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Finding and conversing with the Shadowman in his prison cell is NOT enough. To "defeat" the Shadowman, you have to pick specific dialogue options.
You only get one chance, or you will have to start the ENTIRE game over again to get another chance at this achievement.
I didn't know exactly how to get this trophy in my playthrough on PS5. It's the only trophy I need for the platinum, but that would require replaying 90% of the game again. This is a long game with a lot of sections of slow walking and tedious combat encounters. I estimate it'd take a minimum of 6-7 hours to get back to the Sixtopia prison, skipping all sidequests and cutscenes. Not worth it!
Please look up a video on YT for the correct dialogue options to pick.
Calling him pathetic in short by striking his ego.
Using other lines won't unlock the achievement.
Game Master - Cost: 0 (FREE)
Description: Move the Game Piece 1 tile forwards. Draw a new card.
So why is this good, nigh broken? First of all, it helps get through the board game sections a bit easier, moving 1 additional tile is the difference between stopping at a wall and waiting for another dice roll to clear it or just finishing the event.
But the real broken thing is it still draws to replace itself if it isn't doing this with that second part.
Since the card is free to play from hand, and draws a new one from your deck - This effectively lowers your deck's size by X where X is the amount of Game Master cards you have in your deck, and in turn makes drawing your better cards much faster.
Also fun synergy of a combo is Bloob + Crystal Shattering = Damage. Faster than a bomb and more long lasting.