A telephone answering system (100) and method (200) that permits a user to immediately generate a customized playback message in response to an incoming call without having to actually answer the call. The system (100) can include a ring detector (104), a command interface (114), a controller (110) and a telephone network interface (102). In response to an incoming call, the ring detector (104) alerts the called party and causes the controller (110) to activate the command interface (114). The command interface (114) is activated for a predetermined time while the call is still ringing. While activated, the called party can select or enter a playback message. The playback message can be a pre-recorded audio message stored within the device, or a voice message spoken by the called party during the activation period. After the playback message is selected by the called party, the telephone system (100) answers the incoming call and automatically plays the customized message to the calling party.