A system and method for providing enhanced audio messaging services. The system comprises a voice gateway for interfacing with a plurality of telephone devices, a voice messaging server (VMS) and a content server that together enable the execution of the enhanced messaging services. The system further includes a metadata database for maintaining metadata associated with users, messages and content items. The enhanced audio messaging services include, but are not limited to, phone-to-phone sharing of audio content, phone-to-phone sharing of broadcasted radio content, web-to-phone audio content sharing, phone-to-web content sharing, interactive group discussions, and dynamic asynchronous audio messaging.