Bard
Base Class: Bard

Those who commit their minds and bodies to the college of failure tend not to take themselves that seriously. 

Inspiring mistakes

From 3rd level, your failures aren't really all that bad, and your creativity can itself be an inspiration. 

When you fail a skill check with a DC of 15 or less, or succeed on a skill check of 20 or more, you may give one bardic inspiration to an ally who can see you. Inspiration given out in this way do not count towards the total number you can give out per long rest.

You can use this feature a number of times equal to your Charisma modifier (minimum 1), regaining uses on a short rest. 

On ones behind

From 6th level a cloak of failure can protect you from the worst blows. All attacks have disadvantage on you while you are prone. When a creature misses you with an attack while you are prone the next attack against them has advantage. 

When they're down

You have advantage on all attacks against prone creatures

Mixed Results

From 14th level, sometimes, failure is the aim. 

When any creature within 60 feet of you makes an attack roll, ability check, or saving throw, you can use your reaction to expend two uses of bardic inspiration to reverse the outcome of that roll. The roll occurs as normal along with any modifiers that would normally occur, except the outcome is changed; a failure or miss becomes a success or hit, a success or hit becomes a failure or miss. For example, if the DC on an ability check is 20, and, after modifiers, your roll is 18, this would count as a success. If, after modifiers, your roll was a 22, this would be a failure. 

You must decide to use this before you roll.  You can use this feature once per long rest. 

You may not use this feature to influence the outcome of a Divine Intervention

Fail upwards

From 14th level, you have mastered the ability to turn failure into chaos. 

When you roll a natural 1 on an attack role, ability check, or saving throw a burst laughter erupts around you:

  • You gain temporary hit points equal to your bard level. These temporary hit points last for 1 hour. And, 
  • Roll 1d20 to determine one additional effect from the manic magic table: 
    d20 Manic Magic Effect
    1 Invisible but Noisy: You turn invisible for 1 minute, but your footsteps make loud squishing or farting noises when you walk. You have advantage on Stealth checks against being seen, and disadvantage on stealth checks against being heard
    2 Confetti Explosion: A burst of colorful confetti explodes from you. All creatures within 10 feet of you are covered in confetti and have disadvantage on Stealth checks for 1 minute. The next attack against each confetti-covered creature is rolled with advantage. 
    3 Bubble Shield: A thick, foamy shield of bubbles forms around you, granting you +2 AC for 1 minute. The bubbles pop harmlessly but make communication difficult, giving you disadvantage on Charisma-based checks.
    4 Jester's Hat: A colorful jester's hat appears on your head, and the heads of all creatures within 30 feet of you, jingling softly. Creature cannot take off the hat, but have advantage on Charisma based checks but disadvantage on Stealth checks for 1 hour. 
    5 Laughing Gas Cloud: A 20-foot-radius cloud of laughing gas centered on you appears. All creatures in the area must make a Constitution saving throw or burst into uncontrollable laughter, falling prone with laugher. 
    6 Poof: For one minute, at the start of your turn roll a charisma saving throw against your own DC. On a failure you vanish in a puff of smoke, reappearing in a random space you can see within 30 feet of you. You can choose to fail the save. 
    7 Mirror Image Prank: Three illusory duplicates of you appear in your space, mimicking your movements and actions except in a more exaggerated and goofy way. The duplicates last for 1 minute or until destroyed. A creature which hits you with an attack must roll a D20, hitting and destroying one of your mimics on a 7 or higher.  
    8 Inflatable Costume: Your clothing magically transforms into a comically oversized inflatable costume, making you look like a giant animal or cartoon character. You have disadvantage on Dexterity checks but advantage on Charisma (Performance) checks for 1 hour.
    9 Rubber Legs: Your legs turn into rubbery, wobbly limbs for 1 minute. Your movement speed is halved, but you can jump twice as high and far.
    10 Pratfall: You fall prone in an exaggerated manner. You gain temporary hit points equal to your Charisma modifier and can immediately stand up as a free action. Allies within 10 feet of you gain temporary hit points equal to half your Bard level.
    11 I'm Flying!:  All creatures in a 30 foot radius must succeed on a Wisdom saving throw or be under the effects of the levitate spell for 1 minute. They may choose to fail this save if they wish. 
    12 B A N A N A S: The area around 30 feet around you becomes slick, as if a single giant banana peel. This area is considered difficult terrain, and creatures must succeed on a Dexterity saving throw while moving into or out of the area, falling prone on a failure.  
    13 Balloon Animal: A harmless balloon animal in the shape of a creature of your choice appears and follows you around for 1 hour. The balloon animal can perform simple tricks on command and distract enemies. 
    14 Duplicate: You take on the form of the closest creature (of a similar shape and size) to you for 1 hour. 
    15 Fart Sound: A loud, comical fart sound erupts from the area around you. All creatures within 30 feet of you must make a Wisdom saving throw or be distracted, giving them disadvantage on their next attack roll or ability check. You and your allies have advantage on this save. 
    16 Pies Everywhere: For 1 minute, at the start of your turn, a pie magically appears and hits a random creature within 30 feet of you in the face. They take 1d4 pie damage (psychic), deducting the same amount from their next attack roll. 
    17 Slide:  You and all creatures within 30 feet of you must make an Intelligence saving throw, on a failure, for 1 minute when you move, your movement speed is increased by half, but you can only move in a single direction, as if the ground was slippery
    18 Rubber Chicken: A rubber chicken appears in your hand. You can use it as a melee or ranged weapon, dealing 1d4 bludgeoning damage and causing the target to make a Wisdom saving throw or burst into laughter, falling prone. The chicken reappears in your hand at the start of your turn for 1 minute. 
    19 Sticky Shoes: For 1 minute your walking speed is reduced by 10 but you have a climbing speed equal to your walking speed, and do not need to use your hands to climb
    20 Up in lights:  Near blinding lights flicker and flash around you for 1 minute, casting bright light for 30 feet around you and dim light for 30 feet further. You swear you can hear faint cheering. You can add 1d6 to any Charisma saves or checks for the duration. 

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