Episodes

  • 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
  • Daily Insomnia Episode 365 - The voice of Demon Hour

    Daily Insomnia Episode 365 - The voice of Demon Hour
    Aug 6 2025
    In this episode, the boys sip on classic Mojitos with special guest Kevin Kellam—the voice of Demon Hour Comedy himself! They look back on some wild Demon Hour moments and how the show has leveled up over the last year. Kevin gets his flowers for being a killer host, mentor, and all-around showman. The crew dives into Kevin’s upcoming comedy album recording on August 9th at Lincoln Hall, and the fire that pushed him to finally make it happen. Plus, what does the perfect pre-show day look like for Kev? Oh—and Ramon reads Gammal’s eulogy. Yeah, you read that right. Real laughs, real love, and so much more.
    Buy tickets to Kevin's Kevin and Hell album tape for this Saturday August 9th 9pm at Lincoln Hall!! TICKET: lh-st.com/shows/08-09-2025-windy-city-comedy-festival-late
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    1 hr and 2 mins
  • Daily Insomnia Episode 364 - From Milwaukee with love

    Daily Insomnia Episode 364 - From Milwaukee with love
    Jul 22 2025
    Drink of the episode was the Margarita, and joining the boys was the hilarious and beautiful Maria Acosta—a Milwaukee native now holding it down in Chicago. Maria calls out the lack of hugs, gives us the lowdown on Milwaukee’s comedy scene and its deep-rooted segregation, and dishes on dating in Chicago. Are girls meaner here? Is the comedy scene full of mean girls? The crew gets into all that and more in this funny, honest, and wide-ranging episode.
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    1 hr and 43 mins
  • Daily Insomnia Episode 363 - Unicorns are real

    Daily Insomnia Episode 363 - Unicorns are real
    Jul 17 2025
    This week, the boys cool off with Mexican Mules and gear up for a wild 4th of July. Ramon breaks down his party dominance, Gammal questions vacation stamina, and they both agree—they're officially Chicagoans now. From unicorns at the Riverwalk to full-blown holiday strategies, this episode brings the laughs and then some.
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    1 hr and 5 mins
  • Daily Insomnia Episode 362 - Get me in coach

    Daily Insomnia Episode 362 - Get me in coach
    Jul 4 2025
    In this episode, the drink of choice is the classic Cuba Libre, and the boys welcome back a very special guest — Chicago Latino comedian Oscar Carbajal, the OG who helped launch the Daily Insomnia Podcast into the local comedy scene. They give Oscar his well-deserved flowers, catch up on his comedy journey, and reminisce on some early episodes. From updates on the Chicago grind to deep dives into soccer, the Gold Cup, and whether we'll ever see Mexico in a World Cup final — it's a full-circle episode you don’t want to miss. DEMON HOUR NEXT WEEK FRIDAY, TICKET LINK IN OUR IG & TIKTOK!!
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    1 hr and 39 mins
  • Daily Insomnia Episode 361 - A couple of metro's

    Daily Insomnia Episode 361 - A couple of metro's
    Jun 27 2025
    In this episode, the crew sips on east sides with special guest comedian Ashley Lusk. They dive into why she loves Demon Hour Comedy, the chaos of dating within the comedy scene, The groups wild take on Pocahontas tripping on shrooms. Some deep stories from her upbringing. Honest laughs, weird moments, and plenty more packed into this one.
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    1 hr and 45 mins