Like a lot of fine-tuned performing artists, Shepherd increasingly exhibited the whole range of symptoms common to the aging diva. He became paranoid and resentful of imagined rivals, whether they were old ones like Mort Sahl or upstarts like Garrison Keillor. At the same time, he disavowed all his radio work, claiming that it was just a temporary gig on his way to some fanciful glory on the stage and screen. He even seemed to want to kill off his childhood, insisting that all those stories and characters were pulled clean out of his imagination. Old fans, for whom he had been almost like a surrogate father or big brother, were often met with derision when they approached him.
He didn't drink himself to death like his pal Jack Kerouac or OD like Lenny Bruce but gradually succumbed to that very real disease of self-loathing and its accompanying defenses. Disappointed in the way the world had treated him, he retired to Florida's west coast and died in 1999.
Although Shepherd almost never divulged details about his private life, he wasn't shy about giving us a bit of unflattering self-analysis, as this fragment of a show from 1957 attests:
Protective coloration is extremely important in our lives. ... [W]e are in the weeds all the time because we find it better down here in the weeds. ...
Look at me. ... I am not at all what I appear to be. ... [T]his is merely a mask ... that more or less covers up the real me that's underneath. The real me is a saber-toothed tiger. I couldn't dare go down the street the way I really am. I'd get shot in five minutes. They'd have me in a wagon with a bunch of Doberman pinschers.
To an adolescent back then, long before a therapeutic vernacular had entered the language, this was reassuring news. It's possible that Shep's greatest lesson to the gang wasn't just "things are not what they seem" but rather "things are not what they seem—including me."