Monopoly started out to show that capitalism is based on luck and opportunity, and that the end result is one person owning everything.
The whole process is miserable and even when you win you have to sit thru a prolonged ending where you slowly drain every last resource from you friends and family.
It's not a bad game, they just overestimated how well Americans can pick up irony.
Originally called "The Landlord's Game" Parker Brothers changed it to something less obviously terrible in the run up to the great depression.
I don't know if Far Side is really that deep but:
The only way to win is to not play
Is literally the point the game tries to beat over family's heads for hours at a time.