Can not delete mp3's

So I've got about 5.3gigs of music on my 8gig phone. For what ever reason when I delete songs from the phone in iTunes it doesn't free space. I've deleted over 3 gigs of music from my phone and yet it still sits there with 35megs free. Whats the deal? How can I recover my free space?
EDIT: It looks like when I delete a playlist it doesn't remove the music from the device, so now it's all unsorted in the Music. How can I see only songs that are not in a playlist so I can delete them without having to sift through them all by hand?
Message was edited by: zushiba

Have you ever logged in on a different machine or had a different iTunes account. You may not be able to delete things that are not allocated to your account so to speak.

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