Half of the time logo is missing from cable or flash drive (especially designer drives). Another problem is not everyone is using laptops even today, and that meme is originating from the times when laptops were much more rare and less usable. In the PC you just don't see whatever happens in the back when you are plugging in cables, especially since most of the time ports are vertical.

And the meme itself comes probably from the fact that USB-A port needs rather precise positioning to connect. Even if you are inserting connector the right way from the start, you will most likely hit metal part of the connector against metal parts of the port at first try and it will cause you to doubt yourself. You then turn it (incorrectly) and fail again, turn again (correct now) and try connecting more slowly and precisely and only then it fits :)