A friend of mine has begun doing this to manage his MP3s. It's painstaking to set up, depending on your storage system (all of mine are stored by artist and album, so it's taking me a while to set up), but the result is well worth the work. The general idea is to create a menu in your taskbar with shortcuts to your playlist files. That way, for example, if you decide that you're jonesing to listen to an album on your computer, you just pop open the toolbar, and select it from the menu.
First, create a folder for your playlist shortcuts. Next, create playlists for the files you want to put in your MP3 bar menu. Create shortcuts for each playlist, and stick those in the folder. Right click on your taskbar, scroll to "Toolbars", and click "New Toolbar". Direct the toolbar to the folder you made, and it will automatically populate, alphabetically, with all of your playlists. All you have to do then is pop open that toolbar, select the playlist you feel like listening to, and it will automatically open in your media player of choice.
It sounds complicated, but it's very easy. As I said, the amount of time it takes to build your list depends on the number of files you're adding, and the way you've organized them. I reccommend using eags on! to make the playlist files. It shaves a pretty significant amount of time off of the process. It's also a handy application for mass-renaming, and editing multiple tags at once.
Then again, maybe this is just me being really geeky, and having too much time on my hands.
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