Yes, you certainly can. You need at least 256MB's of ram to do it, you also have to do all the updates to the firmware also on 9 before you upgrade. You can find old OS X CD's for sale, around various places around the internet. But guessing you have a G3 iMac, get the CD's of 10.3 then upgrade to 10.3.9. I personally got a iMac G3 350MHz with 256MB and OS X 10.2 with classic installed. I found CD's of 10.3 installed it, and deleted OS 9 because I don't like OS 9 at all. I attempted to install a bigger HD, but I couldn't get the case open... Hope that helps and good luck to you.