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I have come across it in the 10th episode of the 7th season of The Office. Here is the context:

Jim: Woah, there is a lot of brainpower in this room. We’ve got Michael and Oscar, the two smartest guys in the office, also in that order.

Oscar: Funny Jim. That is funny.

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  • Around here Oscar is known as "actually"... Jim is teasing him about not being the smartest guy in the office Jan 16 at 16:12
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    They're specified in the sequence Michael first, then Oscar, and we're told these two are the smartest people in the office. Since it's reasonable to assume Jim would have identified the smarter of those two FIRST if there was any significant difference on that front, we can further assume that in that order is intended to confirm that Jim really did deliberately name Michael first because Michael is the smartest. But this isn't really to do with English - it's just a matter of logic. Jan 16 at 17:54
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OK so I think it needs a bit more context, so I watched a clip of the scene, and I think it takes place after Michael has beaten Oscar in some kind of "who's the smartest" competition? So what Jim's saying is that Michael is smarter than Oscar, because they're the two smartest "in that order", the order he said their names in.

I think it's a dig at Oscar losing the competition when presumably Oscar is considered smarter than Michael, and also a dig at Michael because he thinks Jim is being sincere, which he isn't given Jim's disdain for Michael.

There's clearly a lot of context and nuance, but taken literally he's saying that Michael and Oscar are the smartest guys in the office, and that Michael is smarter than Oscar.

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"That order" is Michael first and Oscar second.

He is talking about being smart, so it means that Michael is smarter than Oscar. It is a subtle insult to Oscar. Probably the whole exchange is ironic.

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