My generation knows Jean Shepherd as the source material and chortling narrator for A Christmas Story (wp). But Donald Fagen remembers "Shep" as a distinctively subversive personality:
"From Bert the Turtle's exhortations to 'duck and cover' in the face of an atomic blast to the endless parade of new products hawked on the tube by Madison Avenue, Americans were feeding themselves a line of hooey that was no less absurd than the most hard-core Maoist brainwash. 'Relax, life is good,' we were told. 'Your government and Walt Disney have got the future well in hand.' To skeptical Mad magazine-reading little stinkers like myself, it was this mendacity on the part of adults that was the most sinister enemy of all. Because Shep made it clear he was just as dazed, enraged, and amused as you were, that he noticed what you noticed, he established himself as one of a handful of adults you could trust."
If that seems a little rich, don't just read the piece: hit the sound-files too. Fagen brushes away a little of the "protective coloration" and reveals some of the man's discomfiting depth of character, here.