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I would think it's the headphones. Most stereo jacks only make connection with the plug on one side, using pressure to get a good conductivity. If the plug end was bent then the pressure exerted by the jack would make the plug rotate to the side. The plug would then be in very light contact with the jack, if at all.
On an 1/8" plug the tip is used for the left channel and the middle for right. This is probably why the left isn't working.
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