Base Class: Bard
The Jester is one who oscilates between charging in for up close and personal strikes and hanging back to play some songs for more supportive purposes.
Multiple abilities focus on weaving in and out of positions as needed.
Bonus Proficiencies
When you join the College of Jest at 3rd level, you gain proficiency with all Light Melee Weapons.
Laughter's Inspiration
Also at 3rd level, you learn to inspire others to better face the stressful horrors of the world. A creature that has a Bardic Inspiration die from you can roll that die and add the number rolled to an initiative roll. Alternatively, they can expend the die without rolling it to take the Disengage Action as a Bonus Action, or remove one condition of Charmed, Frightened, or Paralyzed as a Bonus Action.
Setups and Punchlines
Starting at 6th level, you can use the Dash and Disengage Actions simultaneously as a single Bonus Action, and gain new tactics to use in combat
Dirk: When attacking using a Light Melee Weapon, you can move 10 feet closer to the target without using any movement before making the attack.
Harvest: When wielding two Light Melee Weapons that each deal either Slashing or Piercing damage, you can use your action to target a creature or two adjacent creatures within 5 feet of you and make them make Constitution Saving Throws against your Spell Save DC. If either fails, they take 1d4 damage of your choice of type between the damage types of your two weapons, and at the start of each of their next three turns they take 1d4 damage of the chosen weapon's type again.
Solo: Whether you play a mighty riff that pushes you forward on your knees or a joyful piece to put a spring in your step, you quickly pull your instrument and play a few notes to rush to your nearest foe, while preparing for retaliation. Up to twice per Short or Long Rest, you move up to 30 feet closer a hostile creature you can see, without using movement, as an action, and gain +1 AC per 10 feet moved as part of this action until the end of your next turn. Hostile creatures within 20 feet of you have Disadvantage to attack rolls for attacks that do not target you until the end of your next turn.
Slice Off: When wielding at least one weapon that deals Piercing or Slashing damage, you can use your action to make a target within 5 feet of you make a Constitution Saving Throw against your Spellsave DC. On failure, they take half of the weapon's normal damage (if wielding two that qualify, your choice of which) plus 1d6 damage of the weapon's damage type and take 1d6 damage of that type at the start of each of their next three turns.
The Grand Performance
At 14th level, you have woven your performance into your capacity for war. You have two new actions;
Battle Ballad: You spend a moment playing a tune befitting a still raging war. Allies within 30 feet of you, including yourself, gain a +1 to attack rolls and saving throws until the end of your turn after your next.
Finale: You put your all into a singular, powerful blow. Once per Short or Long Rest, you make one attack roll, with Advantage, against a foe within 40 feet, and the attack roll is a Critical Hit on 19 as well as on 20. On hit, the target takes Psychic damage equal to a number of d12s equal to your Charisma Modifier minus how many uses of Bardic Inspiration you still have left. You then must move as far from the target as possible, up to 30 feet. You do this without using movement. After using Finale, you have Disadvantage on all attack rolls and initiative rolls until you complete a Short or Long Rest.
Previous Versions
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