Can't open songs because it can't find files that are where they should be

For about 90% of my Itunes library, when I try to play a song it says it can't be opened because the file can't be found. I can find the file and it's exactly where it should be and once I find it, it plays fine. These are not new songs, but one's I've had in the library a long time. It's pointing correctly to the Itunes music folder, but only seems to be able to find stuff that I fairly recently added. Can anyone help?

It is likely that something has been moved. iTunes does not do folder watching so if anything moves or is renamed iTunes will not find it.
If you open iTunes Music Library.xml with WordPad, you can see where iTunes thinks your music files are located.
Look for Lines starting <Location>, note the the space character is represented by %20 in the path.
You can look for specific files with Find.
This may help you to workout what has gone wrong. Whether or not this leads to an easy solution is less certain. If the files are not where iTunes thinks they should be, and moving them so that the path is correct is one possibility if it can easily be done. The other is to use Find and replace to correct the paths if there is an easy edit that can be done. Then recreate the library from the xml file as in this article.
http://support.apple.com/kb/HT1451
The third possibility that is easy and certain to work is to start with a new library. But this loses all counts ratings and playlists.
Close iTunes, drag iTunes Library.itl and iTunes Music library.xml out of the iTunes folder to the desktop.
Open iTunes and an empty library is created. Use File>>Add folder to library... to add you iTunes Music folder.

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