I've been following the maxim "less is more" in some areas of my life lately. Hence, the iPod went off to e-Bay. But I still gotta have my music - so here's what I do:

Bose Quiet Comfort 2 headphones

J. River Media Center 11 (the Alpha version)

and, on longer flights (with no Power Port adapters), I borrow my co-worker's:

Valence N-Charge battery - adds 10 hours or so to your computer's run time.

I just copy 20 GB over the night before my departure and I've got tons of music for my trip. My laptop plays well - even when the top is closed and in the seat pocket ahead of me. Once less device to carry. And that is a Good Thing. ^