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Hollywood Squares is based on the long-running game show and allows two players to play a celebrity and joke-filled version of Tic Tac Toe. Standard stock character models fill out most of the board, while the center square is occupied by one of four celebrities: Brad Garrett (Character), Kathy Griffin (Character), Jeffrey Tambor (Character), or Martin Mull (Character). Choosing one of them during gameplay triggers full motion video of the celebrity answering a question during an actual Hollywood Squares episode.
Players can unlock new wardrobe options for their players by winning games and bonus rounds.