Episodes

  • 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
  • Daily Insomnia Episode 360 - Battle of the Monchi's

    Daily Insomnia Episode 360 - Battle of the Monchi's
    Jun 9 2025
    In this episode, the drink of choice was the Blueberry Gin & Tonic, and the boys sat down with Chicago comedian Monchi Calvillo. They unpack the mystery behind Monchi’s name, share war stories about their history with booze, and shed light on the behind-the-scenes power plays in Chicago’s comedy world. From learning through losses to the importance of failure, it’s a real one. Demon Hour Comedy is this Friday — don’t sleep, grab your tickets now, ticket link on our IG or google Demon Hour Comedy for the eventbrite!
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    1 hr and 28 mins
  • Daily Insomnia Episode 359 - Going Forward

    Daily Insomnia Episode 359 - Going Forward
    Jun 2 2025
    In this episode, the boys kick things off with the Soju Refresher as they recap May’s electric Demon Hour show—shoutout to the crowd for bringing the heat and keeping the confessions wild. They finally made it out of the group chat and into the Cubs’ first-ever Mexican Heritage Night, and later found themselves in Wrigleyville for Bert Kreischer and Tom Segura’s Por Osos event. Comedy, culture, and chaos—it’s all here.
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    1 hr and 23 mins
  • Daily Insomnia Episode 358 - Love Letter

    Daily Insomnia Episode 358 - Love Letter
    May 2 2025
    In this episode, we’re sipping on the “Pa’ Que Marre”, a crisp and citrusy Daily Insomnia original tequila cocktail, perfect for celebrating the fact that Chicago is finally defrosting after a brutal stretch of cold. With the sun out and the patios open, the boys are feeling the shift. Ramon’s first-ever trip to a Loyola bar—and surprisingly, it was a great time. Packed with good vibes, great music, and even better company, Ramon breaks down why this bar might be one of the city’s hidden gems. The conversation takes a turn as they break down the Chicago dating scene, calling it what it is—a full-blown pandemic of ghosting, mixed signals, and low effort. They dish out their takes on what’s killing the vibe and how it might actually be fixed. All that, plenty of laughs, and so much more in this fresh spring episode!
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    1 hr and 2 mins
  • Daily Insomnia Episode 357 - Just some compas

    Daily Insomnia Episode 357 - Just some compas
    Apr 23 2025
    In this episode, we’re fueled by the smooth Run Conejo Run cocktail and joined by the homies from Compas Unfiltered Podcast for another epic North vs. South Chicago crossover. The guys chop it up about what it really takes to survive in Chicago, whether modern parents are raising soft kids, and Ramon shares a dog story that might just break your soul. From laughs to life lessons, they even break down the keys to making a relationship last—plus a whole lot more you don’t wanna miss!
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    1 hr and 25 mins
  • Daily Insomnia Episode 356 - They found me!

    Daily Insomnia Episode 356 - They found me!
    Apr 17 2025
    In this episode, we’re sipping on the smooth Whiskey Highball and teaming up with Los Kallejeros Podcast for a classic North vs. South Side Chicago clash. The boys dive into how Chicago neighborhoods have changed over time, from where Latino families first started putting down roots to how the city looks today. We also get into the city vs. suburbs lifestyle, the beauty of being a proud cholo nerd, and of course, Los Kallejeros have a little beef with the Daily Insomnia boys that needs airing out. It’s real, it’s funny, and it’s all going down in this week’s episode!
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    1 hr and 51 mins