The Best, Under-Achieving, Just Okay Podcast That’s Actually Totally Useful

By Bobby Finger

Sleep With Me:

The podcast “Sleep With Me” describes itself as “a bedtime story that progressively gets more boring until you fall asleep.” With over 150 episodes available (all of which were recorded within the last year), it’s hard to choose which to listen to first. But, in my experience, they all get the job done. It’s wonderful and funny and unique and surprising, and not too long after tapping play, the sound of creator and host Drew Ackerman’s voice carries me into dreamland.

How It Works:

Ackerman begins every episode by describing how the podcast works, often with metaphors that are as bizarre as they are charming. Though not charming enough to keep you awake.

“When I’m recording the shows, I’m relaxed,” Ackerman says. “It lets me inhabit a role that I normally wouldn’t inhabit. And it puts me at ease. My success as a storyteller right now is telling stories that people don’t hear the end of. And I’m enjoying it.” The stories include serials like Dear Bezos, in which the ghosts of Richard Sears, Alvah Roebuck, and James Penney get revenge on Jeff Bezos from purgatory.

When Ackerman’s mind wanders, your mind wanders. And soon, whoops, you’re asleep.

Superdull is his long-running serial comedy about a group of bored superheroes patiently waiting for their chance to save the world. I don’t think that chance ever comes, but, again, that’s because I fell asleep.

Ackerman’s ramblings about the HBO series Game of Thrones are as effective at putting me to sleep as the HBO series Game of Thrones.

Why It’s Great:

Despite the tangents and backtracks and out-of-nowhere references to Rush Hour, “Sleep With Me” is scripted. “Writing can be draining and hopeless,” he told me. “It’s so hard to tell great stories [because of] the amount of refinement. So I thought, ‘Maybe I can do something that’s just OK. [It would] give me the security to block out that part of me that’s like, ‘No no, this isn’t good enough.’” Ackerman writes, records, and releases new episodes every 2–3 days, leaving him satisfied and his listeners drowsy.

“I don’t understand how storytelling works,” Ackerman says. “There’s something magical that happens.” If you’re lucky, the most magical part of his stories is not hearing how they end.

Follow Matter on Twitter | Like us on Facebook | Subscribe to our newsletter