IMHO, for the finest vintage computer/sysadmin nightmare humour, one cannot do better than Simon Travaglia's classic 90's 'B##tard Operator From Hell' series, portraying the "alternate-world Simon the Sysadmin who would torture and ruin his users in the pursuit of more free time and lager."
Please Note: These articles contain mild cursing, most notably the edited B word used in the title above and occasionally a couple of others like the edited P word below that are used for colour. That's as strong as the language in this series gets. If that doesn't put you off, the articles are hilarious. I enclose a sample from article #1 below.
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Another user rings.
"I need more space" he says
"Well, why not move to Texas?" I ask
"No, on my account, stupid."
Stupid? Uh-Oh.
"I'm terribly sorry" I say, in a polite manner equal to that of Jimmy Stewart in a Weekend Family Matinee Feature "I didn't quite catch that. What was it that you said?"
I smell the fear coming down the line at me, but it's too late, he's a goner and he knows it.
"Um, I said what I wanted was more space on my account, *please*"
"Sure, hang on."
I hear him gasp his relief even though he'd covered the mouthpiece.
"There, you've got *plenty* of space now!"
"How much have I got?" he simps.
Now this *REALLY* *PI##ES* *ME* *OFF*! Not only do they want me to give them extra space, they want to check it, then correct me if I don't give them enough! They should be happy with what I give them *and that's it*!
Back into Jimmy Stewart mode.
"Well, let's see, you have 4 Meg available."
"Wow! Eight Meg in total, thanks!" he says, pleased with his bargaining power.
"No" I interrupt, savouring this like a fine red at room temperature, with steak, extra rare, to follow; "4 Meg in total.."
"Huh? I'd used 4 Meg already, How could I have 4 Meg Available?"
I say nothing. It'll come to him.
"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaagggggghhhhhH!"
I kill me, I really do!
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for the full series .....
http://bofh.ntk.net/BOFH/index.php