A Digital Living Network Alliance (DLNA) system and method of providing content therein are provided. A legacy media player displays a content list for content stored in the legacy media player or in an add-in server, and when a content item is selected from the list, the legacy media player determines whether the content item is reproducible by a registered digital media renderer. If the selected content item is reproducible by the registered digital media renderer, the legacy media player transmits a reproducing request for the selected content item, and the corresponding digital media renderer receives and reproduces the selected content.