So, two members of my party are being held in jail, and they were both of our damage dealers, so we couldn’t mount an assault to get them out. On Tuesday at 5 pm, a royal official was to come and pronounce a sentence upon them, and with the crimes they had committed (Theft, arson, kidnapping, assault, murder, and jaywalking), the sentence wouldn’t be good
A normal D&D player either gives up on this situation and leave them to rot, or runs a stealth mission to break them out undetected. A bard looks upon fortune, and smiles.
My bard character dyed his clothes to look more royal, made his caravan look like a prison transport, and forged documents with the royal seal. I then marched right up to the front gates of the prison, and pretended to be the royal official. When asked for identification, I waved forged papers in front of their face too fast for them to get a good look at, and demanded to see the warden.
When I met the warden, I told him that their crimes together comprised a case of BurgleArsonLarceny, which the king had declared an offence to be tried by him personally (all of this was complete and total bullshit, even in D&D). I told him I was to expedite the prisoners to the capital for their trial, and I would need all their equipment as evidence. He believed me, and he loaded up the prisoners onto the cart. As soon as we were over the horizon, I let them out, and we rode out into the sunset.
This is further proof of why Bard is the best class.
tl;dr: I broke my friends out of jail by pretending to be a court official, and telling the warden that burglearsonlarceny was out of his jurisdiction.