Transcribing the “ingenuously boring” world of Sleep With Me

Drew Ackerman is anything but boring, but he has a certain knack for putting people to sleep.

His popular “Sleep With Me” podcast, a series of absurdist ramblings that swirl around your brain before dropping you off in dreamland, originated out of his own lifelong struggles with insomnia.

“When I was a kid, I couldn’t sleep because I would get terrible anxiety about school. One day I discovered Dr. Demento’s radio show and it would make me laugh and put me at ease enough to be able to fall asleep.”

Drew, who narrates the show as the persona Dearest Scooter, bears more than a few resemblances to his zany radio idol, but adds a dose of mumblecore and bedtime storytelling to Dr. Demento’s schtick.

My show is for people who aren’t interested in guided meditation and who don’t want to feel guilty about falling asleep to Roman Mars,” he jokes. “People can fall asleep to me guilt-free, because they won’t miss out on anything important.”

Like improv comedy, Drew riffs off of prompts — song titles generated by iPod Shuffle, Twitter trends, Reddit topics, Venmo payments — to spin plot lines on the fly and see where they land. The trick, he says, is not being too funny or entertaining, because he doesn’t want to keep people up past their bedtime. At 420 episodes, “Sleep With Me” is a vast ecosystem of free-association sleep-inducing prolix that the New Yorker calls “ingeniously boring.”

Drew uses Pop Up Archive to transcribe episodes and create a written record of his improvised storytelling, mapping out the bizarro world he’s created. He aims to revisit certain stories and develop jokes and plot lines, just in case some listeners are actually paying attention. Plus, some people prefer to read before going to bed.







Before using Pop Up Archive, the only written record of “Sleep With Me” were these show notes written by Drew in an illegible fit of profound inspiration.

 Drew is also thinking about translating the transcripts to create foreign language spinoffs of the show, because why not?

“I got into podcasts because I love how they provide a window into other people’s worlds,” Drew says. Through “Sleep With Me,” he’s created his own fantastically mundane world — one shared with a legion of well-rested listeners.

Hear and read Sleep With Me