Jean Shepherd has been a prominent obsession of mine for a long time. Both my parents grew up listening to him on WOR radio in New York, where he did a 45-minute show every weeknight for over 20 years.

What did he do for 45 minutes? Tell stories about his youth in a northern Indiana steel town, or his years in the Army during World War II, and ruminate on the human condition, virtually uninterrupted. He would weave tales, veer off on tangents, and catch you up in his verbal wave. And then, just as the end credit music swelled and you thought he could not sew everything up in time, he did.

The fact that he did this five days a week (plus several years of a simulcast, two-hour live weekend gig at a Greenwich Village club called The Limelight), completely off the top of the dome, is nothing short of mind blowing. If he’d done his work in virtually any other medium, he would have won 10 Pulitzers. Unfortunately, he worked on the radio, a medium that’s as disrespected as it is ephemeral.

His show was resolutely anti-commercial. He was certainly not averse to making a buck, but he had little interest in changing anything about himself or making nice in order to do it. He would often mock the ads that ran during his show, or talk over them, or if he was reading the copy himself, punctuate it with his own observations that weren’t germane (or flattering) to the product being discussed.

He also constantly tweaked WOR, a button-down conservative station where he stuck out like a sore thumb. During station IDs, he would often tie in a topic or prhase he just mentioned. (“Speaking of the trivial, this is WOR AM and FM, New York…”)

It was, in other words, the kind of show you simply can’t do on radio anymore. The closest thing to it, vaguely, is The Best Show on WFMU, because WFMU doesn’t have to deal with commercials, so the show can proceed at its own pace. But a major part of The Best Show is its guests and callers–particularly the long calls between Tom Scharpling and characters played by Jon Wurster. Shep, on the other hand, never spoke with anyone but himself. He delivered his monologues as if having a conversation with you, the listener, but really he just needed a microphone to write novels out of the air.

This time of year makes me think of Shep because nowadays, if he’s remembered at all, it’s as the writer of A Christmas Story, the holiday favorite that’s inescapable every December. Shepherd also narrated the movie; that’s his devilish, mellifluous voice you hear throughout the film, punctuating it with priceless lines like “the soft glow of electric sex”.

I like A Christmas Story a lot, but as great as it is, it does not have the same tone or feel as his radio shows. It’s much more sweet and nostalgic. In fact, Shepherd initially dismissed the movie once it bombed at the box office. (To give you an idea of the angle he wanted, his screenplay was initially titled Santa’s Revenge.) He only embraced A Christmas Story later when it made him a millionaire.

In his tales of kid-dom, the themes he always came back to were pain, disappointment, and disillusionment. This has always resonated with me, because I feel that most adults idealize childhood to a ridiculous degree, when in fact childhood is often terrifying. Early in his radio heyday, Shep told an interviewer, “Childhood seems good in retrospect
because we were not yet aware of the basic truth: that we’re all losers,
that we’re destined to die and death is a defeat.”

The kids in his stories don’t have happy endings. They don’t get what they want, and if they do, it becomes a Pyrrhic victory. He begs and begs for a BB gun, only to be thwarted at every turn (even by Santa himself), and when he finally gets the object of his desire, he nearly shoots his eye out. He scrimps and saves to get a Little Orphan Annie secret decoder ring, then discovers to his horror that it’s just a marketing tool. (A crummy commercial?)

I discovered Shep for myself thanks to the interwebs in the late 1990s, when old fans of his who taped his shows back in the day began to digitize them for the rest of the world to hear. To be sure, not everything holds up, and Shep occasionally busts out an embarrassing ethnic accent (think Krusty the Clown’s “me so sorry!” act). But far,
far more of his shows are relevant than not. It’s truly remarkable.

For years, I would corner any acquaintance of mine and insist they had to listen to his old shows. Because I’m an evangelist by nature, and also insane. Few heeded my pleas, and I don’t blame them, because when you think of Old Radio, you think of creaky stuff like Fibber McGee and Molly and other shows that have not aged well. Plus, there is a lot of Shep out there. It’s hard to know where to begin.

In my own opinion, you can’t go wrong with any Shep show from the 1960s. Earlier in the decade, his shows were much more somber and dark. Over time, he gradually crafted himself into a master storyteller; 1963-1969 or so is his high watermark. By the time the 1970s rolled around, his show was saddled with more commercials, and he saddled himself with more extracurricular activities (a PBS series, short stories for Playboy). The shows suffered for it, and by 1977, his lack of commercial appeal caught up with him. He either resigned or was fired from WOR, depending on who you ask, and sadly spent the rest of his life completely dismissing his brilliant radio work, bitter over what happened to the medium.

Here I present a few of Shepherd’s holiday/winter tales for your perusal, so you can judge for yourself. The first is the saga of his friend Flick sticking his tongue to a flagpole on a cold winter morning–later immortalized in A Christmas Story, heard here in a show from 1968.

As back story, the “Dayak curse” Shep refers to at the beginning of this show was a prank/experiment he did several times on his show (one of his few “recurring gags,” if you will). He would play a recording of some spooky-sounding, Eastern music and say that it was a special flute crafted in the wild jungles of Borneo as an instrument of war, designed to kill anyone under a certain age. Since his audience skewed pretty young, it was a frightening prospect to the vast majority of them.

Download file here.

In this second show from 1963, Shep talks about buying a gift for his mother that he thinks is really gonna knock her socks off: a perfume atomizer. Plus, a glimpse into the bygone days of ordering Christmas gifts by radio.

Download file here.

Finally, this last program from 1964 isn’t a Christmas-related show, but it is seasonal, and a perfect example of Shep’s story-telling powers. In it, he recounts The Great Indiana Blizzard that tore through his town one winter.

Download file here.

If you dig any of this, I suggest checking out FlickLives.com, which has tons of info on Shep and lots of shows for download. There’s also a podcast, The Brass Figlagee, which has literally hundreds of Shep shows for download.

He’s one of the greatest artists of the 20th century you’ve probably never heard of, and we’ll never see another like him again. I hope you enjoy the selections above.