I don't have a portable music device, but my Winamp has a lot on its list. I have things that have a ridiculous amounts of listens--stuff that I could listen to all the time. Then there are things I like a lot that follow, and things I like for the rare occasion. I really cannot bring myself to thin out my collection. I have tried and regretted this.
One of my most favorites would be VNV Nation--most of their songs mean a great deal to me or are great fun to listen to. Though I listen to it less now than other various EBM, synthpop, futurepop. I also like Ayumi Hamasaki (remixes mostly), various video game soundtracks from the early 2000s and prior, anime soundtracks (I highly recommend Yoko Kanno--her music varies quite a lot. She's a genius?), Aural Vampire, The Smashing Pumpkins. And many more?