He never had any awful tragedies in his childhood, but he was expelled from the University of Illinois. After that, he attended the Chicago Academy of Fine Arts.
Silverstein was married once to Susan Taylor Hastings. They had a daughter named Shoshanna Jordan Hastings on June 30, 1970. Susan died on June 29, 1975. Shoshanna died on April 24, 1982 because of a cerebral aneurysm.
I think that Shel Silverstein has these themes in his poetry because he is a little crazy and silly on his own and because when he draws the cartoons for his poems, he thinks of more deep ones.