Fool

The tall lithe figure tumbles through the market square, springing from hand to foot. Their multicouloured coat and fitted leathers flashing in the noonday light. Their mask, a twisted grinning face in porcelain white. Their tumbles finish and the crowed applause, the figure bows, slips theatrically and tumbles again. The crowed roars with laughter and cheers not knowing their purses are a little lighter. 

A stout Fool, his mask locked in a veneer of a laughing man, tells jokes and spins satire in the kings court, mocking nobles, and dignitaries to the kings great pleasure. The nobles don't seem too pleased, but know to harm the kings fool is no laughing matter.

An orc chieftan swings his axe down at a motlyed jester. The jester ducks and weaves beneath the axe's blows, mocking the great warrior as he just misses the bells on her outragiously large hat. Each slash of her silver tounge breaks the spirit of the orc chieftan another crack. Her crying mask a grim reflection of his broken mind. When the time is right she sinks her dagger into his back and whispers one final twisted joke in his ear. 

Fools, Jesters, Harlequins, Jokers. These master entertainers take the arts of music, storytelling, magic and acrobatics to the streets and to seats of power. Those bards who take on the motley and the mask are few and far between, but they bring laughter and mockery in equal parts. The people of the streets love when the jester comes, juggling and singing, mocking the good folk with gentle savagery, turning a fall into a tumble into a performance of sparks and magic. They can spin a joke that tears down a nobleman, or mock a street urchin in a way that brightens even the darkest of days. The fool is welcome in the chambers of kings, in taverns, and street corners bringing hilarity in all its forms. The Fool in their motley and mask can be something other than human, something more. And when those trained in these ways are inclined, they may bring chaos unbridled and take everyone so unawares, that there is no chance to stop the havoc they shall wrought.

Skilled Street Performer

The road to becoming a Fool is filled with street performances of tumbling and skilled juggling and dexterous illusions. Should you perhaps steal a coin purse or two while making a copper appear and dissapear before the audiences eyes, while flipping across the square, well... you have to eat. When you take this subclass at 3rd level, you gain proficiency with the Acrobatics and Sleight of Hand skills.

Master of Mockery

Your job is to be quick witted, and sharp as an assassins blade. None can outcompete your carefully worded mockery, some even say it's magical how damaging a fools mockery can be. You learn the Vicious Mockery cantrip and Hideous Laughter spell , if you don't already know them, which don’t count against the number of bard spells you know. Whenever you use Vicious Mockery, you may do so as a bonus action. When a creature fails its saving throw against your Vicious Mockery by 5 or more, you deal additional damage equal to your bardic inspiration die.

Motley and Mask

The Fool is often seen wearing their charactersitic Motley coloured and carefully patched clothes, with the masks to hide their true intentions beneath veneers of laughing, crying or twisted expressions. While wearing your motley and mask, creatures have disadvantage on Wisdom (Insight) checks on you. Additionally, you may choose between one of three masked expressions which give bonus effects. You may don and/or doff one of these masks as a bonus action. 
Grinning: You gain advantage on Charisma (Persuasion) Checks.
Laughing: Creatures that can see you that you target with a spell which require a Wisdom, Intelligence, or Charisma Saving Throw reduce their saves by 1d4. 
Crying: Whenever you deal damage to a creature with a weapon attack you deal an additional 1d4 psychic damage.

Acrobatic Mobility

At 6th level, your acrobatic skills allow you to traverse places most cant and escape situations with unbelievable feats of dexterity. You gain the following uses of your bardic inspiration.

Acrobatic Movement
You may, as a bonus action, expend a bardic inspiration die to be able to dash. During this dash you can run along vertical serfaces, have a climb speed equal to your walking speed, and if you need to make a Dexterity (Acrobatics) check or a Dexterity Saving throw you may add your Bardic Inspiration die to the roll.

Spontaneous Performance
When you succeed on a Dexterity saving throw to take only half damage, you may expend a bardic inspiration die and make a Charisma (Performance) check as well against the same DC. If you succeed on the Performance check you instead take no damage, and all allies that can see you recieve bardic inspiration.

Tumbling Escape
When a creature targets you with an attack you can use your reaction to expend a bardic inspiration die and add the number rolled to your AC until the start of your next turn. You must also move at least 5ft + the number rolled on the die (rounded to the nearest 5) away from the creature, which you do without provoking opportunity attacks from that creature. If the attack misses as a result of this ability, grant one creature within 60ft of you bardic inspiration.

Unknowable Intentions

Starting at 14th level, while wearing one of your masks, no creature can read your intentions. You may, when your roll initiative, make a Charisma (Deception) Check. If your check roll is higher than a creatures passive insight that creature cannot use reactions against you. A creature may use its action to make a Wisdom (Insight) check against your deception check. If it succeeds it is immune to this ability for the next 24 hours.

Unparralelled Wordsmith

At 14th level, you are the pinnacle of using your words to twist the minds of your enemies.

Whenever you make a Charisma Check, you can treat a d20 roll of 9 or lower as a 10.

Additionally, whenever you cast a spell from the Enchantment or Illusion spell list which requires Verbal Components, you may do so as part of normal speech and creatures must make an Insight Check against your Spell DC to determine that you were the spells caster. Creatures that are hostile to you or your companions do not gain advantage on saving throws against spells cast in this way