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Light Through Things

Some things let light straight through. Some let a bit. Some let none at all.

Name
A shadow is a gap: the place light could not reach.
torcha booklight gets pastshadowlight gets pastthe wall
right throughsome gets throughnone at all
a thin curtain
tracing paper
a window
clear plastic
a wooden door
a brick wall
Which of these would make the darkest shadow?
Why does a shadow have the same shape as the thing making it?