I broke off the tip of a pair of headphones on a plane that had a similar orientation. Sucked both because I broke my headphones and because it meant the headphone jack on my current flight was jammed so I couldn't even stuff the freebie headphones in there. This was on like a 10 hour flight connecting to an 8 hour flight...
The freebie headphones are pretty bad on a loud plane...I need earbuds with rubber seals to block out the sound so I can hear without cranking up the volume.
I messed up my plug but fortunately it's pretty robust and I managed to bend it back into shape.
I finally caved and brought my over the ear headphones with me on my last long flight. So worth it. I hate having earbuds in for hours at a time.