Would be simple enough using a plugin, a script, or just a bunch of curl commands, however I think it would be better to pressure Atlassian into supporting a gravatar-like service JRA-24653, as Fisheye already does.
Otherwise it's a constant pain to keep the pictures uptodate, and deal with the fact that users can upload their own picture which you probably would not want to overwrite, etc etc.
EDIT: I just saw you tagged confluence, but I believe my comments equally apply to jira and confluence.
Just to clarify your question...Do you want to upload the same picture to use for all users at the same time?
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