The improved resilient flexible headrest of the present invention is inflated with air or fluid, or is filled with foamed plastic material, preferably of various resiliencies. The headrest can be formed of plastic, cloth or the like, and has a cavity within which the upper end of the backrest of a chair, couch or the like is receivable. The headrest includes means for securing the headrest in place to the backrest, preferably releasably. The body of the headrest may be structurally reinforced with stiffining elements and preferably has forwardly extending privacy wings which may be hinged and which include sound system speakers or the like. Alternately, the wings may be bridged by a privacy roof. The roof may have an eye shield such as a cloth or the like attached thereto and lowerable from the front thereof. A pocket with a transparent outer facing may be disposed on the outer surface of the body of the headrest to releasably receive a ticket, advertising indicia or the like. In one embodiment, the headrest may be U-shaped in plan view and include one or more straps and cinch means to releasably hold the headrest in place around the top of a backrest. The wing can be contoured to provide a lower, inwardly extending portion to better support the head and/or retain a pillow in place.