Here is the full list of all 18 Poker Night 2 achievements. It takes around 15-20 hours to unlock all of the achievements on Windows.
Win GLaDOS's bounty item.
Win Claptrap's bounty item.
Activate the Portal deck, felt, and chips simultaneously.
Unlock all decks, felts, and chips.
Achieve a lifetime balance of one million dollars.
Activate the Army of Darkness deck, felt, and chips simultaneously.
Win Brock's bounty item.
Win Sam's bounty item.
Activate the Venture Brothers deck, felt, and chips simultaneously.
Activate the Sam & Max deck, felt, and chips simultaneously.
Activate the Borderlands deck, felt, and chips simultaneously.
Win Ash's bounty item.
Purchase a drink.
Purchase a felt.
Purchase a deck.
Purchase a set of chips.
Win a tournament.
Win a hand.