Oh man, I used to work as essentially help desk for old people where they were subscribers to unlimited remote support and we would screen share. I once watched someone, whose browser homepage was hijacked by Yahoo, type Google into Yahoo, click the first result (to Google), then they typed Gmail into the Google search, clicked the link, and finally got to Gmail to login.

Still not as bad as the lady who insisted on hacking Farmville using scripts and Firefox extensions that would have to call us every few weeks to fix everything due to an update. We essentially had to update Firefox and extensions and scripts and reload it all very often. She got passed around a lot.

Then there was the guy who we helped low key pirate media, he was fun. Super nice guy.