My wilson mp3 player (the cheap $50 ones with the one big play button on front) It doesnt play on the right side of headphones. Well i tried this with many headphones...but the only way it work is if I push the the headphones in hard and push it upwards. I guess its not making contact with something and when I push up it makes contact. Anyone else have this issue or know a fix?

if you can take it apart without destroying it, it is very probable that the solder connection for the headphone jack is broken or cracked.

if you are skilled at soldering, you might easily re-solder it.