I love pretty much all Comics, TV, Movies, Books, and Video Games. I love it more when the awesome people of the internet combine them into other awesome stuff. Let your imagination run wild.
Death doesn’t cry, of course not. He is a skeleton, lacking glands, and hormones. Oh, and flesh and bodily fluids. He doesn’t have that either.
So Death does not cry.
But there are times when the lights in his eyes go out for awhile.