Pontoon is the CUTwC variant of the common card game, also known as blackjack of twenty-one. One could argue that in most versions of Pontoon, it is a good thing to be the dealer. In the CUTwC version, not so much.

In the CUTwC version, the dealer provides each player (including himself) with a card, face down. The players look at that card, put it face-down on the table, and then place a number of fingers from one to four on the card, indicating the amount they are willing to risk on whether they are likely to beat the dealer. A second card is then dealt face-down to each player, again including the dealer.

With the aim of getting a total nearer to, but not over, 21 than the dealer does, each player in turn is offered the chance to "stick" (receive no more cards), "twist" (be given a card face-up, such that everyone can see the card) or "buy" (be given a card face-down so that only the player sees the card, and increasing the bid by one) additional cards - one cannot buy once one has twisted, but one can buy and then twist. Most cards have their numerical value; face cards are worth ten, and aces are worth a choice of one or eleven.

A player who has an ace plus a ten or face card in the first two cards must demonstrate this when it is there turn by turning over their non-ace card - a pontoon beats any other hand (CUTwC does not treat three sevens as special, nor does it make a distinction between a numerical or royal pontoon). A "five card trick" (five cards less than or equal to 21) beats any other hand. If the two cards in a player's hand are identical, the player has the option to split, and be given two additional cards (this can be done repeatedly, but only with the two initial cards); the player then gets to play multiple hands, each with the initial bid placed on it.

If a player "goes bust" (has a total more than 21) he must say so immediately and return his cards to the dealer, who should place them on the bottom of the pack. One does not shuffle in Pontoon.

When each player has got to the point of sticking or going bust, the dealer gets to play. The dealer is playing against the players still present, and can make intelligent decisions (rather than applying fixed rules as in a casino). The dealer may not split. When the dealer's hand is finished, the dealer drinks for every finger bid by the players who beat him, and the players drink for every finger they bid if they lose. If there is a tie, the dealer wins. If the winning hand is a pontoon, the amount drunk by the dealer doubles. If the dealer goes bust, any player who has not also gone bust wins, and the dealer drinks their bids. For obvious reasons, the deal rotates. It is considered bad form for the person who is about to be dealer to propose a change of game.