McGonagall - Foster Jenkins - Wiseau

[RyanW]

Then you also get people like Jack Benny. I've heard those that know the violin can tell the difference in a bad violinist (which is just unpleasant to listen to) and a good violinist hamming it up (like Mister Benny). He probably wasn't good enough to make it rich just playing the violin -- though he did get his start as a violinist in vaudeville -- but turning it into a comedy prop was what started his path to stardom.

[Stone Dog]

I heard Wisseu is independently wealthy and paid for The Room out of his own pocket. There was no convincing of others to fund his vanity project.

[A Ladder]

To make someone really bad at something I would give them the Incompetence (skill) quirk and Delusion (I have said skill and cannot fail at it). This means they try something at default but at a further skill penalty....giving you a person who is terrible at what they do.