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You Don't Know Jack is played out as a fictional trivia game show for one to four players (except for the Microsoft Windows and Nintendo DS versions which is for one or two players), with the goal to win the most virtual money at the end of the game. Each game uses a pre-defined set of ten questions from over seventy episodes, titled by the name of the show's fictional sponsor. Most questions are multiple choice, providing one correct and three incorrect answers, along with a 20-second timer that starts once the question has been completely presented. All players play at the same time, entering their choice of answer before the timer runs out. If a player is correct, they get a base dollar amount plus a bonus defined by how quickly they answered, while if they miss the question, they lose a similar amount of money. Failing to answer does not cost the player any money.

Each player in multiplayer games is also given a single opportunity to "screw" another player, forcing them to answer the question in a much shorter time period. If the selected player answers incorrectly or fails to answer the question, they lose money which is gained by the player using the screw. However, if the selected player answers correctly, they gain additional money taken from the player using the screw.

A typical multiple-choice question in You Don't Know Jack, waiting to be answered by all four players as listed at the bottom of the screen.

The game's trivia is based on general knowledge from several fields including science, history, and geography, combined with contemporary entertainment, celebrities, and other news items; the game, as well as the series, is often described as "high culture meets pop culture".[1] For example, one question asks the players to identify which Jennifer Aniston film title would most likely have been suited for a hypothetical romantic comedy penned by Albert Einstein about the interactions between neutrons and electrons, the answer being "He's Just Not That Into You".[2] In addition to the usual questions, each episode typically features a "DisOrDat" question. This question gives the players seven words or phrases which they have to identify as one of two possible classifications, or in some cases, both. For example, one DisOrDat series asks the players to identify terms that would be features of a Nexus One phone, Nexxus shampoo, or both.[3] In offline play, only one player plays, while other players try to steal money by getting the answer right if the main player gets it wrong. In online play, all players play the DisOrDat simultaneously. Players are also urged to look for the "Wrong Answer of the Game", which is hinted at by the show's sponsor; for example, in an episode sponsored by a baby crib company, the answer "Cat's Cradle" is the Wrong Answer of the Game. Choosing the correct Wrong Answer does not penalize the player but instead rewards them with a large monetary bonus.[3] Other questions are presented in the standard multiple choice format but use recurring concepts, such as questions based on a fortune cookie message, ones about a dream Cookie had based on a movie, or ones read through Cookie's ventriloquist dummy incorporating a speech impediment that may make the question harder to understand.[3]

After ten questions are completed, the final round of the game is always the "Jack Attack" where all players compete against each other. Prior to the round, a brief clue is shown to the players to describe a relationship that they must match, for example "BFF" (Best friends forever). The game then shows one word or phrase, and then cycles through other phrases which the players must match. If players respond to the wrong phrase, they lose money; only the first player to buzz in at the correct time wins and earns money. After seven such phrases, the total scores are added and the winner is determined.

You Don’t Know Jack

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