D&D 5E How would you make a musician who sold their soul at the crossroads?

Whizbang Dustyboots

Gnometown Hero
As per the legend of Robert Johnson: A musician seeking unearthly musical skill, glory and all that comes with it, sells their soul at the crossroads to an infernal being.

How do you make that character for D&D? Bard? Warlock? Something else?
 

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Tongue in cheek - apparently I'd make sure the DM knew I was a PC so that the loss of the soul and any other deal never comes into the game again unless I put it there.

Seriously - I'd go bard and think of working out with the DM some extra costs or obligations that would kick in that would get me an extra ability or the like (maybe once a day on a long rest?). Like maybe the option of subbing out a bard thing on the fly for a warlock thing.
 

That's not really unearthly ability, though, is it? I admit to not being terribly familiar with warlocks, but I'm not seeing anything like Expertise to boost Performance way up.
Warlock, Entertainer Background
  • Beguiling Presence (Invocation) for proficiency with Persuasion and Deception
  • Prodigy or Skill Expert (Feat) for expertise with Performance
  • Fey-touched (Feat)

or

Bard
+ Haunted One background
or
+ Far Traveler background. The feature is perfect for the classic ''dark stranger'' with musical talent from out of this world who crash a party to reap the souls a soon-to-be bride. ( a common tale in Québécois tales)

with Eldritch Invocation Bewitching Whispers/Beguiling Presence
 



Mike Myler did a Leannán Sídhe with the Inspired Infatuation ability - a cham that caused the target ongoing Wis damage in return for +1d8 bonus to ability checks and saves.

You could use a similar mechanic for a Bard with a infernal contract on their soul


Inspired Infatuation.

The leannán sídhe uses its bonus action and action to target a humanoid it can see within 30 feet that can both see it and hear it. The target makes a DC 18 Charisma saving throw or falls madly in love with the leannán sídhe and becomes charmed. Whenever the charmed target makes an ability check, attack roll, or saving throw that is not against the leannán sídhe, it gains a +1d8 bonus. While the target is charmed by the leannán sídhe, once per day the fey can give it any command short of an activity that would result in certain death. When the leannán sídhe does so, the charmed target may make a DC 18 Charisma saving throw to resist. At the end of every long rest the charmed target makes a Charisma saving throw against the leannán sídhe (DC 10 + 1 per previous successful save) or its Wisdom score is permanently reduced by 1. The charmed target dies if this reduces its Wisdom score to 0. A target remains charmed until it makes 5 successful consecutive saving throws, the leannán sídhe dies, or the fey chooses a new humanoid to charm with Inspired Infatuation.
 

I'd write a bard subclass especially for it, to be honest. It's kinda begging for one. Expertise in either Performance or one musical instrument, and when using that proficiency in competition with another, you get advantage on rolls (the ability is of course called 'best there's ever been').

A few fiendish-themed spells at higher level. Hellish Rebuke, fiend summonings etc. The 'sold your soul' bit I think can be handled through roleplaying just like a warlock's relationship with their patron is, or a cleric's with their deity. After all, there's also the bards who challenge the devil to a fiddling competition, stake their soul, and win, and get away scot free - for now.
 

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