Debian security motivational posers
Software
I got a kick out of these tounge in cheek Motivational Posters that take at jab at Debian GNU/Linux for their embarrassingly severe low entropy security hole in their implementation of OpenSSH in May 2008.
I remember seeing some funny FreeBSD Motivational Posters at some point recently too that asseted that FreeBSD users are reliable but boring (I'm a FreeBSD guy of course!), but for the life of me I can't remember where. You'll all be the first to know when I do, even though I'm not Bill Kurtis.