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safe2272329 artist:elslowmo279 artist:late15 princess luna121947 twilight sparkle371931 pony1705321 g42131066 armor33121 chess529 chess with death4 costume41924 crossover75477 death6393 female1914525 levitation17168 magic102198 mare809494 parody17769 reference5887 sitting100493 sword15524 telekinesis41455 the seventh seal10 weapon43615

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Background Pony #BD43
Personally, I would play croquet in a put put golf place. That should last weeks and turn it into a battle of attrition.
Background Pony #BE64
“Ah rememburr as ah littul bui bah the seeside, it wus ah gaime an’ ah gnu ah had vune.”
Ghouleh
The End wasn't The End - Found a new home after the great exodus of 2012

Awww, man… From the thumbnail, I thought it was a Dune crossover, with Twilight wearing a stillsuit and Luna as a Bene Gesserit.
 
Still, this is good enough as it is.
Background Pony #3043
@ROTHY  
Personally, I’d choose tic-tac-toe. First to win 1 game wins. I would literally be immortal.
Background Pony #1089
These days:“I am Death. Your life is at an en…dude, is that the new Halo?”
Prof.NightJack
Equality - In our state, we do not stand out.
The End wasn't The End - Found a new home after the great exodus of 2012

Gizmonics Scientist
@ROTHY  
Billy and Mandy played limbo and the Warner siblings played checkers(and it was Death that pick chess in the first place, they didn’t know how to play), so not everyone play him at chess.
Background Pony #1089
Of course, Death is under no obligation to play. In the movie this picture parodies, the guy was lucky that Death was chill enough to honor his request for a game. Which was greatly helped by that fact that Death actually liked to play chess.
Psychopomf
The End wasn't The End - Found a new home after the great exodus of 2012

It would be awkward if Princess Luna was also the pony reaper
 
“Oh hey Luna. Are you here for a visit?”
 
“Nay Twilight. You must come with us.”
 
“When will we get back?”
 
“About that…”
ROTHY
The End wasn't The End - Found a new home after the great exodus of 2012

Why does everyone pick chess to save their soul? Death has obviously perfected his chess game over the years because it’s the one everyone chooses, so why not play something that he’s unfamiliar with, like Risk?