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

[Unwise]

I'd just play a bard. Not everybody is born with PC level stats.

My PC was born with Charisma 6, he was always the butt of jokes and bullied. He could never hope to woo the woman of his dreams. He was physically frail too. As he approached adulthood, he made a crossroads pact to be just like the super popular, handsome, athletic, magical guy who was the object of his envy. The PCs wish was granted, in exchange for his soul. The object of his envy withered away as all that was good was stripped from him, horrifying the PC and showing just how evil the pact really was.

It sets up for a dip into Infernal Pact Warlock and is one of the few character concepts that makes that popular dip make sense storywise.

 

[Kurotowa]

But that's the thing! Why would they trade away their soul? They are good (high cha) but not amazing...

Here's a trick of character creation I've sometimes used. Your starting ability scores don't have to reflect your character as a blank slate Level 0. They can include influences from other character features as justifications for why they're high (or low). For example, one of the two Ravenloft PC ideas I have set aside is for a high Strength dhampir who was a sickly weakling before they were infused with the elixir that gave them strength, health, and unnatural thirsts.

So maybe the imaginary Level 0 version of our musician was a Cha 8 nobody and part of the pact that came with Warlock powers also boosted them up to a starting PC level Cha score. It's nothing with any mechanical backing, just a background point that they used to be ugly or lack self confidence or just didn't know how to read a crowd, but now they've been transformed into a better musician than they ever dreamed they could be.

 

[Ancalagon]

Here's a trick of character creation I've sometimes used. Your starting ability scores don't have to reflect your character as a blank slate Level 0. They can include influences from other character features as justifications for why they're high (or low). For example, one of the two Ravenloft PC ideas I have set aside is for a high Strength dhampir who was a sickly weakling before they were infused with the elixir that gave them strength, health, and unnatural thirsts.

So maybe the imaginary Level 0 version of our musician was a Cha 8 nobody and part of the pact that came with Warlock powers also boosted them up to a starting PC level Cha score. It's nothing with any mechanical backing, just a background point that they used to be ugly or lack self confidence or just didn't know how to read a crowd, but now they've been transformed into a better musician than they ever dreamed they could be.

While I like the elixir granting strength concept, when I said "they don't have what it takes" I didn't mean "their cha is too low". Maybe they are tone deaf and their singing voice is poor. Maybe they don't have rhythm. Maybe they aren't attuned to the universe's harmonies and thus can't manifest bardic magic, can't achieve those great level of skills. There is a reason why this character can't make it as a bard, why they made a bargain with the devil...

.... well turns out the devil can't grant bardic music either. But he can grant you power, and infernal luck....

 

[Faolyn]

I realize I'm late to the thread, but my friend always wanted to play a celestial-pact warlock who did this so he can say he sold his soul to the deva down at the crossroads.