HTC EVO 4G :: Music Not Coming Through Headphones

I am having a very frustrating problem with my new EVO. Playing music through headphones plugged into the 3.5mm jack is very inconsistent to say the least. When I first got the phone I could not hear music through the headphones (using the htc music app) at all. I could hear ringers, notifications, etc. just not music. I updated the software and it worked, though now I think it had nothing to with that, it was more restarting the phone.

Earlier today I plugged in the headphones and the music came through fine. The song I was listening to stopped, I went to select another song, and the music stopped working through the headphones after having worked just a second before. Again, I could hear every other sound but not the music. I turned the phone off and on again and it worked fine again. Hours later, I plug my headphones back in, and nothing. As a background, it's not he the headphones I've tried several. I can hear everything else, notifications, ringers, etc., not music. The headphones icon is present at the top.

I actually cant hear anything besides notifications through the headphones when this problem occurs including Youtube, FM Radio, Pandora, etc. Although I have manged to somehow get music to play through both the speaker and the headphones by fiddling with the headphones/speaker option in the FM Tuner. Remember when I said I could hear the ringer, notifications, etc. well, those are actually coming through both the external headset speaker and the headphones. I'm not sure if that is normal behavior but, it is strange. Either way, I can't hear music, youtube, etc. through the headphones.