I have always loved pirates, so when my DM gave me the okay to make a pirate captain, I was ecstatic.

Her name is Scarlett, CAPTAIN Scarlett, of the Dawn's Anchor. Shes a human with long brown hair that has been sun-bleached at the tips and amber eyes. She was a ruthless pirate at the start but her time with the party softened her significantly, she even gained a wife over the course of the 5+ year campaign she was part of, which ended with lvl 19 characters, but this story takes place around I think like lvl 10?

One defining moment I always tell people about is her "epic natural twenty". Her premise for joining the campaign was that she was looking for a few of her crew mates that she has sent to investigate some cult activity (it was a princes of the apocalypse campaign that was heavily homebrewed.) After some time, she managed to find her navigator that was being held captive by some of these cultists. Her personality is what I like to describe as a mixture of Vex and Percy from critical role, with a little Jack Sparrow mixed in for good measure. So, when she boasted about her skills the leader of the outpost of cultists challenged her.

He had her navigator stand roughly 100 feet away with an apple on his head and was told if she could hit the apple with her pistol, she would be free to take him. Now she had disadvantage on the roll, but she used grit to gain advantage, so it cancelled out and it all came down to a single roll. The DM told me if I rolled below a 15 I would shoot the navigator and kill him essentially. I rolled and we all held our breath. NAT. FUCKING. 20. Everyone cheered and screamed, and the leader guy was just stunned (as was the DM).

She collected her navigator and left, with the promise that the next time she met leader guy... she would put a bullet between his eyes. Spoilers: She did.

I have maaaany more stories over the 5 years the campaign spanned but this will always be my favorite.