System and method of providing advertisements to portable communication devices

A system, comprising:

• at least one wireless communication access point deployed along a freeway;
• a database coupled to the server, the database storing one or more media files associated with one or more advertisements, the database storing information concerning the types of media files supported by one or more portable communication devices;
• a server coupled to the database and having access to the at least one wireless communication access point, the server comprising:
• a processor;
• a computer readable medium accessible to the processor;
• and
• a computer program embedded within the computer readable medium, the computer program comprising:
• instructions to monitor the location of the one or more portable communication devices in communication with a data network as the one or more portable communication devices travel within a user vehicle along a freeway;
• instructions to determine the one or more types of media files supported by the one or more portable communication devices;
• and
• instructions to transmit one or more advertisements to the one or more portable communication devices, based on the location of the one or more portable communication devices and the one or more types of media files supported by the one or more portable communication devices.

A server, comprising:

• a processor;
• a computer readable medium accessible to the processor;
• and
• a computer program embedded within the computer readable medium, comprising;
• instructions to monitor a location a portable communication device traveling along a freeway within a user vehicle;
• instructions to retrieve at least one advertisement from a database, the advertisement having a format based on a media file type supported by the portable communication device and based on a service tier level, wherein the media file type complies with the service tier level or a lower service tier level.