First appeared in the original Sam and Max comics. In Season 3, Max uses his psychic powers to prevent Flint from getting murdered.
Poker Night At The Inventory
Cameos in Poker Night at The Inventory, sitting at the bar with a drink, and is the "hero" of many of Max's stories, which usually involve beating the player character from Telltale's previous poker game, Artie Flopshark, into a pulp for doing things like raising money for charity and teaching the "fake" poker variant Omaha.
When Tycho gets knocked out, he sits at the bar next to Flint. Max's stories impress Heavy, who approves of Flint's violent behavior.