature, the first attack you make against that enemy before the end of your next turn has advantage.
In addition, while wearing your Harlequin’s Mask you are immune to being charmed.

Last Trick

Starting at 17th level, when you are reduced to 0 hit points and are not killed outright, you can choose to drop to 1 hit point instead and place yourself under the effects of a false death identical to the feign death. On your turn you can end this effect with no additional action.
When you end this effect, you have advantage on any attack that targets a creature which believed you were dead, until the end of your next turn. Additionally, the first attack you make that hits such a creature before the end of your next turn automatically benefits from your Sneak Attack feature, and deals an extra 4d6 damage of your weapon’s type.
Once you use this ability, you can’t use it again until you finish a long rest.