The present technology relates to a reproducing device, a reproducing method, an information processing device, an information processing method, a program, and a recording medium, which are capable of reproducing an appropriate HDR video. The reproducing device of the present technology acquires reproduction management information in which a first flag indicating whether or not encoded data of a first HDR video which is mandatory when a video of a luminance range wider than a standard luminance range is included in content is included in the content and a second flag indicating whether or not encoded data of a second HDR video that is likely to be included in the content is included in the content are described. Further, the reproducing device reproduces the encoded data of the first HDR video or the encoded data of the second HDR video on the basis of the details of the first flag and the second flag and performance of a display serving as an output destination. The present technology can be applied to a Blu-ray disc player.