The Inventory is a secret club built underneath a video game storage warehouse. It was established in 1919, after a first draft of the 18th Amendment was acquired by a group of connected gamblers. It was discovered that it could not only outlaw libations, but games and amusements that could decrease the productivity of the national workforce. Despite this never coming to pass, the club has existed since in secret, just in case Congress tried to set prohibition into law. As a newcomer, the player competes in a friendly game of Texas Hold'em Poker with Max of Sam & Max, Strong Bad fromHomestar Runner, Tycho from Penny Arcade, and the Heavy class from Team Fortress 2. The player is first greeted by Reginald Van Winslow, former captain of theScreaming Narwhal, and sidekick to Guybrush Threepwood in Tales of Monkey Island. He explains the back story of the Inventory, and raises the blinds in game.

Poker Night is a computer-based Texas Hold 'Em poker simulation between the player as an unseen participant and the four characters, Max, Tycho, The Heavy, and Strong Bad. Each player starts with a $10,000 buy-in and stays in the game until they are broke, with the goal of the player being the last player standing. The game uses no-limit betting and a gradually-increasing blind betsover the course of several rounds. Randomly, one of the four non-playable characters will not be able to front the money but will offer one of their possessions as buy-in for the game. The player can win these items as Team Fortress 2 unlockable equipment only if he or she is the one to bust that non-player character out of the game. The game keeps track of the player's statistics over the course of several games, and by completing certain objects (such as number of hands or games won) can unlock different playing card or table artwork to customize the look of the game.