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Supertic
Supertic is a programming challenge in that it can't take advantage of the minimax ply theory (with alpha-beta pruning) two player games normally require.
Minimax theory says that what's a worst position for your opponent is a best position for you; and alpha-beta pruning prioritises branches on the move trees.
Which all works fine for chess on a Cray Mark IV or Othello on a PC.
But it won't work with a game like Supertic.
Supertic is a game similar to Tic-Tac-Toe but requiring five in a row to win.
Most people regard it as simple and easy to play but in fact it's extremely complex - especially for a computer.
An MVS assembler version of Supertic for the IBM System/370 MVS/XA appeared in the early 1980s. The game used a 10 x 10 grid and a linear one ply method.
Supertic can be played with 0-2 players. It's nearly impossible to beat the machine unless you start first and use the larger 20 x 10 grid.