I guess it depends on what you mean by a song. If we are counting all songs regardless of purpose, I think the Operatic Orange skit is the first thing I remember hearing (though I probably heard the Sesame Street theme song beforehand):
As for popular music, I probably heard Cyndi Lauper's "The Goonies R Good Enough" before anything else:
I'm not sure which came out first, Pac-Man Fever or Shock the Monkey. I was young enough for both that I thought I could just say the name of the song and it would play. But it could also be the jingle for a Colt 45 commercial, though I can't find the exact one to get a date on it... who knew there were about 80 zillion Colt 45 commercials?
I actually just recently had this 'awaken', at least excluding music in kids' movies and shows. The earliest song I can remember actively was a song a co-worker reminded me of. The song's name is my first name, and when I was really little I got a kick out of the act my name was a song and I thought it was about me (I did not pay attention to lyrics) so she'd play it for me a lot. Now it's probably one of the strongest memories of her I have.
You said the oldest one, I was going to send one from 40 years ago but the first one I thought of was this one... I feel a little embarrassed but here it is:
It would probably be something like my grandmother playing Frank Sinatra. But if you mean something contemporary from when I was young, this was all over the radio and one of the earliest songs I remember hearing when it was new. Wake Me Up Before You Go-Go by Wham!
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