Purely because he is a big music fan with lots of music knowledge and, even if he didn’t know the name of the band, I assumed he would have at least recognised the songs when I played them to him.
But when? Like let’s say the most likely way you hear old also ran bands these days is in a rabbit hole of “also listened to” on spotify. Or on a tv or film playlist.
He’d have to have an interest in some sort of link, and like that enough to listen to some more “similar”. So who is going to lead you to squeeze? I can’t think of it popping up on a tv show or film. So similar music?… Joe Jackson seems unlikely. Elvis Costello? More likely. 10cc? Possibly but none of them are exactly pumping them out these days so unless you already have an awaredness i don’t think its that surprising.
Some bands just don’t stand the test of time and just fade away. And as someone alluded to… Its a bit… Tedious. Cool for cat is great as is take me i’m Yours too. But alot of it is croony guff.