The Ballad of Who Could Care Less by the Ben Folds Five is an interesting song that seems to be about a group of friends who are largely disaffected "too cool to give a shit" edgey types trying to out cool each other and it's sung from the point of view of their 'junior member' as it were who's hugely enthusiastic about them and is really stoked to be a friend of theirs, but somehow doesn't get the "too cool to care" vibe, and just wants to make them laugh through various means
this culminates in one of the final lines of the song;
"oh well, maybe not, I'll try again.
This should cheer you up for sure.
See, I found your old ID,
and you're all dressed up like The Cure"
the song pauses for a beat moment there, as if everyone is too stunned to react, then the final chorus continues into its finale, and it feels as if that's when everyone just bursts the fuck out laughing, and the fascade is broken utterly, and everyone's having a great time without faking disinterest.