A system and methods for facilitation of enhanced user interactions with metadata corresponding to one or more media files. A number of user interface methods are described and may be used alone or in combination with one another to present an enhanced metadata entry and modification interface to a user. A method of providing for automated step through of media files for metadata entry is described, as well as a method for quickly presenting the user with the most appropriate media sample from which an appropriate metadata entry or modification can be made by the user.