Podcast Playlists

3 Addictive & Bingeable Storytelling Podcasts For Your Next Road Trip

My passion for bingeable storytelling podcasts first reared its beautiful head on the winding roads of I-95 in the winter of 2016. I was launching a bourbon company in Connecticut, and despite how fun that may sound to an outsider, it basically amounted to several months of driving by myself in a janky-ass economy rental car from one liquor store or bar to the next, repeating the same three-minute sales pitch with switched-on enthusiasm and being told to go f*ck myself a minimum of 20 times a day.

Alone and frustrated in the early-onset darkness and winter winds of the Eastern Seaboard, I desperately needed material to keep my mind off of, well…my life. Audiobooks were too slow-paced. Music allowed my mind to wander into hours of mentally telling off my insufferable cofounder. Basically, my daily sanity hinged on having something that made me excited to get back in the car and drive another 40 minutes on unfamiliar roads.

Bingeable storytelling podcasts — podcasts that spun out a single addictive story over the span of several hour-long episodes — became my life blood.  I have far too many favorites to fit in one article, but here are three of my top picks.

Up and Vanished

storytelling podcasts

Over two years later, I still lay awake at night, wishing that someday I will find another podcast as obsession-worthy as season 1 of Up and Vanished. Granted, some of my addiction and anticipation toward this podcast could be attributed to the fact that (1) as mentioned above, I had very little else going on; and (2) I was listening to Up and Vanished in real time while the investigation was actively unfolding and I was forced to wait an ENTIRE WEEK between episodes.

Since season 1 of this podcast (and the real-life investigation) have already come to a close, I strongly suggest that you refrain from doing any Googling beforehand so you can experience all of the twists and turns without having to endure six days of pining for answers between episodes like I did.

When Atlanta filmmaker Payne Lindsey decided that he wanted to explore a missing person cold case from his home state of Georgia, he decided to document his investigation on a podcast, and Up and Vanished was born. Up and Vanished was Payne’s first foray into podcasting and amateur investigating, and, fortunately for all parties involved, he turned out to be freakishly talented at both pursuits.

Season 1 of Up and Vanished covers Payne’s personal investigation into the 2005 disappearance of beauty queen and high school teacher Tara Grinsted. Disturbingly, despite having the largest case file ever compiled by the Georgia Bureau of Investigation, the case had remained unsolved for 11 years with no arrests.

As Payne began to explore old leads, he began to uncover new ones, and his podcast quickly gained national attention. The rapid movement on the Grinsted case led Payne to extend season 1 of his podcast from his originally-scheduled six episodes to a final count of 24 (not including several bonus episodes for listener questions and breaking news updates).

I want to end with the following very important disclaimer: Tara Grinsted was a real person who met an unthinkably cruel and unjustifiable demise. By highlighting my enthusiasm for the investigative journalism on Up and Vanished, I am by no means trying to make light of this case and all of its very real-life implications. Similarly, Payne did not investigate this story in the name of entertainment; his driving interest in solving this cold case was his desire for justice. He wanted the responsible parties be held accountable, and he hoped to bring some degree of closure to the victim’s family and loved ones.

P.S.: Since season 1 has aired, Payne has gone on to release a complete season 2 of Up and Vanished, focusing on the unsolved disappearance of Kristal Anne Reisinger. I recommend this season as well, but start with season 1.

Listen to Up and Vanished: iTunes || Soundcloud


S Town

storytelling podcasts

S Town is a podcast created by the producers of Serial and This American Life, so you know it’s gotta be good. This podcast is one of a kind — strange, unexpected, and deeply moving — and the story has stayed with me ever since I first heard it over two years ago.

Back in 2012, S Town’s host and executive producer Brian Reed opened an email in the general inbox for NPR’s This American Life sent by antiquarian horologist John B. McLemore. John has written to This American Life to ask if they would consider investigating an alleged murder in his hometown of Woodstock, Alabama — a place that McLemore not-so-affectionately refers to in his email as Sh*ttown (hence the name of the podcast).

Brian responds to John’s first email, and what unfolds is a fascinating and increasingly personal back-and-forth of emails and phone calls between the two men, gradually revealing many stories-within-a-story and uncovering the many sides of John’s dark, eccentric and unpredictable persona.

Eventually, Brian decides to take a trip to Woodstock. He meets the mysterious John and get a firsthand look at the complex stories that surround him.

S Town is a thought-provoking deep-dive into one person’s strange and unsettling world. Host and executive producer Brian Reed does this with a level of compassion and attention to detail that somehow manages to highlight both the depth and meaninglessness of the human experience.

Listening to this podcast wasn’t always easy. I cried, I got chills, I reflected on so many things that would otherwise pass me by. It definitely distracted me from my mindless job and put my life into perspective. If a podcast can simultaneously make you feel a little more whole and empty, this is it.

Listen to S Town: iTunes || Stitcher



storytelling podcasts

StartUp is my reigning Storytelling Podcast OG. Season 1 was released way back in 2014, when the podcasting craze was still just a twinkle in the eye of pop culture. The first season documents NPR’s Alex Blumberg on his endeavor to launch his now-wildly-successful podcast network, Gimlet Media.

Although he is currently the CEO & cofounder of (what turned into) a thriving media company, StartUp’s Season 1 Alex presents as a pretty normal radio guy with [what at the time was] a far-fetched idea. Far crazier than his idea, however, was Alex’s willingness to embark blindly — and publicly — on the road to entrepreneurship, in real time. There are many great startup-focused podcasts — such as NPR’s How I Built This, for example — that document entrepreneurial success stories in the rear view mirror. What makes StartUp different — and I would argue, far more powerful — is that it was recorded before Alex had any promise of his ultimate success.

Granted, Alex’s rolodex of Planet Money and This American Life connections may have given him an upper hand in some regard, like snagging a meeting with big-name investor Chris Sacca when he was still in the very early stages of ideation. That being said, Alex’s persona on season 1 is far from the sure-footed, destined-for-greatness visionary you might expect. In fact, even his big meeting with Chris amounts to a (sorry, Alex) cringe-worthy exchange you can hear in the first episode of season 1.

There is something wildly impactful about Alex’s decision to document the most unflattering moments of entrepreneurial depression, panic and cluelessness on the world’s stage. After all, isn’t it our ego-driven fear of failure and looking stupid that ultimately prevents so many of us from pursuing our own startup dreams? StartUp leaves the listener with no option but to accept the messy reality of launching their own business, should they choose to accept it.

Today, StartUp is in its eighth season, with each season taking on a slightly-to-dramatically-different format and focus to highlight the ins and outs of startup life. Meanwhile, Gimlet Media (the podcast network Alex set out to create in season 1) has skyrocketed to success. To date, their network produces 25 podcasts that are downloaded an estimated 12 million times per month by listeners in 190 countries worldwide. Perhaps we should see StartUp and the success of Gimlet as the ultimate proof that by putting our embarrassment and shame out in the open, we can render these forces powerless.

Listen to StartUp: iTunes || Soundcloud

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