I rather like WinAmp 5's "Media Library". I currently have no problem going through my 6906 MP3s at a whim, with easy searches based upon artist, album, and track name at the same time.
I tried iTunes, and I wasn't impressed. It seems to like eating up lots of screen real estate, and just felt counter-intuitive.
If you can bring yourself to using it, some like using Windows Media Player.
If you got really creative, you could use a Linux computer running mpd (Music Player Daemon,
formatting link
which uses what Windows people might call a "network service" to playback MP3s, so you could easily control MP3 playback anywhere in the house from a web browser. Further implementation of coolness with mpd is left as an excersise to the reader.
I however record all my MP3s to vinyl LP, and use those wherever I go, especially when out for a jog or in the car. Because Analog Is Better(TM).
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