Podcast Summary: Harold's Old Time Radio

Episode: Sleep No More 56-12-05 (04) Over the Hill - Man in the Black Hat
Date: September 13, 2025
Host: Harold’s Old Time Radio
Featured Reader: Nelson Olmstead
Stories by: Michael Fessier

Overview

This episode of "Sleep No More," part of Harold’s Old Time Radio, brings listeners two haunting radio stories from the golden age, both written by Michael Fessier and performed by the master of suspense, Nelson Olmstead. The first story, "Over the Hill," explores the boundary between imagination and reality as escapism turns dark. The second tale, "The Man in the Black Hat," is a surreal account of luck, chance encounters, and an enigmatic stranger who repeatedly upends the narrator’s life.

The episode delivers atmospheric storytelling, psychological tension, and a touch of existential eeriness, true to the chilling tradition of mid-century radio drama.

Key Discussion Points & Story Summaries

1. Opening Atmosphere and Set-up

(01:34-02:15)

• Host Ben Grauer introduces the show, invoking classic themes of horror: “A story of terror can be as simple as a sheeted ghost rattling chains… or it can be those terrible, fathomless shadows which lie buried deep in the primitive mind of civilized man.”

• Nelson Olmstead explains that tonight’s program features a double-bill: “Once again, Ben, we have two stories for the price of one, and this time both are by the same fine writer, Michael Fessier.” (02:15)

2. Story One: Over the Hill

Tale of Escapist Fantasy and its Unsettling Consequences
(02:15–13:59)

Summary:

• The narrator, overwhelmed by his wife’s constant nagging and crying, finds peace only by retreating into his imagination.
• He imagines driving “over the hill,” wishing everything on the other side would be different – free from responsibilities, jobs, and home life.
• One day, as he drives over the hill, his fantasy seemingly becomes real. The other side is a paradise: “It seemed like a park. The sun was shining, and there were a lot of colored flowers in the grass. And the water in the creek was blue.” (03:20)
• He meets a beautiful, kind woman and playful children in this dreamlike place. The days are idyllic and timeless.
• Suddenly, the fantasy shatters. He’s back at work, with co-workers fearful and confused by his presence.
• The boss and a policeman reveal it’s now Wednesday—not Monday, as he thought—and accuse him of his wife’s murder.
• Evidence (a bloodstain on his sleeve) confirms the crime, and the narrative blurs the line between dream, guilt, and reality.

Notable Moments & Quotes:

• “The only times I had peace was When I’d think things to myself… I like best to think about that hill.” (02:44)
• “Over the hill and on the other side. Things were as they should have been. Things were as they always should be.” (05:58)
• On confrontation with reality: "The boss's secretary came in, and with her was a policeman… The policeman pointed at the sleeve of my gray suit. 'Why shouldn't you have changed? That's why. What's that on your sleeve?'... 'It's a bloodstain.'" (13:16)

3. Story Two: The Man in the Black Hat

A Surreal, Haunting Tale of Luck and Destiny
(14:00–22:40)

Summary:

• Broke in San Francisco, the narrator discovers a sign: "This car free, inquire upstairs, room 402." His curiosity leads him to a bizarre encounter with a small, gray-eyed man in a black hat.
• The man gives away a luxury car “for no reason.” The narrator sells it, wins in the stock market, and enjoys a streak of fortune.
• The two cross paths in New York; the narrator reciprocates, offering the man a new car "for free," mirroring their first meeting.
• In Monte Carlo, the narrator loses everything at gambling until the black-hatted man appears, hands him money, and cryptically advises on how to win it back.
• The story grows more surreal as the man vanishes and reappears, eventually being arrested and executed for an inexplicable murder—yet somehow later, he meets the narrator again on a ship.
• The narrator desperately asks the man’s identity, but before an answer is given, the figure disappears: “Someday, someplace, I’m going to meet the man in the black hat again. I know he’ll tell me who he is, and I don’t want to be told.” (22:40)

Notable Moments & Quotes:

• On the mysterious giver: “They were solid gray. No iris or anything, just gray. They gave me the willies.” (15:04)
• “If I took him for granted, he was just a quiet old fellow with a gray goatee, a black hat and funny eyes. If I started figuring out how come, I’d go out of my mind.” (18:55)
• On reality’s fragility: “Surprise is that way. If I’d seen anything that was merely terrifying, I would have shrieked like a woman. But I saw the man in the black hat and I was calm. Maybe I was too stunned to be frightened or alarmed.” (20:40)
• Final existential twist: “Someday, someplace, I’m going to meet the man in the black hat again. I know he’ll tell me who he is, and I don’t want to be told.” (22:43)

Memorable Quotes & Moments with Timestamps

• "I like best to think about that hill… It would be nice, I would think, if sometime I would drive over the hill. And on the other side everything would be different." – Narrator, Over the Hill (03:00)
• "The thing was. And then it wasn't. And because it wasn't, it never had been. You can't change from something that never was to something that is." – Narrator, Over the Hill (07:28)
• “Are you the fellow that put the sign on the luxury 12 downstairs?” / "Yes… No gag at all." – Narrator and Man in Black Hat, Man in the Black Hat (15:00–15:15)
• "Have another. Give me the bottle." – The man in the black hat, (21:33)
• "Who are you? Don't you know?" – Narrator and Man in Black Hat, (22:16–22:19)
• "Someday, someplace, I’m going to meet the man in the black hat again. I know he’ll tell me who he is, and I don’t want to be told." – Narrator, (22:43)

Structure & Flow

• 00:02–01:34: Intro and station identification
• 01:34–02:15: Show and story introductions (Ben Grauer, Nelson Olmstead)
• 02:15–13:59: Story 1: Over the Hill (imaginative escape, blurred reality, dark revelation)
• 14:00–22:40: Story 2: The Man in the Black Hat (bizarre luck, supernatural encounters, existential unease)
• 22:47–24:03: Closing remarks, next episode preview

Tone & Style

The stories are suspenseful, introspective, and edged with dread. Nelson Olmstead’s narration is hauntingly calm, which heightens the psychological tension. The language is evocative, blending everyday situations with surreal, unexplained events—leaving listeners with lingering questions about reality, guilt, fate, and the unknown.

Conclusion

This episode of "Sleep No More" taps into deep human fears and fantasies—escaping a troubled life and the unpredictability of fate. Both tales, masterfully read by Nelson Olmstead, leave listeners in a state of hush and wonder, with endings unresolved and unsettling.

For fans of classic radio horror, existential mystery, and mind-bending narratives, this double feature is essential listening.