iTunes Agent:

"iTunes Agent is a tiny application which rests in your system tray, constantly looking for devices being connected to your system. If a device it recognizes is connected it enables you to manage it via a playlist in iTunes. You may even associate your player with a Smart Playlist, such as 'Party Shuffle', and always have a new collection of tracks on your player!
When you are done modifying the list of tracks for your player you can synchronize it with two small mouse-clicks!iTunes Agent is a tiny application which rests in your system tray, constantly looking for devices being connected to your system. If a device it recognizes is connected it enables you to manage it via a playlist in iTunes. You may even associate your player with a Smart Playlist, such as 'Party Shuffle', and always have a new collection of tracks on your player!
When you are done modifying the list of tracks for your player you can synchronize it with two small mouse-clicks!"