Épisodes

  • Daily Insomnia Ep. 375 - Kat's Dilemma

    Daily Insomnia Ep. 375 - Kat's Dilemma
    Jan 15 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.
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    1 h et 5 min
  • Daily Insomnia Ep.374 - The gangs all here one last time 2025

    Daily Insomnia Ep.374 - The gangs all here one last time 2025
    Jan 6 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: BUY TICKETS!
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    1 h et 30 min
  • Daily Insomnia Ep.373 - Paper Cardinal

    Daily Insomnia Ep.373 - Paper Cardinal
    Dec 9 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.
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    1 h et 18 min
  • Daily Insomnia Episode 372 - El OG Ruben

    Daily Insomnia Episode 372 - El OG Ruben
    Nov 28 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!
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    58 min
  • Daily Insomnia Episode 371 - Companion

    Daily Insomnia Episode 371 - Companion
    Nov 11 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. BUY YOUR TICKETS!!
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    1 h et 32 min
  • Daily Insomnia Episode 370 - Who's Calling?

    Daily Insomnia Episode 370 - Who's Calling?
    Oct 27 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!
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    1 h et 38 min
  • Daily Insomnia Episode 369 - The Boyfriend Experience

    Daily Insomnia Episode 369 - The Boyfriend Experience
    Oct 2 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.
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    1 h et 5 min
  • Daily Insomnia Episode 368 - The Rabbit Hole

    Daily Insomnia Episode 368 - The Rabbit Hole
    Sep 17 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 BUY TICKETS
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    1 h et 19 min