To me they had a similar feel and atmosphere. The two movies are very different in terms of subject matter and story in general (also how to win at checkers doesnt include straight up homophobic characters). They crush you, both are dramatic bur have some nice moments sprinkled in between.
Recommended by Sleepy Strawberry
While they handle lgbt issues differently (close knit adresses lgbt issues while in how to win at checkers nobody seems to have a problem with lgbt+) they include lgbt characters.
Both movies focus on an 11 year old kid (the child actors did an amazing job!) and both are incredibly heart breaking
Recommended by Sleepy Strawberry
both are focused on the draft day where 21 year old males participate in a lottery that determines wether they have to join the military or not. Theyre also both lgbt themed and directed by Josh Kim
Recommended by Sleepy Strawberry
How to Win at Checkers (Every Time) (2015) poster

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