Well if you're just talking about regular uploading then you have to get a USB cable to hook it up to a PC (WinXP, but everyone should have that by now). If you're talking about uploading from the internet then you're very limited as the PSP browser only lets you view pages at the moment. As for getting on the internet you have to have access to a WiFi connection. If you have firmware version 2.0 then you can just use the PSP's browser there. Version 1.0 to 1.5 you can dowload a few hoembrew browsers that will do the job but not as good as the 2.0 browser. Or if you have Wipeout Pure and are familiar with how DNS addresses work you can use the browser in that game. Haven't been able to get it to work for me but maybe there's just a step I'm skipping