Drew Ackerman, the creator and host of the podcast “Sleep with Me,” tells labyrinthine stories that are intended to put insomniacs to sleep—and are downloaded roughly 1.3 million times each month. Illustration by Min Heo

According to Greek myth, Hermes, the cleverest God, used his inimitable wit to tell stories so long-winded, so fatuous, that they lulled the many-eyed monster Argus to sleep. By the same logic, insomniacs of modern times are often advised to read the phone book or—the classic choice—to count sheep before bed. Unfortunately for them, there’s a good chance that such techniques are useless. Patients who counted sheep in an Oxford University study had no better luck falling asleep than a control group. Insomniacs who struggle to stay awake during presentations at work often find, when they climb into bed at night, that anxiety crowds out the body’s attempts to signal its sleepiness. In such situations, what the sleep-challenged need is not sheer boredom, a state slipped passively into, but the scantest grasp of mild amusement, from something that is distracting without being stimulating. The ideal bedtime story, according to Nitun Verma, a national spokesperson for the American Academy of Sleep Medicine, is one that “doesn’t build upon itself,” like a movie “with a lot of parallel stories that don’t connect at the end.”

Drew Ackerman, a.k.a. Dearest Scooter, the forty-two-year-old creator and host of the popular podcast “Sleep with Me,” has an ingenious intuition for this narrative balancing act. In the three one- to two-hour-long episodes he releases each week, he keeps his voice gravelly, at the bottom of his vocal range, and so slow that his upstate-New York accent takes on a tinge of Southern drawl. His sentences are mazelike constructions that turn on countless “if”s, “or”s, and “so”s; he drifts off into pointless tangents, or doubles back to ask himself if he really means exactly what he just said. His plots are equally labyrinthine: a recent few episodes centered on a magical female pirate named Lady Witchbeard; another imagined a secret war between See’s Candies and Whitman’s Samplers. In his Sunday-night-TV recaps—the most recent batch of which is titled “Game of Drones”—he might delve into a meditation on the Red Priestess Melisandre’s eldritch choker necklace, which might then inspire a detailed exploration of the science behind mood rings. Where a traditionally good yarn pulls the listener effortlessly along, the fibres of Scooter’s stories gradually unravel into wayward puffs of wool. These zany tales are downloaded roughly 1.3 million times each month; last year, the show broke iTunes’ list of top-fifty podcasts.

In one sense, “Sleep with Me” riffs on the trope of boring listeners to sleep—in his preamble, Scooter sometimes calls his show “the podcast the sheep listen to when they get tired of counting themselves.” But the brilliance of Ackerman’s technique is the way in which he calibrates his monologues to grab you ever so slightly: he seems always on the verge of being funny or interesting or profound, but, like narrative tantra, he never quite lets himself go all the way. In an episode that aired in January, he boasted of his “near ability” to tell “stories that can get to moderately interesting.” “When some people tell a story, like a Grandpa Simpson story, the needle will just barely move,” he said, whereas the “really refined” stories of a podcast like the Moth are in the “high green.” His narratives linger carefully in between, “in that old yellow zone.” “With my stories you’d say, is the oven on? It must be on. I don’t know what’s going on with your oven. It’s just, uh, it’s gonna need about twelve more hours in the oven.”

This masterfully maladroit storytelling is no simple achievement. Ackerman, who works for the library system in California’s Bay Area and started the podcast to fulfill a lifelong dream of becoming a writer, says he labors for an average of fifteen hours over every hour of “Sleep with Me,” spending much of it editing out aberrations in pacing or tone. (He recently hired his first freelance editors, and is seeking listener support or sponsorship to make the enterprise sustainable.) “It’s definitely about controlling my dynamic range,” he told me. “I’ll be like, ‘Whoa, I got a little excited there,’ so I might try to cut that out.” He studiously avoids any content that might elicit strong emotions in listeners. “Even slipping a word like ‘spiders’ in, I’ve learned, ‘Cut it out.’ ” Altogether, he has crafted hundreds of hours of stories over roughly four hundred episodes.

I first heard “Sleep with Me,” which launched in 2013, when I stayed over at the house of a friend who listens to it religiously. My own insomnia comes and goes, but I was in a bad phase at the time, and I found that I drifted off faster on her leaky air mattress, with Ackerman’s soft drone filling the dark room, than I had been able to in my bed at home. Ackerman has learned from user feedback that many of his listeners fall asleep during the twenty-minute introduction, and I’m usually one of them. I find it soothing that his openers are almost always more or less the same: Ackerman repeats some version of his pledge to “create a safe place where you can set aside whatever’s been running through your brain.” “Whatever it is that, every time you try to close your eyes or relax, it kind of jockeys for your attention,” he says, “I’m gonna take my voice here and send it across the deep dark night.” (For those who don’t like the opening, Ackerman also releases what he calls “Sleep to Strange,” a version of the podcast that goes straight into his bizarro stories.)

Listening to “Sleep with Me,” I often feel as if Ackerman’s ramblings work by tricking my brain into believing it is drifting off, emulating the peripatetic workings of the dreaming mind. But, when I asked sleep experts if that sounded plausible, they dismissed the idea. Milena Pavlova, a neurologist in the Division of Sleep and Circadian Disorders at Brigham and Women’s Hospital and Harvard Medical School, warned that, if the podcast was prolonging my slide from wakefulness to sleep—during which it’s possible to have fragmentary dreams—it might even be harming my rest. Even the doctors who saw nothing wrong with the podcast considered it, at best, “a Band-Aid,” in the words of Rafael Pelayo, a clinical professor at the Stanford Center for Sleep Sciences and Medicine. Distracting a racing mind, they insisted, was no substitute for ameliorating it through better sleep hygiene: limiting caffeine, alcohol, and screen time, and soothing anxious thoughts through meditation or circumscribed list-making before hitting the bedroom, which is reserved for “sleep and intimacy” only.

But Ackerman, who has struggled with insomnia since childhood, thinks the podcast may work, in part, because it isn’t prescriptive like a doctor’s orders—which present insomniacs with yet another opportunity for failure. The podcast “is there, but you don’t have to fall asleep,” he said. “There’s not a right or wrong way to use the show.” Though most listeners say they nod off long before the end of his tale, Ackerman is superstitious about the importance of bringing each and every one full circle, like any good bedtime story—of providing the familiar comfort of narrative wholeness. “I think, even though they never listen, the fact that the story is in some way complete is the thing that makes it work,” he said. Sometimes, he closes by simply saying thank you, individually, to a motley list of people, real and imagined. Other times, he comes up with something more fanciful. At the end of a recent episode, which consisted of an imaginary walk through a mall in the future, Ackerman sent his voice across the deep dark night to tell whoever was still awake, “Thank you. I’m just happy to know you. Thank you for spending this time walking this mall with me, it was wonderful, yes, and we will be eating our pizza together.” Yes, they still have pizza in the future. “O.K., good,” he said. “Good. Let’s get in line for the pizza. Thank you.”