[TOMT][Artist/Song] Looking for singer I used to watch on youtube back in 2006-2009

Sorry this is really vague but Ive been searching for the past hour or so with no luck. A friend of mine had me watch this artist on youtube back in 2006-2009 and I remember really enjoying his music. He looked similar to Destry from those old IDEK videos and IIRC he played an acoustic guitar and it was slower music. It seemed kind of emo if that helps. I think he had blonde or brown hair but I cant be positive and if I remember right he was relatively popular on youtube with music but I cant be sure. Please Help!