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!!

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.

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!

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.

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!

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!

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!

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!

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!

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!