Abstract: The present invention is directed to a headphone or an earpiece that includes a cushion that advantageously allows for improved comfort, sound quality, and stability in the ear. The cushion includes an inner cavity, an ear-canal aperture and a tip portion, wherein the inner cavity of the cushion accommodates a nozzle portion of a housing within the cavity, and the axis of the inner cavity is substantially parallel to the first axis, wherein the ear-canal aperture opens toward the ear canal of the user's ear when the headphone or the earpiece is worn by the user, and wherein the tip portion engages the concha of the user's ear when the headphone or the earpiece is worn by the user, and the axis of the tip portion is not parallel to the first axis.