This one happened to my manager, but we trade stories of stupid customers all the time.

Her: Thank you for calling the Goodwill, how may I help you?
Caller: Can I rummage through the dumpster there? I hear that you guys have the best stuff in there.
Her: I can't authorize you to do something like that.
Caller: Oh, I wasn't asking for permission.
Her: Why are you calling?

When I worked at a wine store:

Guy: What's the cheapest wine you sell?
Me: Uh... this one here. (five litre goon bag)
Guy: Thanks, I'll take three.
Me: No worries.
Guy: I'm an alcoholic. I'll be back for more tomorrow!

Me: "What version of Windows are you running?"
Them: "Hold on, let me check."
Me: ??
Them: "They're thermal."
Me: "I...I beg your pardon?"
Them: "The windows are thermal."
Me: "..."

The Chick-Fil-A near me has the nicest, friendliest, fastest fast food workers I've ever met in my life, maybe because they've only been open for 10 months or so and nobody there has had the chance to get jaded and cynical yet. I'll share a story from Chick-Fil-A myself, even though I don't work there.

I was in the drive through one day, and it was still warm outside so I had my window down and could hear the car in front of me place his order, not in these exact words, but the important parts are still here.

Speaker (male): Thanks for choosing Chick-Fil-A how can I help you?
Guy in car: I'd like a (bunch of food)
Speaker (still male): Anything else?
Guy (turns to his wife in car): Oh! and a potato please.
Speaker (confused male): You mean an order of waffle fries?
Guy: No! A potato!
Speaker (male): Waffle fries?
Speaker (female): Sir, can I help you? What was it you wanted?
Speaker (female): Waffle fries, sir?
Guy: Yes. (turns to wife, then back to speaker) I mean NO, A POTATO!

This went on for a couple minutes during which the voice on the speaker changed at least two more times, till they finally told him to just pull around. Since my order is simple (#1, Coke) I got around quickly and was able to see him at the window and see them actually thrust an order of waffle fries out the window at him, have him nod his head happily, take them and drive off.

When I pulled up, they asked me something to the effect of what condiments or whatever I wanted, and this was my response (yes I did actually say this to them).

Female at window (paraphrased): Condiments?
Me: Can I get a potato?

A lot of them were gathered around the window, likely due to the idiot in front of me, and the whole place busted up laughing. They were shocked that I had heard him, and I told them it was likely the whole county had heard him shouting POTATO! at them at the speaker.

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