Rolled a Nat 20 on bluffing to be an actor, need to write a play.

Thanks for the responses so far, read them all even if I haven't replied to them all. So far I've decided that the play should be in three parts.

ACT 1: Romantic comedy, staring my character as himself, seducing a noble woman's more attractive, smarter, kinkier sister. (Dropping enough hints that he actually got the worse sister, but hey, still a noble woman.) Ends in him being chased out of his homeland by dogs, guards, and the noblewoman's father. Accidentally fathers a bastard.

ROLES: Kaiter (Warlock, main character, highest charisma) as himself

Bastion (Paladin, human female, second highest charisma) as more attractive sister. (Bonus, player is the oldest balding man in the party, completely miscast. His character also hates mine.)

Abriana (Ranger, elf female, only other girl regular character) as less attractive sister. (Bonus, player is the balding man's wife. Far more attractive, her character disproves of mine)

Morthos (Tiefling rogue, male) Noble Woman's father. (Played by another girl, character finds mine hilarious. Easily the most murderous of the party)

Others: Various minor characters, guardsmen, having them RP stage hands (Lighting and prop changes)

ACT 2: Kaiter Gains his Patron, going to have an epic fight and riddles, all done through burning spell slots and major image/minor image/ throwing voices/ prestidigitation. Special effects out the wazoo.

Kaiter, having being chased out of his homeland, has been living in the woods for several months, eating varying kinds of mushrooms and roots and getting hopelessly lost. He befriends a vagrant in the woods. This vagrant spins a wild tale of faeries and magic, and, high on mushrooms, the two actually stumble into a fey circle. Two archfey of the seelie and unseelie court are gambling. They look at each other, decide to use stupid humans as play things. The Vagrant gets turned into a toad after losing (And promptly eaten). Kaiter cheats to win, pissing off one of them, which other one finds hilarious, saving his life and granting him magical powers. The pissed off one gives him his familiar. (A quasit. The quasit is the most horrible NPC in this game, ruins everything for every one. Every character hates it because it goes out of its way to ruin whatever plan they come up with, the players love it because it's goddamn funny.)

No idea who to cast for this one.

ACT 3: Probably blatant fan service to the lord of the castle, or something. I don't know how to end it.

/r/DnD Thread