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Indian Poker is the "truest test of skill there is" claimed by Leonard Steakcharmer. It is played at Ted E. Bear's Mafia-Free Playland and Casino against Leonard Steakcharmer in The Mole, the Mob, and the Meatball in Sam and Max Season One.

The game is very simple and short; both players put a card on the forehead, showing it to the other player but not seeing it themselves. They must then declare/do one of the following after seeing their opponent's cards:

  • Bet: Bet an amount of money or tokens that you have the higher card. If both player's bet, the one with the higher card wins (and it is assumed a tie if the cards are equal).
  • Fold: Don't bet you have the higher card. The game is treated as a tie if one or two of the two players bet.

Leonard has amassed 10,000,000 tokens at Ted E. Bear's Mafia-Free Playland and Casino challenging people to this game. He wins by looking at the bear head's nose (in the casino), which is reflective and shows his forehead's card. When Sam and Max put a card on the nose and make Leonard assume he has the card they put there, he will Bet when he should've folded. And since Leonard bet the duo 10,000,000 for one, he lost a fortune that Sam and Max got.

Also, there is a real-world version of Indian Poker called Blind man's Bluff.