That’s one of those old ass Macs. And by the looks of things this shirt is a shout out to a very fine video on Funny or Die, which I’m going to look up right now, so that I can give you the most relevant and accurate commentary I can muster up.
This seems to be the video in question. Not that funny, maybe ‘cuz I basically get this sort of response from IT all the time. Too close to home I tell ya.
Anyways, if you live a sheltered life away from IT folks then you might find this shirt appealing.