a system and method for delivering interactive voice messages using a voice messaging system are disclosed . in an illustrative embodiment , the system comprises a voice messaging processor and memory containing machine readable instructions which , when executed by the processor , enable the voice messaging system to : receive an inbound call from a sender ; record an interactive voice message from the sender directed to at least one recipient ; receive a voice message retrieval request from a recipient ; play the interactive voice message for the recipient ; and initiate an interactive session with the recipient to elicit responses from the recipient regarding the interactive voice message . in one aspect of the invention , an application server is provided for generating interactive voicemails and placing the inbound call from the sender to the voice messaging processor .