I used to do billing support, which doesn't give you quite as many stupid-user stories, but I had a few.
My favorite was a nasty elderly woman who called up after we switched HBO from an analog signal (no box needed) to a digital signal (box needed.) She berated me for a good five minutes about how the company was money grubbing, but the best part was when she screamed she was going to sue us for not notifying her:
"I'm sorry ma'am, we sent out letters two months before the change happened, I apologize you didn't receive yours."
"I throw out anything that's not a bill!"
"We also put it in the news section on the bill, in the left-hand column last month."
"I don't read my bills, I just pay them! I've paid every month on time for as long as I've been a customer!" [Checks billing history, sees customer has been 30 days late over a dozen times, and 60 days late three times.]
At this point, I decided to see what else she was lying about, so I pulled up her call history (a log of every time the customer calls us and every time we call the customer.) I was on a team that personally called every single one of the thousands of customers affected (most had already undergone the change years ago,) and guess what? Dated, timestamped, and noted--"Called customer to inform of change, halfway through intro customer screamed never to call her again and hung up on me. Sub already on do-not-call and do-not-mail lists."
And the best part? I was the one who called her.
Second place would be the guy I spent 15 minutes with trying to get his online billing system working. The guy had forgotten his password, and was screaming at me that our system was a POS, that he was leaving us for DirecTV, that we were a bunch of thieves, and that our entire department was useless. We were stuck on the point where he had to answer his security question to reset his password:
"I know where I met my goddamned wife! We were at the gift shop at the Jacob Javits Center! I've tried gift shop, javits, javits center, lower case and uppercase and everything! The goddamned system is broken!"
[Hazzarded a guess and put in Javits Center on my screen to see what would happen.]
"Well, let's try one last combination--try J-a-v-i-t-s--"
"Oh."
"Sir?"
"Well, I told you I knew where I met my wife, I just can't spell."
I could go on with these forever now that I got started, but a perennial favorite was our AmEx users. Far and away, more people signed up for recurring, automatic bill payment through AmEx than through Visa, Mastercard, and Discover combined. People would then proceed to forget about their cable bill for years, until they finally received a late notice.
"What do you mean the card was rejected! I've been using that card since before you were born!"
"Well, from what I see on the account sir, it looks like the card expired last month, at which time the payment was rejected, and our system sent you an automatic notice to update your card information."
"It wasn't rejected! I've had this card since before plastic was invented!"
"I do apologize sir, but my screen shows your card expired. Is it possible that AmEx has sent you a new card in the last month or two."
"Of course, BUT IT'S GOT THE SAME NUMBER!"
[Puts headset on mute, strangles stress toy, breathes a large sigh.]