Daily Insomnia Podcast
We're just two men with Insomnia letting our crazy thoughts spume out into the world. Join us, as we drink our way to sanity and tackle everything with a comedic touch.
Episodes
June 9, 2025 • 87 mins
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, gra...
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June 2, 2025 • 82 mins
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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May 2, 2025 • 62 mins
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 b...
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April 23, 2025 • 84 mins
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 relationsh...
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April 17, 2025 • 111 mins
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 hav...
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April 9, 2025 • 76 mins
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 curiou...
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March 27, 2025 • 97 mins
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: ...
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March 26, 2025 • 80 mins
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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March 20, 2025 • 98 mins
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 ...
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March 6, 2025 • 60 mins
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 r...
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January 17, 2025 • 94 mins
In this episode, the crew were sipping on the famous Mexican Mule with special guest, comedian and producer Melvin Stewart. The boys dive into the big egos of the Chicago comedy scene, finding love on dating apps is possible, Melvin gives inside info on the safest gamble at the casino. All this and so much more packed into another hilarious and candid conversation you don’t want to miss!
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January 8, 2025 • 66 mins
In this episode, the crew were sipping on the classic Original Mojito with special guest Jackie Linn, a talented Chicago comedian. The boys break down the worst and best moments of Demon Hour Comedy with Jackie before diving into her journey as a comedian and actress. They tackle the possibility that the guilty are actually innocent, hollywood nepotism luck or genetics gifts, and so much more. Tune in for laughs, insights, and plen...
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December 27, 2024 • 63 mins
In this episode, the crew were sipping on the famous Eastside while diving into some wild topics. The boys break down the antics of the greatest Pokémon thieve to ever live . Ramon returns with another round of his Hinge one-liners—do they hit or miss this time? Plus, they take on the ultimate challenge: how to blow through a million dollars in just one day. All this and so much more packed into another hilarious and unpredictable ...
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December 18, 2024 • 66 mins
In this episode, the crew were sipping on the classic Cuba Libre while diving into some wild topics. Is Luigi New York’s unexpected new hero or cold blooded killer? How many holes in your chones before it’s time to toss them? Plus, a hilarious discussion about dealing with smelly people and so much more. Tune in for laughs, debates, and plenty of chaos!
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October 1, 2024 • 66 mins
In this episode, the crew were sipping on refreshing Raspberry Mojitos with special guest, Chicago comedian Chris Trani. The conversation kicks off with a fun comparison between life in Spain and Mexico, and whether the USA should adopt the siesta mindset. The laughs continue as they dive into another segment of Ramon’s unhinged Hinge one-liners. Plus, the boys discuss what the Chicago Bears can do to turn things around for game 3....
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September 18, 2024 • 67 mins
In this episode, we’re sipping on the classic Highball while celebrating a big milestone—the boys have officially gone viral on TikTok! The fun continues as they break down Ramon’s Hinge one-liners, testing whether they pass or fail. Plus, we dive into the wild celebrations of Mexican Independence Day in Chicago, and so much more.
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August 26, 2024 • 102 mins
In this episode, the crew we’re enjoying the drink of the episode the bold Batanga with a special guest, Venezuelan brother comedian Christian Henningsmeyer. The guys dive into the challenges of online dating and why it often feels like a waste of time. Christian invites the boys to go speed dating with him, but are they really searching for love, or just content? The conversation heats up as everyone shares their worst date storie...
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August 16, 2024 • 56 mins
In this episode, the crew we’re sipping on the classic Cuba Libre while breaking in the new studio with some fresh vibes. The boys dive into a wild recap of a fight that broke out with the Italians at the Italian Fest on Taylor, it’s Uber or death! Tune in for all this chaos and a whole lot more as we settle into the new space and bring you the laughs!
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July 19, 2024 • 71 mins
In this episode, the crew were sipping on the vibrant Passion Fruit Sakerita while diving into some hot topics. Drinking on the job should be allowed for some people. The boys discuss why the USA might not be ready to handle a World Cup after the chaos in Miami during the Colombia vs. Argentina match. They also talk about Argentina's controversy after being recorded singing a hateful song towards France. And, in a shocking turn, Tr...
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July 11, 2024 • 59 mins
In this episode, the crew were enjoying Raspberry Mojitos. The boys discuss the importance of keeping your bad day to yourself, a surprising discovery that cheap drinks in Boys Town are no more, they also navigate a roller-coaster week for streamer Sketch, Ramon opens up about his struggles with different smells especially Gammal's. Tune in for all this and so much more!
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