Crenthle's Calamitous Conundrums

A quiz show, run by a lich or similar (unseelie fey, a demon with a sense of humor...). Make a series of questions about in-game knowledge your PCs could have, then set up multiple choice questions and bonus rounds with fun games. Get a question right, earn a magical prize! Get one wrong, and Crethle eats a bit of your soul (max hp reduction). At the end of the game, you can walk or you can fight the host for your hp back (restored after a long rest IF the lich has been destroyed recently/is occupying his phylactery).

Run the lich as a malicious Alec Trebek. (or Regis from Who Wants to Be a Millionaire, or Trapp from Um, Actually)

Questions might be, like:

Laeral Silverhand has six sisters. What a family! Name as many as you can. (3 is a success, more is bonus loot)

The catoblepas is among the many reasons I won't be visiting the Dead Maers. Draw one for me!

The capital city of Cormanthyr, until its recent destruction, was the seat of power for a thousand years. What was it called? A) Mistrannor, B) Myth Drannor, C) Clevelandohio, or D) Silverlake.

After, say, five questions have a combat. After ten a bonus round where they can grab as much loot as possible in a series of skill checks. After fifteen a trap or danger room. Repeat for 25 questions (so a group of 5 gets 5 each) or until bored. Then: fight a lich, or leave the castle!