Base Class: Bard
The College of Harlequins is for those who love to make others laugh. There are a wide variety of ways to make someone laugh--wordplay, long and winding story jokes, quick ripostes, slapstick, acrobatic acts, and so many more. Most come to this college by way of a deep-seated desire to simply bring happiness to the world, one chuckle at a time. Some people may find them irritating, but they know how to deal with hecklers. Some Harlequins go where the wind takes them, spreading as much laughter as they can, while some act as jesters for specific people or work a specific tavern.
Harlequins are known for dressing in outlandish outfits, often accompanied by face paint. This is not a requirement, as some may prefer to keep a low profile for their own reasons, but many revel in dressing in bright colors and silly clothes. What's most important is that they have the heart of a comedian.
Work the Crowd
When you join the College of Harlequins at 3rd level, you gain proficiency in Acrobatics and Performance.
Make 'Em Laugh
Also at 3rd level, you can spend one use of your Bardic Inspiration to tell a joke to one creature within 30 feet. The creature must roll a Wisdom save. If it fails, the creature laughs so hard it becomes incapacitated for one turn. The creature is immune if it can't hear you or if it's immune to being incapacitated.
The Perfect Roast
At 6th level, you can roast one creature alive, semi-literally. As an action, choose one creature within 30 feet. That creature must make a Charisma saving throw against your spell DC. On a failure, the creature is so affected by your joke, it takes 1d6 bonus damage for three turns at the end of its turn. You choose if the damage type is fire or psychic. On a success, the creature is unaffected. It automatically succeeds if it doesn't share a language with you or if it can't hear you.
Dedicated To The Bit
Starting at 14th level, when you make an ability check, you can expend one use of Bardic Inspiration to enthrall a crowd. Select up to five creatures within 60 feet. They must each make a Charisma saving throw against your spell save DC. Those that fail are enchanted by your performance and will obey your commands because they find you so charming and entertaining. They won't fight for you or risk their lives, but they will do nearly anything else in order to seem like your biggest fans. Creatures that succeed on the saving throw do not find you very funny. The save automatically succeeds if it doesn't share a language with you or if it can't hear you.