In one implementation a method of transmitting a file having an advertising portion and a requested portion different from the advertising portion is provided. The method includes receiving a request to transmit the file, via a streaming protocol allowing non-sequential access, transmitting the advertising portion of the file, receiving a request to transmit a portion of the requested portion of the file prior to completing transmitting the advertising portion of the file, completing the transmission of the advertising portion of the file, and transmitting the requested portion of the file. In another implementation a method of transmitting streaming data from a server to the data storage medium of a device having a multimedia player is provided. The streaming data having at least one advertising-sponsored content portion and at least one associated obligatory advertising portion. Upon the server determining that the playing of all or part of the obligatory advertising portion is attempting to be avoided by the multimedia player, the server sends to the multimedia player or device a message with data storage medium control information for the purpose of inhibiting the advertising-sponsored content portion stored in the data storage medium from being played by multimedia player.