Episodes

  • 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
  • Daily Insomnia Episode 355 - Wrestling the Aliens

    Daily Insomnia Episode 355 - Wrestling the Aliens
    Apr 9 2025
    In this episode, we’re sipping on the bold Batanga and taking another trip down memory lane—yes, we’re talking about our high school wrestling careers… again. The boys get deep, reflecting on the beautiful souls walking this earth, dive into the mystery of the pyramids and what’s been discovered underneath them, and shed some light on the Phoebus cartel and the sketchy history of lightbulbs. All that and so much more in this curious, chaotic, and classic episode!
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    1 hr and 17 mins
  • Daily Insomnia Episode 354 - Luck of the Mexican

    Daily Insomnia Episode 354 - Luck of the Mexican
    Mar 27 2025
    In this episode, the boys are cooling off with the refreshing East Side cocktail while soaking in all the good vibes. They talk about how drinks and food just hit different outside, why limes are the MVP of both cocktails and bar life, and how some folks still haven’t figured out basic comedy show etiquette. They also recap their wild St. Patrick’s Day in River North, and stumble upon the ultimate “bog song”—sparking the question: how white can we go? All that and so much more in this fun, chaotic, and unfiltered episode!
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    1 hr and 38 mins
  • Daily Insomnia Episode 352 - Little Foot Big Foot

    Daily Insomnia Episode 352 - Little Foot Big Foot
    Mar 26 2025
    In this episode, the crew were sipping on Mezcal Mules. The boys take on the "Casanova" Sling Blade, unraveling how Halle Berry was once linked to Billy Bob Thornton, we break down our favorite Batmans, and we revisit the legendary moment when Tom Segura blew out his elbow and knee trying to dunk. Plus, we go through some of the best confessions from our last Demon Hour and so much more!
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    1 hr and 21 mins
  • Daily Insomnia Episode 353 - Dj Wisdom

    Daily Insomnia Episode 353 - Dj Wisdom
    Mar 20 2025
    In this episode, the boys welcome special guest Cesar Popoca, a local Chicago EDM DJ, while sipping on the smooth Whiskey Smash. They take a trip down memory lane, reminiscing about the greatest party McHenry County ever saw in 2015. Cesar gives us a behind-the-scenes look at the wild nightlife of a club DJ, from crazy crowds to late-night chaos. Plus, the boys play it cool after spotting a famous comedian at the bar. All this and so much more in another episode packed with stories, laughs, and late-night vibes!
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    1 hr and 38 mins
  • Daily Insomnia Episode 351 - Do Better

    Daily Insomnia Episode 351 - Do Better
    Mar 6 2025
    In this episode, the crew were sipping on Gammal’s tequila concoction while diving deep into some big changes. The boys have been doing some soul-searching and have officially brought in a new producer for the podcast! They also take a moment to reflect on the recent passing of a great Chicago comedian and break down exactly how NOT to run a comedy club. All this and so much more—tune in for laughs, insights, and some much-needed real talk!
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    1 hr and 1 min