My first job out of college was to replace PDP-8 computers on industrial spectometers with IBM style PCs using A/D converters on the photomultiplier tubes.
I wanted to go over all that just so that you know that the clients we had were not dumb people. Most had PhD in Chemistry and the jobs analyzing the results of these machines easily made 6 figures.
The office I was in had the head of Tech support who's main job was writing the manuals, not answering calls, but he got this one....
(actual words are lost in history, but this is approx)
Customer: HI, I'm having trouble, my disk 5 won't fit into the computer.
Tech Support: Are all the disks the same size?
C: Yes
TS: What size are you using?
C: 5.25"
TS: And Disks 1-4 worked OK?
C: Yes
TS: And now you are at the point where it is saying "insert Disk 5"?
C: Yes, and it doesn't fit in the drive.
TS: One moment
*places guy on hold and turns to me and relays call*
Me: What the F...
*takes phone*
M: Can you please verify that all the disks are there? You should have X, numbered 1-X
C: Is it safe to pull the 4 out of the computer?
M: *light dawns* Yes.
C: Done. All disks are here.
M: OK, now try disk 5
C: I got an error.
M: OK good. Your machine uses a "single disk" type drive. Unfortunately, you have to remove the old disk to insert a new one. So, when it asks for disk 2, you need to remove disk 1. Understand? Put in Disk 1 again and run it.
TS: *tries very very hard to hold back laughter*
C: OK, I understand. It's working. ...
*I put call on mute and speaker phone because we are in hysterics*
C: Inserting Disk 2. Opps, removing Disk 1 first
*People are now coming from other offices because we are laughing so hard*
C: Inserting Diak 3. F*** Sorry, removing Disk 2 and inserting Diak 3.
*New arrivals now getting the joke and losing it.*
C: *continues installation, forgetting to remove at least one more, but catching himself*
TS: *shoos everyone away so he can get back on the phone - we all leave and close his door.
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The mark of a true professional, he managed to complete the call. The rest of us had the giggles for the rest of the day. For weeks all you had to do was mention "Opps, Forgot to remove it" and anyone in earshot would burst out laughing.
To this day, I wonder what kind of drive he had where he could jam 4 5.25" floppies and still be able to get them out again. And I still have no idea how the installer got to Disk five wihtout an error.
The other memorable one was the woman who kept referring to "Insert the Disk into your A Drive" as "Inserting the disk into my A-hole"