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
August 6, 2025 • 61 mins
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...
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July 22, 2025 • 102 mins
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 wi...
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July 16, 2025 • 64 mins
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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July 4, 2025 • 99 mins
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 w...
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June 26, 2025 • 104 mins
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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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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