A portable communication device is equipped with a media-enhanced messaging application that facilitates generating text messages that are enhanced with media having wording or other characteristics that correspond to or match at least a portion of a text message input by a user of the portable communication device. The messaging application causes the portable communication device to receive text message input and search for media matching or corresponding to at least a portion of the received text message input. Media found based on the search is merged with the received text message input and transmitted to a remote device as a media-enhanced text message. The portable communication device equipped with media-enhanced text messaging functionality provides the user with message enhancement for emotional expression, enunciation and entertainment.