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We're just two men with Insomnia letting our crazy thoughts spume out into the world. Join us, as we drink our way to sanity and tackle everything with a comedic...
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We're just two men with Insomnia letting our crazy thoughts spume out into the world. Join us, as we drink our way to sanity and tackle everything with a comedic touch.
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Episodes & Posts
Episodes
Posts
Transcribed
15 JAN 2026 · In this ep the drink of the podcast was rum & coke, and we kick off the year the right way—with award-winning comedian Kat Diaz in the room. We jump into the Chicago comedy scene and the whole awards conversation—what it means, what it doesn’t, and why we might end up creating our own just to stir the pot. Then it turns into real shop talk: what actually makes a comedy show work and all the little details that separate a solid night from a great one. We debate the question every producer argues about: is 7:00 PM a perfect time slot, or is it too early for people to really be ready to laugh? Kat takes it left with her “perfect man is blind?!” theory, and then we get into a real moment—four years sober? It’s funny, honest, and a strong start to the year… and we definitely go plenty of other places too.
Transcribed
6 JAN 2026 · Ramon, Gammal, and Rambo close the year together, grateful for finding each other in 2025 and for how that chemistry kept breathing life into the show. They talk about chasing a fresh start—and how even good surprises can reroute the plan. Rambo takes us inside Skankfest with a full breakdown of his adventure: the rooms, the comics, the lessons. Then the boys unpack the headline story—Logan Paul and Andrew Tate both taking losses—how it happened, what it says about hype vs. substance. They wrap with a heartfelt thank you to everyone who supported Daily Insomnia Podcast and Demon Hour Comedy this year for 2025 also special appearance... and so much more.
Demon Hour Comedy this Friday: https://www.eventbrite.com/e/demon-hour-comedy-chicagos-raw-and-untamed-confessions-tickets-778031311597?gclsrc=aw.ds&&utm_source=google&utm_medium=ebps&utm_campaign=PSNB_CUAL_PMK_PDO_MEC_US_CHI_BAU_0_GA01-CATEGORIES-AI-Max&utm_term=comedy%20events%20chicago&aff=ebmkmxperformance&gad_source=1&gad_campaignid=23050334324&gbraid=0AAAAAo0IdU2Cf7RtYAk04hRZoP0xnVTwu&gclid=EAIaIQobChMI0I_h3Lb3kQMVdjUIBR04eAUyEAAYASAAEgLhsPD_BwE
Transcribed
9 DEC 2025 · In this ep the drink of the podcast was the Monkey Jam Sour—bright, tart, and perfect for story time. We’re joined by Paper Cardinal, a local Chicago band, for a high-energy walk down memory lane. The guys trace how the group formed, how sessions at Fort Knox (Chicago) sparked their newly released album Jupiter Run, and what really separates an EP from a full album—creatively, strategically, and for fans. Big theme of the night: you can’t just stack ideas; you’ve got to move on them. We cap it off with the hype: this Wednesday is Paper Cardinal’s first headlining show as a full group at the Cobra Lounge Chicago—and there’s plenty more where that came from. Grab a drink and enjoy this episode with us.
Transcribed
28 NOV 2025 · In this episode, the drink of the night was the Gin Mule, and the boys were joined by special guest Ruben Ramirez — comedian, content creator, and the OG host of Demon Hour Comedy. They dive into how content creation is finally getting the respect it deserves, and how Ruben’s nonstop hustle sets the example for up-and-coming comedians in the scene. The crew reflects on Demon Hour Comedy’s growth over the past year, drops 30 minutes of Spanish content for the fans, and keeps the laughs rolling with plenty more stories and insights along the way!
Transcribed
11 NOV 2025 · In this episode, the drink of choice was the classic Mojito, and the boys admit to having a pretty boring Halloween — no costumes, no parties, just vibes. They take a nostalgic trip down video game memory lane, reminiscing about the good old days of Fortnite before it got sweaty. The guys also react to the latest in tech — a new AI robot that can wash your dishes (finally!). Plus, a fresh round of wild listener calls in this week’s “We’re Listening, Chicago” segment, and so much more!
This Friday, 9pm Demon Hour Comedy at the Lincoln Lodge Chicago. https://www.eventbrite.com/e/demon-hour-comedy-chicagos-raw-and-untamed-confessions-tickets-778031311597?aff=oddtdtcreator
Transcribed
27 OCT 2025 · In this episode, the drink of choice was Tequila High Noons, and the boys get right into it — nothing breaks their hearts more than a married woman bad-mouthing her husband to strangers. What started as “one more drink” on a Sunday night spiraled into a trip to see midnight ballerinas in action, where the boys discovered that maybe, just maybe, the dancers could use a refresher course on how to treat their patrons better. The guys also debut a brand-new segment, “We’re Listening, Chicago,” where listeners call in and answer the boys’ wild questions. All that and plenty more laughs, drinks, and chaos in this one!
If you'll like to be a caller, follow us on instagram or tiktok Daily Insomnia Podcast for our questions and call 312.967.2551 to leave your voicemail answer to our questions. Thanks yall!
Transcribed
2 OCT 2025 · In this episode, the cocktail of the night was the classic Mojito, and the boys were joined by their Venezuelan brother and Chicago comic Christian Henningsmeyer. As always, the Daily Insomnia crew hypes up their guy before diving into the wild world of the Chicago dating scene. From women’s endless lists of icks, to how both sides view what makes a date “bad,” to the truth that some women have no game, nothing is off limits. The conversation gets even spicier with talk of escort pricing in Chicago, the boys’ own kinks and search histories, and plenty more chaos along the way.
Transcribed
17 SEP 2025 · In this episode, the boys talk about how the Taco Bell dog got canceled and why 90’s fast food was made with love. They get into how big chains lose their quality after buyouts, call Au Cheval overrated, and crown Kuma’s as Chicago’s true burger king. From the “token family member” everyone seems to have, to strip club culture, and even a rabbit hole on the women of the night, this one’s got laughs, hot takes, and plenty of chaos. Demon Hour Comedy this Friday https://www.eventbrite.com/e/demon-hour-comedy-chicagos-raw-and-untamed-confessions-tickets-778031311597?aff=oddtdtcreator
Transcribed
22 AUG 2025 · In this episode, the drink of the night is the refreshing El Niño — a bold mix of mezcal, cucumber, and serrano pepper. Special guest Phil Lisiecki (producer of Wild Philosophy and Wild Dogs Comedy) joins the boys as they dive into his comedy career and the lessons he’s learned along the way. From why being personable is the best way to network, to Phil and Shapel Lacey bonding over Oasis (while Rambo and Phil hilariously explain who Oasis even is), to the nightmare of workplace hazing — this episode packs laughs, stories, and plenty more.
Demon hour Comedy this August 22nd 9:30pm: https://bit.ly/demonhour19
Transcribed
13 AUG 2025 · Rum Mule in hand, laughs on deck. We sat down with one of our favorite comics, Mike Dwyer, to break down July’s packed Demon Hour and his hilarious, one-of-a-kind style. Mike gets real about the moments that shaped him, drops some comedy wisdom, and keeps us cracking up the whole way. This one’s got stories, laughs, and a little heart. Don't forget Demon Hour Comedy next week Friday August 22nd. https://bit.ly/demonhour19
We're just two men with Insomnia letting our crazy thoughts spume out into the world. Join us, as we drink our way to sanity and tackle everything with a comedic...
show more
We're just two men with Insomnia letting our crazy thoughts spume out into the world. Join us, as we drink our way to sanity and tackle everything with a comedic touch.
show less
Information
| Author | Daily Insomnia |
| Organization | Daily Insomnia |
| Categories | Comedy |
| Website | - |
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