What spurred my desire to have a portable music device (in my case, my cell phone) was my reintroduction to public transit. I hadn't used buses and trains to the extent I do now since I was living in the Washington, D.C. area from 1998-2002. Back then I carried a Discman which would skip if I bounced it around too much.
Since moving to residential Minneapolis and abandoning my vehicle, I've been making use of my noise-cancelling earbuds. As an introverted woman riding on a bus, I find them invaluable. I can pretend not to hear someone if they're talking to me (helped even further by keeping my nose stuck firmly into a Stephen King novel) and can ignore the everything around me without seeming as rude as I might without the earbuds.
What surprised me is how often I use the earbuds while simply walking around at school. I often haul them out when I find myself unwillingly subject to a conversation that makes my eyelid twitch. (At the risk of sounding too get-off-my-lawn, I popped them in before class once when two separate conversations around me produced approximately 50 "like"s in the space of about two minutes.) They're also very handy when someone on the bus decides to hold a curse-laden conversation at full volume with someone on the other end of their cell phone, which happened just today.
I do sometimes enjoy the soundtrack-of-my-life aspect of having music playing as I move about, but for me it's mostly a tool of isolation and distancing. There are times when I wonder if I'm missing out... like yesterday, when a cute girl getting off at my stop seemed to be saying hello, but I missed it because I had my earbuds securely planted. But for every possible missed opportunity there are a hundred times when I would hate to be without them, so I imagine it won't change anytime soon.