The only funny boob jokes in anime I can think of are in series that were otherwise pretty garbage.

The cell phone in Citrus and the shirt in Asobi Asobase.

that seems less 'BIG BOOB SEXY' and more just relatable boob problem

precisely

I feel like it's because only series that are actively angling for the Garbage Fan audience are willing to do any boob jokes for sensible reasons

So they'll hit a good one eventually just on statistics

Was it Rurouni Kenshin where boobs turned out to be bombs?

No that was Samurai Champloo

Also man I’m mad Asobi Asobase went bad because it was hysterical until the transphobia happened

I liked the one in love live where they're chasing nico through the street and nozomi's too busty to fit through a gap in between some parked cars that nico went through

so they send rin through the gap instead while she huffs the whole time

that got an actual irl laugh out of me

I forgot about that.