I'm going out for a 16m run around NYC (Brooklyn to Queens to Manhattan and back home to Brooklyn) I'll take mine with me (2GB shuffle, which is light with like lots of music on it). I shuffle through different music or stay on one band if i like the pace or mental space it helps me maintain. I have lots punk, dub, pop and most of it inspires me or fixes me into an emotional state. being a musician I'm very prone to be struck by the power of music but while I'm running I dont always focus on the instrument I play, I find a lot of other nooks and crannies in the music.
all that being said during times that I dont know the path i'm running as well, in busier areas or low visibility I will either turn off/pause the ipod or lower the volume to almost nothing for the sake of safety. Additionally, its always a good idea just to turn it off for a while and "unplug" from the world around me.
one other thing, I've heard from other runner friends that motorola is coming out with a watch/gps/heartrate monitor/mp3 player that not only can you download music to while mobile but that analyzes your heart rate with regard to the music being played and will play music accordingly if you set your watch for a target heart rate workout and if you need a "power/speed/pace boost" you can press a button to immediately play songs which tend to increase your heart rate and therefore pace/speed. crazy right? supposedly its like $1000 but its been seen on people wrists.
Wow. that was a long answer. happy running and have a great holiday season and happy new year.