Episodes

  • 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 hr and 18 mins
  • 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 mins
  • 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 hr and 32 mins
  • 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 hr and 38 mins
  • 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 hr and 5 mins
  • 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 hr and 19 mins
  • Daily Insomnia Episode 367 - The Foxtail Bandit

    Daily Insomnia Episode 367 - The Foxtail Bandit
    Aug 22 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: BUY TICKETS!
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    1 hr and 56 mins
  • Daily Insomnia Episode 366 - The eighth wonder of the world

    Daily Insomnia Episode 366 - The eighth wonder of the world
    Aug 13 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. BUY TICKETS
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    1 hr and 10 mins