My Theory About Shep
I've been a longtime Jean Shepherd fan. I have a theory about Shep, and I have no one else to share it with besides the readers of this sub.
I read the Jean Shepherd biography Excelsior You Fathead. There is an incident described where Jean fell from a great height off a telephone pole during army training. He was hospitalized for quite a while. Also, I found in an index of Jean Shepherd radio programs a broadcast with the subject "Trying Psychedelics" (or something like that) from 1963.
If you want to know where Shep got his philosophical insights that no one else had, I suspect that he had a near-death experience during his army accident; and that he tried LSD sometime in the early '60s and had the kind of "transcendent" experience that people who have used psychedelics often report.
People who have had near-death experiences have a different outlook on life and enhanced views on spiritual matters. They no longer fear death. You combine that with cosmic insights gained using psychedelics (even once), and these two things would explain how our beloved Jean Shepherd was able to describe and discuss deep philosophical truths (often using parables) in ways that were easy for his audience to understand (and have fun doing it!)
This is not to take away from Shep's natural talent. I am merely theorizing that these two experiences acted as an "enhancer", and would help explain why Jean Shepherd's insights and approaches were so unique.
What do you think?