Adventures in good music
I won’t regale you with my Karl Haas impersonation. But give a listen to what’s at the top of my iTunes playlist.†
Jazz-wise, I can’t get enough of Jazz at Oberlin. This is Dave Brubeck’s original quartet at their very best. But don’t just take my word for it; Brubeck himself once said that the early live recording made in my hometown was “the best thing we’ve ever done.”
On the classical side, Emanuel Ax is the man. His rendition of Brahms’s Händel Variations is just unspeakably wonderful, although I’m not too fond of what he does with the rest of the Brahms on this record.
† This is a good time to mention that I’ve become an iTunes user. Windows Media Player and Winamp can no longer compare with it. Version 4.6 still isn’t great at handling classical music libraries (no media player is), but Apple sure knows UI. 
Interesting that you’re using iTunes. Apple has a pretty good history with UI design, though not a perfect one. In fact, their iLife suite (of which iTunes is a part) perpetuates some of their more unfortunate UI decisions: the ‘brushed metal’ theme that originally surfaced in QuickTime player a while back.
One thing Apple has no track record with is building good Windows software (aplogies to those who think the above oxymoronic). DRM requirements notwithstanding, I’m wary of any mp3 player that installs services on my PC.
On a side note, I’ve recently gone back to WinAMP after several years near exclusive use of Musicmatch Jukebox. MMJB was novel in its day, but I really don’t have need of the music store and I find their pay-to-play streaming service becoming less and less useful once I found ways of streaming my own MP3 collection.
I agree with you on the brushed-metal effect. I’m not wild about Apple’s look and feel as rendered on Windows, but they have the important part of UI right: the features you need most, implemented in the most effective way. In particular, I can’t live without iTunes’s Smart Playlists. It amounts to having a query language for finding stuff in your music library. Party Shuffle is also executed well.