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You should try looking at http://www.synapseai.com/. They have a great player that does exactly what you've suggested. They also have a winamp plugin called "The brain" which works pretty well too, except that it plays all file types(including video) from your library. It doesn't really suggest anything that you have never played yet though. It simply listens to your habits, and suggests songs(or video) that you already played.

An interesting note on BuddyZoo and degrees of separation -- it was created by one of the creators of Synapse, the other co-creator being the creator of thefacebook.com, with whom I worked on a small project several years ago.

One of my favorite WinAMP Plugins is The Brain, which monitors your listening habits and begins automatically creating its own playlist for you. Just choose music for a week or so and then let The Brain take over... Kind of like having your own radio station. The plugin hasn't been updated in a while, though. Are there any other audio players with built-in or plugin capability to do the same?

Random/shuffle is soo yesterday!
Transparent adaptive playlists frameworks (eg: Synapse (Windows) or IMMS (Unix)) are totally the way of the future! I am surprised more hardware mp3 player manufacturers do not ship their players with software like that.

Intelligent shuffling with synapse

Smart playlists? Try The Brain also available as a Winamp Plugin

If you want the ultimate in genre music, try Moodlogic:

MoodLogic Mixes change the way you think about your MP3 collection, whether it is on your computer or on your MP3 Player device. Over the last three years, tens of thousands have contributed to MoodLogic more than a billion survey answers on how they feel about music. MoodLogic has assembled these answers and created the world's largest music database. After years of research and development creating complex computer algorithms to clean up the user-contributed data MoodLogic built an industrial-strength infrastructure to serve it back to you. Now you can experience your music in ways you never thought was possible*. Automatic music organization, intuitive MP3 mix generation, and robust ID3 tag cleanup are just a few of the highlights of MoodLogic.

Moodlogic is superb - it drives my home music collection. I ask my server to play slow electronica between the years 84 and 92 and it just does it.

Live searches? In WinAmp just press the "J" key and start typing.

Smart playlists? Try The Brain also available as a Winamp Plugin

If you want the ultimate in genre music, try Moodlogic:

MoodLogic Mixes change the way you think about your MP3 collection, whether it is on your computer or on your MP3 Player device. Over the last three years, tens of thousands have contributed to MoodLogic more than a billion survey answers on how they feel about music. MoodLogic has assembled these answers and created the world's largest music database. After years of research and development creating complex computer algorithms to clean up the user-contributed data MoodLogic built an industrial-strength infrastructure to serve it back to you. Now you can experience your music in ways you never thought was possible*. Automatic music organization, intuitive MP3 mix generation, and robust ID3 tag cleanup are just a few of the highlights of MoodLogic.

Moodlogic is superb - it drives my home music collection. I ask my server to play slow electronica between the years 84 and 92 and it just does it.

Live searches? In WinAmp just press the "J" key and start typing.

I've updated the FAQ, so some of the questions people are asking should now be answered. There are also some work-arounds for a couple of the bugs people have reported. Thanks for all the feedback guys -- keep it coming!

I want to offer the following information about the project. The majority of development effort went into building the Brain. The Synapse player is just something we threw together to get the most from the Brain's functionality. We will probably never port Synapse to other systems since more than enough players already exist. Synapse does work under Wine though. We do have plans to bring the Brain to other systems, and we've begun by writing a plugin for Winamp 2.x, which you can get here. An XMMS plugin is coming soon, and then hopefully there will be one for iTunes in the near future.

And a note about privacy. None of your musical listening data will be available to anyone other than you. We hope to use massive amounts of data to aid in analysis, but your individual data will never be seen by anyone else.

I want to offer the following information about the project. The majority of development effort went into building the Brain. The Synapse player is just something we threw together to get the most from the Brain's functionality. We will probably never port Synapse to other systems since more than enough players already exist. Synapse does work under Wine though. We do have plans to bring the Brain to other systems, and we've begun by writing a plugin for Winamp 2.x, which you can get here. An XMMS plugin is coming soon, and then hopefully there will be one for iTunes in the near future.

And a note about privacy. None of your musical listening data will be available to anyone other than you. We hope to use massive amounts of data to aid in analysis, but your individual data will never be seen by anyone else.

Music to my ears. Hm. Ok, here goes:

20G+ iPod (Apple hasn't a prayer of holding my entire music collection, but let's at least get a decent sized chunk of it, shall we?)
Bluetooth (or WiFi, whatever) connectivity.
Induction charger.
Some way to intelligently decide what should go on the iPod. The Synapse thing would be good here, methinks.

I'd like to come home, toss my wallet and keys and toys on a mat by the door, and have everything there automatically charge, sync, and get ready for the morning. Without any intervention on my part.

If Apple made an iPod / PDA comparable to the tiny Sony Clies with the gorgeous displays and included a wireless charger/sync combo, they'd have my business in a second. I would pay a $50 premium for that without blinking, and maybe $100. Convenience rather than power is Apple's game, and I'm eager to see them capitalize on their strengths in non-PC sectors.

This is a lameass Visual Basic app.
Not that there's anything wrong with that...
I'm not holding my breath for the XMMS version though.