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One, two, or three players can play the game. The premise of You Don't Know Jack is similar to that of a TV quiz show: players compete for money by answering trivia questions. (Since this is not a real quiz show, however, players do not win real money.) All versions of the game have an off-screen "host" who is voiced by a Jellyvision staff member and referred to by his nickname -- "Cookie" and "Schmitty" are the two most common in the series.
Most versions of YDKJ offer the choice of playing a 7- or 21-question game; some versions offer only 15 questions. In a 21-question game, there is a brief intermission after the tenth question.
In most versions, a randomly-chosen player is given a choice of three different categories. Each category has a humorous name that vaguely describes what that question is about. After a short animated introduction (often accompanied with a jingle about the question number), the host asks the question. The first player to buzz in with the correct answer -- using their specified buzzer key on the keyboard -- wins the money for that question and gets to choose the next category. Players lose money with an incorrect guess like they would on Jeopardy!, but not before the host wisecracks about it. (One running gag in the series relates to questions about The Facts of Life: " Tootie" is never a correct answer.)
In most versions, the more difficult questions are worth more money. Two versions (The Ride and 5th Dementia) allow players to buzz in before the question to determine how much it is worth.
In multi-player games, players have the opportunity to "screw" their opponents by buzzing in, typing "S," and selecting one of his or her opponents. That player is then forced to give an answer within ten seconds. If the player who is "screwed" answers correctly, he or she wins the money while the player who "screwed" him or her loses money. Players are only allowed to "screw" once in each half of the game (they each receive a new "screw" in the second half of a 21-question game).
The majority of You Don't Know Jack questions are multiple-choice, with four possible choices. Some questions are fill-in-the-blank, requiring a typed response.
Special questions are also played during the game. Each version of YDKJ has its own different types of special questions, but the two most common are:
The last question of each game is known as the "Jack Attack," which is a word association question. A clue is given, and after that a word, phrase, or name that fits the category of that clue appears in the middle of the screen. After that a series of potential matches appears on the screen; each potential match appears for only a few seconds before disappearing.
Players win money if they buzz in when the correct match is displayed on the screen; the match must fit the clue that is given at the beginning of the Jack Attack. An incorrect guess at any time -- even if that player already buzzed in for the same word -- deducts money from the player's score.
The winner of the game is crowned after the seventh Jack Attack match.