Pavement, "Stereo"
I dunno, I just love Pavement. Just hearing the intro to this song puts a grin on my face. I haven't gotten sick of it yet, and I hope I never do. Pavement will probably be one of those bands that my kids will look back on fondly as reminding them of their old man, and maybe they'll even listen to them occasionally as a result. I'll still be distorting their taste from beyond the grave!
Green Day, "American Idiot"
Another band my kids might listen to in order to ring up memories of my crappy taste, although if they're paying attention, it'll be older Green Day.
Mudhoney, "Thirteenth Floor Opening"
Mudhoney made no particular concessions to the popular market despite arriving on a major label for Piece of Cake. They continued to cheerfully evolve their fuzzy psych garage rock in the directions they chose, without really paying attention to what was getting lots of radio play (mostly dour grunting). This song, for instance, is a classic dirge in the mould of "Come to Mind", and is the sort of tune that mostly wasn't in the repertoire of other grunge bands.
I'd say that today sounds like my dorm room, but alas, that's just not accurate. These three bands, yes, but not these three albums.
Succumb, "Lilim"
You ever accidentally have a couple tabs open playing music, and it's really disorienting for a while until you figure out what's going on? Succumb answers the question of what happens if you make an entire album out of that feeling.
Eric Clapton, "Tears in Heaven"
That's maybe the funniest song that could follow Succumb.