[2] Poker Night is a computer-based Texas Hold 'Em poker simulation between the player as an unseen silent participant and four computer-controlled characters: Max of Sam & Max, Strong Bad from Homestar Runner, the Heavy from Team Fortress 2, and Tycho from Penny Arcade.

The game's backstory establishes the club as having been established in 1919 when its founder learned of an early draft of the 18th Amendment, which would have banned games and amusements in addition to alcohol; though this never came to pass, the club has existed since in secret, just in case Congress tried to set prohibition into law.

The player can win these items as Team Fortress 2 unlockable equipment only if they are the one to bust that non-player character out of the game.

[7] The characters, they decided, would be fully voiced, and would have distinctive tells and dynamic responses that would manifest themselves as the game progressed.

[6] Conners stated that the goal was to create the experience of "hanging out with their virtual buddies, shooting the breeze and playing a good game of poker".

Two of Telltale's episodic adventure series include three seasons of Sam & Max and Strong Bad's Cool Game for Attractive People based on the Homestar Runner web series; both were developed in conjunction with the original creators, Steve Purcell[8] and The Brothers Chaps,[9] respectively.

[3] Telltale always wanted to respect the original characters and worked with the individual creators and studios to improve the lines; they previously had gotten similar input from Matt Chapman for Strong Bad, while Jerry Holkins was extremely helpful to refine Tycho's character based on Telltale's draft dialog.

The game uses existing 3D models for Max, Heavy, and Strong Bad, while Tycho's is built from scratch; at the time of the game's announcement near the Penny Arcade Expo, Telltale was still working on refining Tycho's model, though it was briefly seen during their Make a Scene panel at PAX.