The game CliqueR is a pencil-and-paper game with a huge diversity of possible boards. This ar- ticle defines the game and establishes many of its graph-theoretic properties. These properties point toward a natural technique for classifying the strategic depth of different starting boards. A sys- tem for automatic content generation of CliqueR boards is given and use to produce illustrations of the various properties of different boards. A num- ber of variations on the game are proposed as well as possible improvements to the automatic design technique.