The present invention provides a novel head-mounted display on which a video image received through wireless communication at a predetermined frequency is displayed, a display controlling apparatus, a display controlling method, and a program. A video image receiving section (94) receives a video image from an entertainment apparatus (14) through wireless communication at a predetermined frequency. A display controlling section (96) causes the video image received through the wireless communication at the predetermined frequency to be displayed on a display section of an HMD (12) in the case where it is decided that a user mounts the HMD (12). A display controlling section (96) causes a video image acquired by using a method other than reception in the video image receiving section (94) through the wireless communication at the predetermined frequency to be displayed on the display section of the HMD (12) before the video image received by the video image receiving section (94) through the wireless communication at the predetermined frequency is caused to be displayed on the display section of the HMD (12).