Hello,
OK.
Please note the difference between booting the computer from Mac OS 9.x.x and using Mac OS 9.x.x under the Classic environment (Classic starts under Mac OS X).
Because of the operating systems involved, I guess it would be correct to assume that this is one of the iBook G3 models, so both ways should be possible.
For printing from the Classic environment, see the article http://support.apple.com/en-us/HT3147 to begin with.
Any luck? Otherwise, and if applicable, you may want to test booting the computer from Mac OS 9.x.x (select system in Startup Disk under System Preferences) and try the Chooser and any existing Chooser extension/driver from there.
Anyway, before you do anything, please make sure that you have backup copies (for example, on USB flash drives or CDs) of your important documents.
Yes, you should be able to print from Mac OS X as well. It depends a bit upon the type of document, but do check whether your Mac OS X programs can open the files (look through the Open dialogues for supported file formats). Sometimes, one can re-save a document in another suitable format (via the Save As dialogue in a Mac OS 9.x.x program) in order to make things easier.
Yet another way could be to transform a document into a PDF file under Mac OS 9.x.x, and then print from Mac OS X.
Jan