WHY the nipple at all?? Just bring the NM into the back of the box. Make sure to seal around the box really well.
Broadly speaking, there needs to be SOME sort of chafe protection and strain relief, to be legitimate. I assume you mean to use a connector of some sort. The OP might not understand that if you are not explicit.
If the box is some sort of cast Bell box with threaded holes, a chase nipple could be screwed in and that would resolve the chafe requirement. A staple to framing within 8" would give you strain relief, I suppose. This would permit a pretty discrete hole in the wall.
Are we talking about what is safe, or what is perfectly to code? I am sure there are inspectors who would OK the above, and others who would flag it.
Heck, if the hole in the wall is big enough for a metal connector with a screwed down strap to grab the NM, then all is good, your point to seal the hole in the wall is the necessary cherry on the sundae.