An online booking system includes a computer connected to a wide-area network, the computer including a processor and a memory configured to store programming and data. An act database includes entertainment records associated with a plurality of entertainers. Programming causes the processor to receive a performance request from a talent buyer over the network, the performance request including performance request data regarding an open performance date desired to be booked. The system determines if the performance request data matches a respective entertainment record in the act database and, if so, notifies a respective entertainer associated with the selected act to contact the buyer. If the act is booked, the processor updates the act and talent buyer itinerary databases. Matching a performance request with entertainment records may include determining if an entertainer is available within a predetermined number of days of the performance date and within a predetermined distance.