The sort of men who come out with phrases like that are (almost universally) arseholes. Having a default response, that can be rolled out quickly, and hit at emotional sore spots is useful.
As for why it works, if they are willing to come out with that line, then either a massively misogynistic, or badly socially stunted and rude. Both will drive women away aggressively (and likely a lot of male friends).
Still, you can expect a comeback to not be a complete offtop.
Yes, the first phrase has a goal of embarrassing the owner of the t-shirt, but comeback in the style of "yo momma is so fat that..." is embarrassing to the giver, not to the receiver.
Even "Can YOU name 5 songs?" would be much-much better.
"Can YOU name 5 songs?" would be much-much better.
Holy shit, no it is not. This is like dousing a grease fire with water.
If someone is coming at you with a "prove you're a real fan" question, they've got friends or they've got a video camera. The last thing you want to do is appear desperate.