A surround sound headphone system for enhancing a wearer's listening experience by providing a surround sound speaker configuration therein. The surround sound headphone system includes a headphone assembly including a pair of earpieces each having at least two speakers. The system also includes transmitting structure for transmitting sound signals from a sound signal source to the speakers of the earpieces in a manner transmitting a separate sound signal to each of said speakers in each of the earpieces. One embodiment includes a signal cord assembly for transferring a separate sound signal to each of the speakers, and includes novel signal plug and signal jack structures.