Sounds annoying. How old is he?
I could tolerate this from an 80+ year old.. I've got elderly relatives who say the same joke again and again, and honestly, at their age, I just laugh along and we get on fine.
But from a younger person, who has had the situation explained to them? That would annoy me. Probably not to the point of exploding, but certainly to saying something firmer.
I do think though generally speaking, that a lot of men, make these comments until they get pushback. The issue is that they are not expecting angry pushback, they are expecting "banter" pushback, because that is how male communication/relationships work. They push, the other man responds and pushes back, but never aggressively, because aggression = chance of violence/fighting in men.
The problem is that women don't communicate in the same way generally, so their "unfunny remarks" will keep not getting the pushback they are expecting (A cutting/insulting/crude joke back) so they just keep on going, ignoring any other response, until eventually the respondent gets angry or complains. At that point they are confused and don't understand what has happened.
Men who actually understand how to communicate, especially with different people, (especially with women) don't have this problem.