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Description
GREETINGS, HUMAN INDIVIDUALS, OR OTHERWISE. IT IS I, THE CHESSMASTER, MASTER OF CHEEEEEESS.

My stupid joke characters are always my favorites. They're just a lot of fun to act and force onto my players as a DM. I don't care how dumb or silly they are, they're all canon. They're also the most difficult to explain outside of my friend group, but I'll try my best.

This is the Chessmaster, Master of Chess. That's his full name and he will correct you if you try to shorten it. I created him for a one-off in between chapters in my campaign as a bit of a palette cleanser. It was a grand battle between two brothers and their armies, one a heavenly white and the other blood red. Basically it was chess but with D&D combat instead of regular capturing. If I remember correctly, the pieces moved according to the earliest recorded forms from India, not modern rules, since ancient India was the theme. It was based off of one of the origin myths of chess which claimed that the game was invented by the lone survivor of the conflict to gently explain the course of battle and death of one brother to their grieving mother. All of this was presided over by our beloved "guest DM", the Chessmaster, Master of Chess. I tried to stay in character the whole time, and it was really hard, because it was all very comedic and we kept inventing personalities and slapstick scenarios for the game pieces. Combine this with the fact that the Chessmaster, Master of Chess, breaks the fourth wall, and it was just raw unfettered chaos. Lots of fun.

So okay, where the hell did this come from? You know that old sand guardian, guardian of the sand Vine? Well the internet has thoroughly broken my sense of humor, so that is still some of the funniest shit I've ever seen. Now whenever I see a character whose title is just a noun combined with an identifying adjective, I always get a chuckle out of the idea of them redundantly extending it out like that. The culmination of this is the Drake Hero's own Chessmaster, Master of Chess. He's this sort of quasi-deity who holds domain over all of Chess Space, the space in which all chess games or chess-themed stories take place in. Think Through the Looking Glass and you've got Chess Space. The Chessmaster, Master of Chess, is obsessed with chess, believing it to be the only game capable of encapsulating the entire human experience. Not that he really knows what that means. He's just sort of this shambling little weirdo who sits in his chair all day and yells all his sentences in a loud, monotone voice like a cartoon alien pretending to be a fellow hoo-man. He's the least eldritch eldritch deity you can imagine. He cannot tell the difference between a DVD player and a VHS tape, this is canon. When you win a chess match against him, he bestows unto you one of his "bountiful gifts", which others may refer to as "junk", randomly selected from the D&D trinket chart. He's just a delight. I hope I get to bust him out again sometime.

Design notes, I envisioned the Chessmaster, Master of Chess, as this weird Lovecraft-esque cultist creature in your stereotypical monk robe. Me being me, I had to extrapolate further and chess him up a bit. Going with the theme of India, his main robe is inspired by the suits worn by Mughal princes. Obviously that period is much later than the invention of chess, but I just really like the aesthetic of how they layer on top of themselves. His jewelry and leather accents, meanwhile, are more so inspired by Mayan art. The boxy shapes often found in Mesoamerica lend themselves well to the very square, geometric aesthetic I was aiming for. For the checker patterns, I actually took some inspiration from that one study where they put a cuttlefish over a chess board to see if it could mimic the colors. I think it looks a little more unique than if I had just gone with squares. I wasn't quite happy with the end result at first, but it's grown on me since. Thankfully it's very easy to please the Chessmaster, Master of Chess.

Description
GREETINGS, HUMAN INDIVIDUALS, OR OTHERWISE. IT IS I, THE CHESSMASTER, MASTER OF CHEEEEEESS.

My stupid joke characters are always my favorites. They're just a lot of fun to act and force onto my players as a DM. I don't care how dumb or silly they are, they're all canon. They're also the most difficult to explain outside of my friend group, but I'll try my best.

This is the Chessmaster, Master of Chess. That's his full name and he will correct you if you try to shorten it. I created him for a one-off in between chapters in my campaign as a bit of a palette cleanser. It was a grand battle between two brothers and their armies, one a heavenly white and the other blood red. Basically it was chess but with D&D combat instead of regular capturing. If I remember correctly, the pieces moved according to the earliest recorded forms from India, not modern rules, since ancient India was the theme. It was based off of one of the origin myths of chess which claimed that the game was invented by the lone survivor of the conflict to gently explain the course of battle and death of one brother to their grieving mother. All of this was presided over by our beloved "guest DM", the Chessmaster, Master of Chess. I tried to stay in character the whole time, and it was really hard, because it was all very comedic and we kept inventing personalities and slapstick scenarios for the game pieces. Combine this with the fact that the Chessmaster, Master of Chess, breaks the fourth wall, and it was just raw unfettered chaos. Lots of fun.

So okay, where the hell did this come from? You know that old sand guardian, guardian of the sand Vine? Well the internet has thoroughly broken my sense of humor, so that is still some of the funniest shit I've ever seen. Now whenever I see a character whose title is just a noun combined with an identifying adjective, I always get a chuckle out of the idea of them redundantly extending it out like that. The culmination of this is the Drake Hero's own Chessmaster, Master of Chess. He's this sort of quasi-deity who holds domain over all of Chess Space, the space in which all chess games or chess-themed stories take place in. Think Through the Looking Glass and you've got Chess Space. The Chessmaster, Master of Chess, is obsessed with chess, believing it to be the only game capable of encapsulating the entire human experience. Not that he really knows what that means. He's just sort of this shambling little weirdo who sits in his chair all day and yells all his sentences in a loud, monotone voice like a cartoon alien pretending to be a fellow hoo-man. He's the least eldritch eldritch deity you can imagine. He cannot tell the difference between a DVD player and a VHS tape, this is canon. When you win a chess match against him, he bestows unto you one of his "bountiful gifts", which others may refer to as "junk", randomly selected from the D&D trinket chart. He's just a delight. I hope I get to bust him out again sometime.

Design notes, I envisioned the Chessmaster, Master of Chess, as this weird Lovecraft-esque cultist creature in your stereotypical monk robe. Me being me, I had to extrapolate further and chess him up a bit. Going with the theme of India, his main robe is inspired by the suits worn by Mughal princes. Obviously that period is much later than the invention of chess, but I just really like the aesthetic of how they layer on top of themselves. His jewelry and leather accents, meanwhile, are more so inspired by Mayan art. The boxy shapes often found in Mesoamerica lend themselves well to the very square, geometric aesthetic I was aiming for. For the checker patterns, I actually took some inspiration from that one study where they put a cuttlefish over a chess board to see if it could mimic the colors. I think it looks a little more unique than if I had just gone with squares. I wasn't quite happy with the end result at first, but it's grown on me since. Thankfully it's very easy to please the Chessmaster, Master of Chess.