An entertainment apparatus, a display controlling method and a display controlling program are provided which are capable of presenting a compatibility situation of a program or content with VR display to a user without relying upon representation by a selection target itself from which the program or the content can be identified. A compatibility situation data acquisition unit acquires compatibility situation data indicative of a compatibility situation with virtual reality display of the programs or the content upon selection by the user, the compatibility situation data being different from the selection targets. A screen image generation unit generates, on the basis of the compatibility situation data, the screen image including information indicative of a compatibility situation with virtual reality display of the program to be executed or the content to be reproduced in response to selection from the selection targets. A display controlling unit causes the screen image to be displayed.