Music doesn't play out my left speaker/earphone unless I squeeze it

Basically, when I play a song on my iPod Classic, the music only plays out of my right earphone unless I squeeze the iPod and then the music will also play out the left earphone.

I regularly have to squeeze it because the left headphone will stop working after x amount of time.

The earphones work fine. I have tried plugging the ipod into my car stereo and the same thing happens ( Using the charger cable not AUX) I still have to squeeze it so that the music plays out of the left speakers.