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Since I was a child, I was intrigued by two similar apparent inside jokes that I never understood:

I would consider armed postmen an absurdity, but why postmen in two completely unrelated jokes? Was there some public debate about armed postmen at some point? Are they even armed under some circumstances?

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"Going Postal" became a meme 20+ years ago for aggressive or violent behaviour...

From Wikipedia

Going Postal

The expression derives from a series of incidents from 1986 onward in which United States Postal Service (USPS) workers shot and killed managers, fellow workers, and members of the police or general public in acts of mass murder. Between 1970 and 1997, more than 40 people were killed by current or former employees in at least 20 incidents of workplace rage.

No, USPS employees are not armed and it should be noted that..

The [US] Post Office has been a “gun-free zone” since 1972 when Congress enacted the ban after a string of postal work-place shootings. In each of the 6 major shootings, it was not the average citizen that went on the rampage, but rather the Post Office’s past and present disgruntled employees! This is where the phrase “going postal” came from.

Opinionated Source

Indeed, the clip from The Naked Gun they are specifically referred to as "disgruntled postal workers" and are just another piled on threat Frank Drebin is facing...

I would suggest that the "joke" in the Simpsons is that the last person one would expect to be armed is a Postman.

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  • For the Simpsons joke, it could be the same joke as for the Naked Gun; i.e. the joke isn't that a postman is the last person you'd expect to have gun, but rather the most likely person to carry a gun for a reason that's unrelated to the current scene. Similarly, if a prostitute gives a pair of handcuffs to a cop, the joke isnt that a prostitute is the last person who'd have handcuffs, but rather than they are likely to have handcuffs, just for a different reason than usual (adult games vs arresting criminals).
    – Flater
    Oct 23, 2017 at 9:39

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