Many years ago there was a guy named pluggy who created a thread assembling all of the uj goddess nude pics available at the time. I'd say that's up there. Slaps dressed/undressed was solid along with the happy girls peeing.
Behind the VBulletin frontend is a database system, mostly probably MySQL. Somehow the apparently "leet" Eric Gifford managed to hack into the backend database, then overwrite all the database fields that contain post text data with that phrase. All our old posts were gone. I'm not sure what all other fields he might have corrupted, besides messing up join dates.
What I never understood is didn't (and doesn't) Hoover make and keep database backups? If not every day, once a week, once every ten days? Even if Gifford screwed up the current running database, a seven day old database backup is better than nothing. So we lose ten or a hundred posts, better than losing 20K of s.murph's valuable wisdom. MySQL comes with a backup system, a simple shell script dropped into crontab. Nothing complicated.
Not making and keeping good database backups are what killed BrainDonor's original ConfusionForums, though that was mostly the site's hosting company's fault.
I think we can safely eliminate all competition on the sad/ Tragic side of UJ history. Bultav's wife announcement on a Saturday Morning that he died the night before sent shock waves. And was bad. But nothing equaled Turtles (Turtle right?) announcement that his young daughter had what brain cancer with days to live. The morning he announced she passed away the night before, I walked away from my computer, walked out into a field and wept strongly. Never done that in my life
TomFoolery, now there's a name I haven't seen in a l-o-n-g time! Dude could create some of the worst forum drama without doing much work at all. A favorite poster of mine when I first joined. Another worthy name was MartiniMan, a true forum gentleman. And BrainDonor, before he left to make CF, and making what I think is the first 20K post, using little more than smilies to get there. Freak316, the diabetic Asian, a poster of all his own.
I think we can safely eliminate all competition on the sad/ Tragic side of UJ history.
Don't forget Coyote over in UJ/SFW. His wife logging in to post about his death. A lot of us set avatars of Wile E Coyote in our profiles in his memory. Coyote could tell you how wrong your beliefs were and how right his were, and never with even the merest hint of insult or incivility doing it. SFW isn't the same without him.