Prisoners' Dilemma is a game which has been and continues to be studied by people in a variety of disciplines, ranging from biology through sociology and public policy. Among its interesting characteristics are that it is a "non-zero-sum"game: the best strategy for a given player is often one that increases the payoff to one's partner as well. It has also been shown that there is no single "best" strategy: how to maximize one's own payoff depends on the strategy adopted by one's partner. Serendip uses a particular strategy (called "tit for tat") which is believed to be optimal under the widest possible set of partner strategies.
A superb introduction to Prisoners' Dilemma, including both original studies of strategies and discussion of the game's broader significance is Robert Axelrod's The Evolution of Cooperation (Basic Books, NY, 1984). A more recent popular discussion is W. Poundstone Prisoners' Dilemma Anchor Books, Doubleday, NY, 1993). Still more recent is "The Arithmetics of Mutual Help", by Martin Nowak, Robert M. May, and Karl Sigmund, in Scientific American (June, 1995, pp 76-81).
There is also a web reference at Prisoners' Dilemma, from Principia Cybernetica and a more elaborate web exploration of social interaction choices at Pat's Encounter Game.
An abbreviated textbook on game theory, including a discussion of Prisoner's Dilemna, is also available on the web.
EACH, The "Evolution of Altruistic and Cooperative Behaviors" is a modelling and curriculum project, using StarLogo.
"One Good Deed Deserves Another," is a podcast from NPR's RadioLab and Robert Axelrod.
More technical papers related to Prisoners' Dilemna:
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