College of Jesters: Bard

These Bards are students of comedy who live for the sound of laughter. However, for the College of Jesters, humour is much more than entertainment. For them, the absurdity of existence is itself a divine force, and comedy is sublime. Members of the College of Jesters are often dismissed as fools, but that is how they like it, so that they make can fools of others. These Bards often dress in motley clothes and many wear make-up, at least when they perform.

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Bonus Spells
When you join the College of Jesters at 3rd level, you gain the vicious mockery cantrip if you don't already know it. Also, you learn the hideous laughter spell, if you didn't know it before, and you can cast it without expending a spell slot once per day.

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Cutting Jest
Also at 3rd level, you learn how to use your jests to distract, confuse, and otherwise sap the confidence and competence of others. When a creature that you can see within 60 feet of you makes an attack roll, an ability check, or a damage roll, you can use your reaction to expend one of your uses of Bardic Inspiration, rolling a Bardic Inspiration die and subtracting the number rolled from the creature’s roll.
You can choose to use this feature after the creature makes its roll, but before the DM determines whether the attack roll or ability check succeeds or fails, or before the creature deals its damage. The creature is immune if it’s immune to being charmed, however it need not be able to hear you, since Bards from the College of Jesters are also practiced mimes, and they can also use their faces and their physicality alone to create effective jests.

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Cutting Deeper
At 6th level, your observation of others gives you insight into their foibles and insecurities and makes you even more adept at sapping their confidence with your humor. If you have spent at least one round observing someone you can use Cutting Jest to greater effect. If the target's ability check or attack roll fails after you have used Cutting Jest, then you may opt for them to suffer from psychic damage. Roll another Bardic Inspiration die, and this represents psychic damage to the target.

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Fool's Luck
At 14th level, your failures sometimes miraculously turn into success in unexpected ways. For example, you might miss on an attack roll, but instead hit a shelf which causes something to fall off and hit your opponent. Any time you roll a 1 on an attack roll, ability check or saving throw, you may immediately reroll. You may use this feature once and must finish a long rest before using it again.