An information processing apparatus for reproducing second content in synchronization with reproduction of first content by a second information processing apparatus different from the information processing apparatus, the first content comprising audio content. The information processing apparatus comprising circuitry configured to: extract a first feature from the audio content; obtain a second feature of the audio content, the second feature being together with the second content; compare the first feature with the second feature; and generate, based on results of the comparing, synchronization information used for reproducing the second content in synchronization with the first content.