Transferring files from Windows, names of songs not correct in iTunes

Question

so I have my music on an external hard drive from my windows machines. The songs 'file names' (what you see on the HD) are correct. When I tried to bring some over to iTunes, via add to library, the info was added as 'Track 1" ect, with no artist or album info. In the itunes music folder, it was sorted as the artist folder (I copied and pasted from my HD)...
I also tried to 'import' from itunes, and still the info was not correct.. when I tried the advance button to get cd info, itunes told me I couldn't do it because i didn't import with itunes, even though I did import from the external HD with itunes....what is going on? Does the 'get track listings' onlyl work if you are importing CDs?
Also since itunes just looked at the files as 'track 1' etc, that means the MP3 file did not have the correct tags, so I have re-enter everything? That the files I was seeing was just the names I gave the MP3? Does this mean I have to go back and enter the correct info for all those mp3 that itunes read as "track 1" "track 2" etc?
TIA
new macbook   Mac OS X (10.4.7)  
new macbook   Mac OS X (10.4.7)  

Answer 1

It sounds like the artist and track names are part of the file name and your Windows player was grabbing that info from the track names. iTunes does not use file names to supply such information and instead uses standard internal tags to hold this information and when you imported the tracks into iTunes it supplied some default info. You will need to edit the tags using a tag editor, such as the one built into iTunes or an external one such as can be found on VersionTracker.
Gracenote lookups can only be done on tracks and albums that were directly imported by iTunes from the original CD. Importing music files from any other source cannot be looked up.
If you still have access to a Windows machine, you could try running the files through MusicBrainz using Magic MP3 Tagger. I have not had much luck identifying taggless or unknown songs using iEatBrainz for the Mac (these programs are available on MusicBrainz).
There are some scripts in the Managing Track Info section of Doug's AppleScripts for iTunes that will copy filenames to track tags that can automate converting filenames to tags, but there are limitations on what can be done and you will still need to manually clean up the data and to add tags that cannot be added using such a script.