College of Sorrow

Bards tend to be thought of as merry, boisterous Minstrels. However, some who have the talent and inclination to play, are of a different mind. Instead of folk songs, sea shanties, or even elegant songs of the court, they play songs of sadness; touching, moving, and emotional; beautiful in their own way. But beware, for should you draw their ire, you will feel that same sorrow tenfold; For bards of this small outcast college, the phrase "dying of a broken heart" has a much more literal meaning.

Melancholy Melody

At level 3, your Bardic Inspiration, which used to be a cheerful, motivating tune, that encouraged allies helping them complete the task at hand, has now become a demoralizing dirge that inflicts foes with a debilitating sorrow. The effect of Bardic Inspiration and the type of the according die is replaced by the following: As a reaction to an enemy that you can see and that can hear you making an attack roll, ability check, or saving throw, you may expend a use of Bardic Inspiration to reduce the roll  by 1d6+1. You may know whether or not the roll succeeds or fails before you use this ability, but not what the result of the roll was. This decrease becomes 1d8+1 at level 5, 1d10+2 at level 10, and 1d12+2 at level 15.

Inspiring Anguish

At level 3, you can now draw inspiration from great sorrow in order set misery upon your songs anew. When you use a bardic inspiration to decrease a target's roll, if their roll is decreased to 5 or more below the DC for the roll, you regain a use of bardic inspiration. The DM may also choose to grant you additional uses of bardic inspiration and/or otherwise impower you in moments of extreme sorrow (Don't harrass them about this, it's just an extra little fun thing. Just let them know about it, and if it happens it happens. Let it add to the impact of a story moment).

Voice of Misery

At level 6, your voice now carries a pervasive sense of somberness, making your those who hear all the more receptive to the sorrow you would wield against them. You have advantage on all performance checks that both involve your voice and are meant to invoke a sense of sadness. Additionally, spells and cantrips you cast that invoke a magic voice against the target, such as Vicious Mockery, Dissonant Whispers, Suggestion, and Enthrall (NOT spells like hideous laughter. It is you making the target laugh, not you creating and using magical laughter against them. Vicious Mockery, Suggestion, and Enthrall count because they lace your voice with magic), give the target disadvantage on the saving throw to resist the spell. The DM gets the final say on whether an ability check or spell count for this feature.

Lingering Grief

At level 6, the sorrow you inflict now entrenches itself more deeply into a target's psyche, persisting and continuing to affect the target for a time after. Whenever a target is subjected to the debuffing effects of Melancholy Melody or Voice of Misery, all further attack rolls, ability checks, and saving throws they make before the start of their next turn are reduced by 1. This reduction can stack. 

Agonizing Sorrow

At level 14, the weaponized sorrow you inflict grows sharper, causing pain to those who have the misfortune of being subjected to it. When a target fails a roll that has had the effects of Melancholy Mindset, Voice of Misery, or Lingering Grief applied to it, The target receives psychic damage equal to the amount by which the roll failed (you may choose for this effect not to occur). If both Lingering Grief and either of the other two are applied, the damage inflicted by this feature is increased by the total value of all negative modifiers, no matter the source, applied to the roll (If the roll had disadvantage, the difference between the higher number and the lower number is counted as a negative modifier for purposes of this feature).