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I recognize the Plato shadows on a wall ref and someone commented about Sisyphus. Obviously, Saddam was in a hole. What's the rest? Looks like pick-axe people are part of a 2d video game. I don't get anything other than what I've described.
The pick-axe is a "motivational" meme about don't giving up, because the diamonds could be just around.
Grey downward facing body is from nutty putty cave
That story is horrifying
The caption is a reference to "The myth of sisyphus" by Albert Camus. "One must imagine Sisyphus happy". Good book.
if the books is any good is the title just clickbait?
That one is a pretty deep reference.
The gray silhouette in the hole is a nutty putty cave reference. It's pretty horrifying. Tl;dr version, cave exlorer gets so stuck it's actually impossible to remove him.