Defeated by Outdated Tech

Gabe loves music.  He is SO big now that sometimes he just likes to hang out in his room and listen to the radio.  He might draw or build with Legos while he's in there, but the other day I walked in and he was just sitting at his desk, bobbing his head along to the music.

How did we get here? 

Recently he mentioned that he wished he had a way to listen to just a playlist of his favorite songs.  (I am embarrassed to say that several of them I had never heard until my child introduced them to me.  Crap, I'm old.)

I dug through the junk drawer and came out with these.

Seriously, guys, when did these things come out?  And why don't I remember how to use them?  Do I even have appropriate chargers for them?  How do I erase the music that is already on them?  How do I add a playlist?  It's like iTunes on my PC is such a distant memory from a year long ago that I can't even recall it.

And to think that when I finally figure out how to make one of these work for my boy, he's going to think it's the most amazing piece of technology that has ever existed.

Just wait, kid.