I got interested in the #musicadvent thing a little late. If you don't already know, you're supposed to start with 1989 and pick a song a day, one for every year up to the present. This is where being middle-aged catches up with you a bit, though - by 1989 I was married and working and not paying that much attention to music, although I always kept up to some extent.
Since I don't want to go back and post my (not exactly ground-breaking) picks on twitter, I'll do it here. For 1989, I'll go with the #1 song that year, because I liked it then and I still love it now, and that was Madonna's "Like a Prayer" - see, not exactly ground-breaking. I was never a gigantic Madonna fan, and in fact I was one of many people that mocked her roundly early on. But along about "Like a Virgin" I kind of went, okay, maybe she's not just another dance-music girl. I just looked on iTunes and I have some 7 Madonna songs, mostly the big hits. I thought I had bought The Immaculate Collection at some point but maybe not. (Or maybe yes, and it was on CD and never got onto the computer. Who knows at this point.)
Looking at 1990, no particular songs stand out, but I notice that it's the year Stevie Ray Vaughn died. I was living in Austin in the first half of the 80s when he was still there. Unfortunately, I only saw him perform once, and I was so wasted I barely even remember it. I was about three feet away from him at one point, though, so that is my brush (sort of) with fame there. Anyway, it made me very sad when he died. Helicopters are dangerous, kids.
1991... hmm, I was thinking this might be where I talk about Pearl Jam, but maybe it's where I talk about R.E.M. instead. 1991 seems to be when "Losing My Religion" was released, which I think was their first big commercial hit - at least that's how I remember it - and it's another song that I still really love, even though it's been massively overplayed. Once again, I was in Austin in the early 80s and so I picked up on R.E.M. pretty early, although I remember that when "Murmur" was the big thing that I didn't really see what all the fuss was about, although I did like "Radio Free Europe" from the beginning. I think by the 2nd album they had pretty much reeled me in, though. (Wikipedia says that Murmur only sold 200,000 copies but it was getting all kinds of hype, and living in a place like Austin, you picked up on things kind of ahead of the curve!) I did see them live once, I think along about 1984 or so, and they were great.
I say I kept up with music in this period, but actually I know very little about the pop music of the 90s. Looking at the top 100, I don't remember at least half of these songs at all.
I'm looking at 1992 and nothing has grabbed me yet, so, maybe I'll stop where I am
. Late addition for 1992, after looking at other people's picks:
("Would?" Again, not exactly an avant-garde pick, but a song that seemed pretty groundbreaking at the time, AND has held up really well.)holidailies.org
Since I'm still editing, here's "Losing My Religion", too: