If you've been running Linux for a while, you may have seen libcaca get pulled in as a dependency here or there and thought it had a funny name. It is a library for manipulating text graphics ("ASCII Art," though it has full UTF-8 support). I visited their website this morning and thought it was remarkably quaint.

Also got a big laugh out of "Terror on the Desktop."

spoiler

hot-babe was a CPU usage monitor for X11 displays which embedded in your desktop in a similar fashion to conkey. It featured an anime waifu who would get increasingly naked the more busy your computer was. A utility which now lives in the trash heap of computer history.