I know this isn't really a boombox topic but I think boomboxes and headphones go together. For me sometimes hearing every component of the music means putting on a good set of headphones and plugging them in to a powerful receiver and letting it rip. Even on lower settings it truly is the best listining environment for audiophile quality listening. When at home my favorite headphones are my Sennheiser HD800's...they have deep solid bass reproduction and the sound quality is simply amazing...but they don't come cheap ($1400). When using the mp3 I have 2 sets of headphones: Sennheiser PX-100's for over the ear listening and Sennheiser CX-500 for in ear isolation. Both are excellent portable phones with excellent clarity and surprisingly deep bass and crisp highs and they are both very reasonably priced ($50-$120) on most websites. You will not find a better headphone in that price range.