In honour of the newest Reply All episode “The Case of the Missing Hit, which The Guardian is hailing as the greatest podcast of all time, I’ve decided to put together a list of my favourite ever podcast episodes. Note that I’m not much of a true crime lover, and generally prefer non-fiction and/or a great story. I’ve always found it ironic that Apple named the Podcast and has no influence on it, but I’ve been listening to them since way back then. Podcasts are the best value for any form of content (free, or in some cases a subscription fee), yet even with the Western world making it a regular thing, it somehow remains underappreciated. And no, I don’t want to check out your podcast.

8. Joe Rogan Experience #1109 — Matthew Walker

To start, I hear your Joe Rogan criticisms, and frankly I think they are unfounded and dumb. Yes, he appeals to the white male more than anyone else, and sure, he may be Oprah for dudes. But Oprah doesn’t bring on scientists, researchers, and other experts to shoot the shit for 3 hours in an open forum conversation. Joe Rogan will go down as the master interviewer, and he has become extremely aware and careful of the size and influence of his platform. I’ve learned a ton from JRE over the years.

This might be my most shared podcast of all time, as it has health and wellness tips in it about the thing that everyone has the ability to improve — sleep. Matthew Walker is a PhD neuroscientist whose research focuses on the impact of sleep on health and disease. In this conversation, he gives a shockingly doom and gloom assessment on how sleep impacts quality of life, brain function, and longevity. I read Matthew Walker’s book, and vastly preferred this contained interview — he covers most of the cool insights from that in this interview. Get your 8 hours of sleep folks!

7. Reply All #102 & #103 — Long Distance (Part 1 & 2)

Yes, Reply All may have just released the best podcast of all time, but they have earned few spots on this list, and I could easily make this a Gimlet centric list. This episode of Reply All follows host Alex Goldman as he receives a phone call from a number claiming to be an Apple rep and telling him his iCloud has been compromised. We have all received calls like this, and it’s become a sign of social competence to just hang up. Alex doesn’t hang up — he begins to question where the call came from, how this is monetized, etc. His curiosity continues with him travelling to India in the second part of the episode, where he finds himself in danger, untangling a conspiracy of cold callers. A legendary, hilarious and oddly harrowing story.

6. Heavyweight #12 — Jesse

On Heavyweight, subjects confront past conflicts and demons in both story and interview format. This episode was my gateway to Heavyweight and has therefore been the one I’ve held onto. The subject in this episode, Jesse, was hit by a truck, and it inevitably changed his life. He worked his way back into reasonable condition, and he started seeking out the truck driver who hit him — to thank him. Even though the truck driver was not the one left in a wheelchair, he is in much worst condition than Jesse, and his guilt has ruined his life. This episode shows the power of forgiveness, the strength in redemption, but also the varied and surprising ways that crises impact people.

5. The Ron Burgundy Podcast — Poetry with Peter Dinklage

The general public still does not seem to have caught onto the fact that one of America’s most quotable characters has a podcast. Why does he have a podcast? After the mediocre Anchorman 2, Will Ferrell wanted a medium for the character to live on. Studio comedies have hit a weird stride, and the best parts of Anchorman are giving Ferrell a premise and letting him improvise in character. The setup here is brilliant: Ron Burgundy is down and out, no longer able to find a job on local news. He starts a podcast, but his ego, finances and celebrity have all suffered. In this particular episode, Peter Dinklage of Game of Thrones fame comes on to read from his book of poetry. Ron gets drunk, and the entire 40 minutes is occupied with the banter of Ron making fun of Dinklage’s poetry, and Peter being extremely offended. MVP of this one is Peter Dinklage for providing more than a few laughs, but this episode had me laughing out loud repeatedly, looking like a freak to strangers on the subway.

4. Tim Ferriss — Luis Van Ahn

While the 4 Hour Workweek is outdated and Tim Ferriss’ podcasts have gotten a little dry, he’s still one of our generation’s most eclectic hobbyists, public speakers and investors. This interview in particular really influenced me when I listened to it in 2015. Luis van Ahn, the CEO of Duolingo and creator of ReCAPTCHA, has been decorated as one of the world’s most brilliant scientists and minds. What is his mission? To create a platform to make language education more accessible and approachable — oh, and to give it away for free. This was one of the first times I was inspired to think that entrepreneurship doesn’t necessarily have to be capitalistic with no impact.

3. Radiolab — Juicervose

This is a podcast I commonly recommend to people who have never listened to a podcast before. A young boy is diagnosed with autism, and begins only saying one word — “juice”. Anything else I tell you after that will only ruin maybe the most satisfying and emotional moment I have ever heard in a podcast. If you don’t shed a tear or at least feel a flurry of emotion during “Juicervose”, then maybe good storytelling just isn’t for you. This is a classic Radiolab episode, using sound design as the key pillar in telling a story. The audio production for Radiolab podcasts is second to none, and because of the subject matter of this podcast, the subtleties lead to revelation.

2. Joe Rogan Experience # 877 — Jordan Peterson

Lynch me. I’m not really the biggest Jordan Peterson fan either anymore. But when it first aired in 2017 this podcast was all I would talk about with with my friends for a bout a week. We fully bought into Jordan Peterson-mania, before that mania led to hardcore right wingers taking his writings and videos out of context for nefarious purposes, and the overwhelming response from SJW’s. I’m not a defender — to Peterson’s fault, he had a very particular way of neither fanning the flame nor outright denying that people were portraying his intentions correctly. But this was before the book he wrote was accused of inspiring the Christchurch massacres, or before Peterson became addicted to painkillers and checked into rehab . At the time, before I was living dangerously being both pro-Peterson and a middle class white male, this podcast was some of the most brilliant articulation of theory, philosophy, psychology and religion I had ever seen, brought to “Joe Rogan” levels. What I mean by that is that Joe Rogan is world-class at introducing someone to a subject, or discipline at a level that does not quite dumb it down but also makes a listener feel informed. This podcast came out at the onset of Jordan Peterson’s trajectory as the modern philosopher, and while his personal videos may be more technical, this still represents a way of thinking that is unique to him.
This podcast rolls the above subjects into one and gives your average listener, intellectual or not, male or female, some modern philosophy to chew on. Enjoy.

1. Reply All #86 — Man of the People

This isn’t just my favourite podcast of all time, but possibly one of the most underappreciated human stories out there. Imagine Donald Trump, with the intellect and boldness of Tony Stark and the malicious intent of Joel Osteen in the late 1800’s around the time of the advent of the radio. That is John Brinkley, the lead character of this absolute odyssey of ridiculous. Without ruining too much, Brinkley uses this new technology in its nascency to hawk medical treatments to the largest range of people possible at the time. The stakes and antics get more and more absurd through this hour. It’s one of the greatest instances of storytelling I’ve ever experienced, and does not really on flashy production, but rather an incredible story told with humour and awe.
The podcast episode was actually greenlit into a movie starring Tony Stark himself, Robert Downey Jr as Brinkley, with Richard Linklater writing and directing.

Honourable Mentions

Joe Rogan Experience #1169 — Elon Musk

Possibly the most infamous podcast of all time, this episode was an all-timer the moment Elon Musk stepped into Joe Rogan’s studio and for 2 hours before the fateful joint puff moment. Joe Rogan is no stranger to having CEO’s, intellectuals and scientists on his podcast, but the answers he gets from Elon Musk in this interview after he gets comfortable are profound and informative. The whole interview is very surreal.

Radiolab — Punchline

A Radiolab episode about sports? Neat! This episode covers the absurd campaign to vote journeyman NHLer John Scott, a career goon, into the 2016 NHL All Star. The viral campaign turns into a story of corruption and ultimately becomes an inspiring tale with a sports movie moment for the ages

Caliphate — Chapter Five: The Heart

New York Times’ “Caliphate” is an exercise in perspective, and Chapter Five for me was the episode where the viewer is forced to question all information they have been given. Rukmini Callimachi tells the story of a young man who is recruited from his comfortable life in the US to join the Islamic State in Syria. He returns on his own volition, but is anything but reliable in his testimony. Callimachi uses “the recruit’s” story to answer questions about the Islamic State, but the boy’s story is by far the most captivating part of this podcast. It is touching, scary, and oftentimes relatable.

I’m a young professional living in Toronto, running a creative artificial intelligence startup.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store