The Stain'd Playhouse was a theater located in Stain'd-by-the-Sea.
The playhouse had held numerous performances of a variety of plays. Some known shows that were performed there are:
- The Letter - Dame Sally Murphy as Leslie Crosbie.
- Shiver Me Timbers - with a large pirate ship set that had working rigging.
- Mother of Icarus - also starred Dame Sally Murphy.
- Look Out for That Train Wreck - with a large train set that could be split apart.
- The Man Who Looked Somewhat Like Winston Churchill - featuring Mr. Mann.
The theater remained open for over fifty years, but when the economic collapse hit Stain'd-by-the-Sea, it was forced to close. Whether it was abandoned entirely or reopened later after the conclusion of the All the Wrong Questions series sadly remains unknown, though the former is more likely. 
- Billy Becker - Stagehand
- Hans Mann - Set Builder
- Hans Mann's Sister - Costumer
- Mr. Mann - Actor
- Old Lady Mann - Ticketseller
- Dame Sally Murphy - Actress