On April 1, 2013, Telltale officially announced a sequel, titled Poker Night 2, featuring Brock Samson from The Venture Bros., Claptrap from the Borderlands series, Ash Williams from The Evil Dead franchise, and Sam from Sam & Max as opponents. The characters are also written to be somewhat cognizant of their nature according to Rodkin, Tycho and Strong Bad are aware of their video game nature, while Max is ambiguous and the Heavy remains blissfully unaware of his death-and-respawning cycle, simply attributing his memories of dying over and over again as dreams. The developers also wanted to avoid any forced interactions, and instead developed what they felt were natural relationships: Tycho dislikes Strong Bad while getting along well with Max, while the Heavy looks upon Strong Bad as a tiny Heavy. 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. To that end, they created a large amount of dialog for each character and possible interactions between the characters according to Jake Rodkin, Telltale's graphic designer, they wrote more lines of dialog for the game than a typical Sam & Max adventure episode. Telltale aimed to make the game dialog-centric between the four featured characters.

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