Bjorn the Teacher

DougDoug challenges himself to beat Peggle, but having an AI quiz him. If he gets it wrong, he has to redo the level. After having Chat suggest very specific questions relating to topics outside his wheelhouse, he begs for a broad question about topics that he knows about. Cue someone asking exactly what he requested, all while pissing off the teacher. This leads to a trick question that Doug gets wrong (which also pisses off Bjorn) and when Doug asks what the actual answer is, he's amazed to find that it was a trick question.

Example of:
Artificial Brilliance