Sean Bair-Flannery and C.J. Sullivan

Sean Bair-Flannery and C.J. Sullivan are standup comedians and friends who have been featured on Comedy Central, Sirius Radio, NPR and more. They have over 30 years of standup experience between them and about 800 missed flights. Together, Sean and CJ host The Blackout Diaries – a comedy show where standup comedians, plus ‘regular’ people (cops, firefighters, teachers, etc.), tell true drinking stories. The live show has run weekly in Chicago for over ten years and has been a critics’ pick by all major Chicago periodicals.

Every week I see a friend asking for new podcast suggestions; usually, it’s because they are about to embark on a long drive or recover from a major surgery. Have you ever noticed that podcasts are the only form of entertainment we stock up on right before our life becomes tedious?

And that’s because podcasts are the frolic of a broken society. I need to drive 75 minutes each way to my job – how do I spend almost a fifth of my waking day in traffic without wanting to kill myself? A podcast. I work a job where they tell me to undo all the work I did yesterday, to the point where I’m not even sure what skills I have anymore or if I ever had them. How do I finish eight hours of this purposelessness each day without weeping? A podcast.

America has twice (!) as many podcast listeners than all of Europe does, and that’s because we are at least twice as broken. No one starts a seven-hour car trip in Europe. They take a bullet train that gets them there before the next meal. The biggest employment sector in Europe is manufacturing – they build things! They can’t listen to a guy from Omaha do a deep dive into the oral history of Ally McBeal while running a blast furnace. Our biggest employment sectors are health and business services, which means we listen to podcasts while some a**hole from finance asks if we are “seeing the same thing” as him in Excel.

This is all completely broken. But we don’t know how to deal with that, so we listen to a person in a soft voice talk about why they think a hotel in Indianapolis is haunted.

And the majority of podcasts know they are the frolic of a broken society. They reveal themselves, not like a story or song or a fact, but a morphine drip. Slow. Repeated. Exact deploys of the same dosage; same segments at the same minutes in the same, boring voice.

We think the following podcasts work. They are not meant to be played in the background while you beg some Ford F150 towing a boat to get out of the fast lane so you can spend three more minutes with your kid today. They are meant to be laughed at uproariously or listened to conscientiously as, we feel, they are uniquely funny or interesting. In a different time or a different place where everything works, we think these podcasts would be big.


NOVA is a decades-old PBS show on natural science, which we like, not only because it answers fascinating questions but it also shows the scientific process in form and fact. NOVA discussions tend to mirror the discovery process – where we first meet a theorist who is presented as the decoder of this problem only to discover a few minutes later they were wrong about everything. Then we meet the next theorist; then we learn where they were wrong, and so on. It’s a great encapsulation of how problem-solving is tough, tiring sledding that usually slides backwards as often as forward.

It’s also (speaking of podcasts) a fascinating insight into the unhealthy zealousness of content-cliques. In NOVA, you often hear a sequence like this:

NARRATOR: “Doctor Anthony Masturzo, a professor of botany at The City College of Turin found a fossil of a leaf that, he says, proves pollen-bearing flowers developed 2 million years earlier than our current, oldest record.”

Professor Masturzo: “Finding that plant ruined my life! I’ve gotten death threats from people who believe – strictly – pollen-bearing plants developed in Yangtze river exactly 100 million years ago and not 2 years later. One guy challenged me to a duel over this!”


Frontline is, without a doubt, the best investigative journalism done on television right now and, perhaps next to a handful of print newspapers, the best journalism being done, period. Every episode is well-researched, well-told and, more importantly, focuses on a story that is vitally important to understanding our current world.

And no one below the age of sixty knows about it. For that reason, it’s equally inspiring and depressing, like the band you love that should be bigger than Imagine Dragons, off its talent, but is playing for drink tickets in Peoria.

I have seen whole episodes of John Oliver’s show where each of the substantive, revealing clips was taken from a Frontline broadcast. “People get their news off comedy shows now”, it is often said. Most troublingly, it’s said, almost as a good thing, as though we trust the comedians – modern truth-tellers, as they call themselves – more than network hacks, but what it really means is less that comedians are more truthful and more that we have become addicted to entertainment.

We can not consume facts, even facts important to our livelihood, if it’s complicated. We want to laugh. We want to be entertained. We want it distilled down to three minutes. And, as a consequence, we don’t learn that the cops in our state are allowed to pull us over for speeding and legally steal our wallet until a British comedian decides to make fun of it.

The Ladylike Podcast

Ladylike is a weekly standup comedy show in Chicago where women and people who don’t identify as men tell gross stories about themselves. It is one of the best live standup shows you can attend, with an incredible energy and highly unique aesthetic. And it’s now a podcast too!

It’s hosted by Gena Gephart, who is hilarious and unwaveringly supportive of each performer. We like this show because, besides being super funny, it’s very, very difficult to do a live standup comedy show that is focused around a single topic while still being highly relatable and consistent week-to-week.

Vanished Chicagoland Stories

Vanished Chicagoland is a podcast that was born out of the popularity of host Pete Kastanes’s facebook page of “Vanished Chicagoland” – pictures of long-since closed bars and restaurants and chains in Chicago.
We love this podcast because, like our own show The Blackout Diaries, it’s deeply Chicago. First of all, Pete probably has the least-NPR-like, podcast-like voice you will hear on an iPhone. Pete has that kind of voice where, if you have a problem with your house and you hire a craftsman to show up, and they start talking like him, you think, “oh, thank God, he def knows how to fix this.”

Our other favorite thing about this podcast is how, no matter where you are from, the places Pete talks about will remind you of your own local equivalents. Today, everything has been consolidated into five retail companies, but, growing up, we all had these weird, local businesses that are somewhere in the back of our mind – but never fetched – until Pete talks about the Chicago version of a failed amusement park or oddball ice cream parlor, and we, never knowing the Chicago version, suddenly recall our own version.

Entry Level with Brooks Wheelan

Brooks is a hilarious comedian who definitely shares our spirit for accelerant-fueled adventures. Although his podcast does not rely on that trait to produce these wildly entertaining stories. In a concept so simple and relatable, you almost can’t believe it hasn’t been done before, Brooks has a wide range of entertaining guests talk about stories from their first-ever jobs (or close to it). From Cold Stone Creamery “Super Scoopers” to giving disastrous Iowa cave tours, it’s the shared heightened stakes from our early adulthood that is forever endearing.

Ball Hog – Kevin Bozeman

Bozeman, as he is known, is a powerhouse drinker, comedian, and gambler…so naturally, he’s a favourite of ours. Just saying the name Bozeman in Chicago can alleviate you from any accountability. “What happened to you last night? // Oh man, Bozeman came through! // Say no more.“ KB’s podcast is like sitting around your favorite uncle’s chair with a glass of scotch as he chops it up about sports, culture, or whatever is on his chilled-out mind. Ball hog is a basketball term that means he’s not passing the mic, and as someone who also does a solo pod called Bottom Line Bombs on the Sports Gambling Podcast Network, C.J. knows how challenging that can be. (He couldn’t put his own pod DIRECTLY on the list, come on, we show SOME class). Maybe our favorite thing we can say about Bozeman is when we recently asked him where readers could find his show for this list, he replied, “If they truly want to find it, they will.” Like he’s challenging all of us to find the competitive spirit within ourselves to seek out and enjoy him. Coach Bozeman. 

Hunk with Mike Bridenstine

Comedian Podcasts get boorish quickly when it becomes a couple of them that are too familiar with each other just aimlessly talking about their day. Hunk is not that kind of podcast. Mike Bridenstine runs a weekly panel show with an assortment of guests that are usually meeting each other for the first time the moment the show begins to run through a rapid-fire of weekly stories and questions. It balances entertainment and pace, all while displaying effort without an agenda. Mostly the guests are comedians, like Mike Burns or Kyle Kinane (who run amazing podcasts Power Moves and No Accounting for Taste respectively) , but they also come from every facet of “real” life, which is something we try to emulate. Brido, as he is known, is the perfect anchor and captain of this spontaneous Hunk of a ship.

Valley Heat

This is a podcast about Doug Duguay’s neighborhood, the Rancho Equestrian District in Burbank, CA. It is hilarious and addicting. We swear. I mean actual hard laughter will emote, which for withered souls like us to find, is a rare gem. Doug is a freelance insurance adjuster who uses his investigating skills to try to figure out all the goings ons in the neighborhood. It’s such a fun world that we all get to participate in while peering through the curtains along with him. We almost don’t want to get too into detail in fear of relaying a bastardized version of the all too real fictional world you will enter. It’s perfect for a long road trip. Start right from the first episode and get lost in the R.E.D. Burbank neighborhood, not on your trip. Trust us.

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