You should unlock this achievement by playing any original game mode getting to the end of about stage 2 dying then you enter your name on the hi score wait for the hi score to scroll through all results and you will get the upload prompt.
However this does seem to be a little buggy and does not always unlock i had it where this failed to unlock for me. I manged to find a work around however if you delete your save from the Playstation storage menu and then playthrough the Japanese 2 player version of the game I got to the 2nd of richard roses henchmen the Native American in one credit when I then entered my name and did the upload this time it worked.