Damn and he's actually totally pulling it off too

Not even slightly.

She is a bad mum for raising a kid who wants to be Mr. Burns though.

I did that once when I was much younger. Went out for a walk and lunch while wearing a hat and not having said anything about it to my girlfriend at the time, then just removed my hat when we were sat down at the restaurant and pretended like nothing was unusual. Did it just for fun and to see what would happen. Turned out we ended up engaged and happily married for many years.