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The Head Trip Game involves playing as different characters or aspects of a teenage boy named Bobby through the use of cards and storytelling elements provided to each player during gameplay. There are two ways for players to play, either competitively with four participants vying for control over their portrayal character's actions at any given time or cooperatively by having one participant portray Headmaster role in addition to other three being partakers in a semi-cooperative game setting where all the characters will be playing and each of them has different personalities which is depicted through cards.