Path of the Fool

"I don't even know, man. This dainty half-elf dude entered the arena, drunk and dragging his sword on the ground, and we all started laughing, yeah? I mean, this washed-up ******* just shows up from nowhere and demands to fight the Champion, a seven-foot-tall behemoth of a man that once broke a man's spine with a punch! It shouldn't have lasted even half a second! But some-*******-how, the dude just stumbled around each of the Champion's strikes, landed the dumbest blows possible – ****er outright tripped and fell on top of the Champion, nearly cut his arm off –, and out of absolutely nowhere, chopped his head off in one swipe! Then, then he just slipped away immediately afterwards as we all looked, dumbfounded. No one has seen the bastard since. What the hell, man." – Graka, half-orc bookie.

Not all fools are created equal. Many spend their lives doing nothing of note, living ordinary lives and dying ordinary deaths. Some try to make something out of their lot, taking up arms in search for glory, and inevitably find their end in the jaws of wolves or at the bottom of particularly deep holes.

A few, however, seem to be blessed by fate.

Be it through sheer dumb luck, bizarre actions that completely dumbfound their enemies, or extremely clever ruses that can trick even the greatest masters, some exceptional fools can stumble their way into legend, inspiring many with their poorly calculated and entirely telegraphed sword strikes.

Bumbling Strike

At 3rd level, you think up this really cool move that you just gotta try.

You unleash a completely telegraphed, entirely avoidable attack. Once per turn, you can choose to make an attack with disadvantage. If the attack connects, it gains a damage bonus equal to half the sum of your Charisma modifier and your Proficiency bonus, rounded down.

Sticks and Stones

By your 3rd level, you have insulted plenty of strong people throughout your life, and you know how to hit them where it hurts.

You gain access to the cantrip Vicious Mockery.

Drunk Fool

Starting at 7th level, your experiences adventuring have led you to drink. Luckily, enemies seem to take you less seriously when you are drunkenly stumbling around in the battlefield. 

Whenever the chaos of battle becomes too much, you can use a bonus action and whatever booze you have with you to become inebriated. You gain the poisoned condition for one minute. While poisoned as a result of this bonus action, you gain a bonus to your AC equal to half of your Charisma modifier rounded down, and if an enemy misses an attack against you, your next attack against them is not made with disadvantage.

Oh, a Coin!

Alright, you are 10th level now, gotta take things seriously. Oh no, that big dude with a sword is charging straight at you! Better try and– ohhh, is that a gold coin on the ground?

As a reaction, you can impose disadvantage on one attack roll made by a hostile creature against you.

Tripping Blow

At 15th level, you have gotten better at putting your weight behind your blows. Though perhaps a bit too much.

Once per turn, you can choose to turn one of your attacks into a Tripping Blow if you moved at least 5ft towards the target immediately before taking the Attack action. If the attack hits, it gains a damage bonus equal to two times your Charisma modifier. Afterwards, you fall prone, and your turn immediately ends.

There Goes the Head

At 18th level, you have totally learned how to destroy a guy's head in one hit. No, really, you can!

When you roll a 20 on an attack roll against a creature that has at least one head and does not have legendary actions, before dealing damage, roll another 1d20. On a natural 20, you destroy one of the creature's heads, and the creature dies if it can't survive without the lost head. Otherwise, the creature suffers critical damage as normal with an extra damage bonus of two times your Charisma modifier.