I've tried on longer rides, like through France, but the headphones are a pain in the arse (I think I might have put them in wrong...) and you lose a lot of the sound to external noise anyway.
You might be better off with some inner-helmet speakers, but it will still be fiddly to change the track, change the volume (too loud when stopped, not loud enough when moving) and it will be a distraction.
Anyway, what's wrong with singing your own tunes like the rest of us?
