Episodes
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Daily Insomnia Episode 381 - Chicago Summer Nights
In this episode, the boys are back after a 3-month break and waste no time jumping into one of the best nights of the summer—RÜFÜS DU SOL at Wrigley Field. With perfect 70-degree weather... it felt like a dream. The boys talk about why nothing beats a Chicago summer night and how the city comes...
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Daily Insomnia Episode 380 - The Voice of Demon Hour
In this episode, the drink of the episode was mimosas and the boys are in the studio with special guest, Chicago comedian Kevin Kellam. They go down memory lane, reflecting like they’re right back in late August sitting in the crowd watching Kevin perform and film his first special Kevin in Hell…
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Daily Insomnia Episode 379 - Chicago Shenanigan
In this episode, the boys are back after a wild two-week stretch — from the chaos of St. Patty’s Day to a Latino rock night at Navy Pier’s Bar Sol. They get into how Cesar Chavez is being erased from history at an alarming rate, and dive into a deeper convo: can evil people have good intentions…
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Daily Insomnia Episode 378 - Charming Ritual
In this ep the drink of the podcast was Run Conejo Run, and we bring in our first band of the year—Charming Ritual—for a special episode. We jump straight into the band’s story: how Charming Ritual started, how it’s going, and the moments that shaped them—from early Chicago venue gigs to sweaty...
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Daily Insomnia Episode 377 - Los Tios
In this ep the drink of the podcast was the Cuba Libre, and the duo is back to close out February with a classic Insomnia-style spiral. We jump from culture to chaos real quick—talking about “delicacies” from different cultures and how some foods sound wild until you realize every culture has...
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Daily Insomnia Ep.376 - Start of the year
In this ep the boys go full Insomnia rabbit hole and refuse to tap out. We admit we’ve been slacking, but we’re not leaving—and Ramon’s in that “cocoon” phase, talking like he’s transforming into something big for this Sunday. From there it’s rapid-fire chaos with purpose: the wins and losses of...
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Daily Insomnia Ep.375 - Kat's Dilemma
In this ep the drink of the podcast was rum & coke, and we kick off the year the right way—with award-winning comedian Kat Diaz in the room. We jump into the Chicago comedy scene and the whole awards conversation—what it means, what it doesn’t, and why we might end up creating our own just to…
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Daily Insomnia Ep.374 - The gangs all here one last time 2025
Ramon, Gammal, and Rambo close the year together, grateful for finding each other in 2025 and for how that chemistry kept breathing life into the show. They talk about chasing a fresh start—and how even good surprises can reroute the plan. Rambo takes us inside Skankfest with a full breakdown of...
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Daily Insomnia Ep.373 - Paper Cardinal
In this ep the drink of the podcast was the Monkey Jam Sour—bright, tart, and perfect for story time. We’re joined by Paper Cardinal, a local Chicago band, for a high-energy walk down memory lane. The guys trace how the group formed, how sessions at Fort Knox (Chicago) sparked their newly…
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Daily Insomnia Episode 372 - El OG Ruben
In this episode, the drink of the night was the Gin Mule, and the boys were joined by special guest Ruben Ramirez — comedian, content creator, and the OG host of Demon Hour Comedy. They dive into how content creation is finally getting the respect it deserves, and how Ruben’s nonstop hustle sets...
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Daily Insomnia Episode 371 - Companion
In this episode, the drink of choice was the classic Mojito, and the boys admit to having a pretty boring Halloween — no costumes, no parties, just vibes. They take a nostalgic trip down video game memory lane, reminiscing about the good old days of Fortnite before it got sweaty. The guys also...
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Daily Insomnia Episode 370 - Who's Calling?
In this episode, the drink of choice was Tequila High Noons, and the boys get right into it — nothing breaks their hearts more than a married woman bad-mouthing her husband to strangers. What started as “one more drink” on a Sunday night spiraled into a trip to see midnight ballerinas in action,...
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Daily Insomnia Episode 369 - The Boyfriend Experience
In this episode, the cocktail of the night was the classic Mojito, and the boys were joined by their Venezuelan brother and Chicago comic Christian Henningsmeyer. As always, the Daily Insomnia crew hypes up their guy before diving into the wild world of the Chicago dating scene. From women’s...
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Daily Insomnia Episode 368 - The Rabbit Hole
In this episode, the boys talk about how the Taco Bell dog got canceled and why 90’s fast food was made with love. They get into how big chains lose their quality after buyouts, call Au Cheval overrated, and crown Kuma’s as Chicago’s true burger king. From the “token family member” everyone seems...
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Daily Insomnia Episode 367 - The Foxtail Bandit
In this episode, the drink of the night is the refreshing El Niño — a bold mix of mezcal, cucumber, and serrano pepper. Special guest Phil Lisiecki (producer of Wild Philosophy and Wild Dogs Comedy) joins the boys as they dive into his comedy career and the lessons he’s learned along the way.…
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Daily Insomnia Episode 366 - The eighth wonder of the world
Rum Mule in hand, laughs on deck. We sat down with one of our favorite comics, Mike Dwyer, to break down July’s packed Demon Hour and his hilarious, one-of-a-kind style. Mike gets real about the moments that shaped him, drops some comedy wisdom, and keeps us cracking up the whole way. This one’s...
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Daily Insomnia Episode 365 - The voice of Demon Hour
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…
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Daily Insomnia Episode 364 - From Milwaukee with love
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...
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Daily Insomnia Episode 363 - Unicorns are real
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...
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Daily Insomnia Episode 362 - Get me in coach
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…
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Daily Insomnia Episode 361 - A couple of metro's
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...
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Daily Insomnia Episode 360 - Battle of the Monchi's
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...
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Daily Insomnia Episode 359 - Going Forward
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...
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Daily Insomnia Episode 358 - Love Letter
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...
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Daily Insomnia Episode 357 - Just some compas
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...
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Daily Insomnia Episode 356 - They found me!
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…
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Daily Insomnia Episode 355 - Wrestling the Aliens
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...
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Daily Insomnia Episode 354 - Luck of the Mexican
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…
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Daily Insomnia Episode 352 - Little Foot Big Foot
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…
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Daily Insomnia Episode 353 - Dj Wisdom
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…
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Daily Insomnia Episode 351 - Do Better
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...
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Daily Insomnia Episode 350 - Big Boy
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…
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Daily Insomnia Episode 349 - What Is A DP?
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...
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Daily Insomnia Episode 348 - Den of Thieves
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...
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Daily Insomnia Episode 347 - Day 1
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…
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Daily Insomnia Episode 346 - Our Favorite Trani
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...
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Daily Insomnia Episode 345 - Pickup Artist
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…
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Daily Insomnia Episode 344 - Love or Content
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…
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Daily Insomnia Episode 343 - City Boy's
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…
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Daily Insomnia Episode 342 - We All Need A Break
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...
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Daily Insomnia Episode 341 - Skeletons In The Closet
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...
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Daily Insomnia Episode 340 - Merica
In this episode, the crew were sipping on the bold Batanga Mezcal while diving into the only ways to celebrate the 4th of July. The guys chat about "White Girl Summer" the rise of TikTok white girls. They also delve into some classic podcast lore "the joke that nevers end" and share plenty more…
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Daily Insomnia Episode 339 - Ruben Ramirez
Hey guys, in this episode featuring comedian Ruben Ramirez from Chicago, the atmosphere was pure chaos, he joined to promote his upcoming comedy show in Milwaukee. The conversation was filled with jokes and banter among the crew, touching on topics such as dating, fitness, comedy scene in…
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Daily Insomnia Episode 338 - Wounded Animal
In this episode, the crew enjoyed the bold Batanga cocktail. Ramon ego gets crush by a couple of torta's, breaking legs for an inch of difference worst decision you can make, favoritism rules for step-dads and is drinking at work underrated. Tune in for all this and so much more!
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Daily Insomnia Episode 337 - Rest In Peace
In this episode, the boys are sipping on the refreshing Raspberry Mojitos while diving into an eventful weekend. Gammal shares his story of a huge loss, but don't worry—he quickly bounces back as the boys embark on an adventure in Milwaukee. We also discuss the historic news of Mexico electing…
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Daily Insomnia Episode 336 - Where's The Talent
In this episode, the crew kicked things off with the crisp and refreshing Green Apple Delight. The guys dive into a discussion about Kardashian nepotism rearing its head in the Lion King casting. They also unpack the wild scenes from this weekend’s Sueños Fest—did things go too far? Plus, Ramon's...
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Daily Insomnia Episode 335 - Stay Alert
This episode, the crew were sipping on Blackberry Mexican Mules and diving into some intense topics. First up, talking about staying sharp and ready for anything life throws at them, dad who gave a beatdown to his daughter's bully father, slow and steady is sometimes the best approach, old...
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Daily Insomnia Episode 334 - Ya Tu Sabe
In this episode, the vibe is lively as the boys enjoy a Mixed Berry Mojito. They kick things off with a rant about how every Walmart trip seems to cost an arm and a leg. The conversation then takes a turn as they discuss Mexico's call for its citizens to return home. Amidst the laughs, they touch...
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Daily Insomnia Episode 333 - Karaoke Bros
In this episode, the crew were sipping on the cool, refreshing Eastside cocktail. The boys dive into how the start of summer is cooling things up in the Chicago comedy scene, a couple of karaoke bros, belting out their favorites. The conversation gets historical as they debate who the best…
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Daily Insomnia Episode 332 - Bear Attack
In this episode, the crew sipped on the "Run Conejo Run" cocktail. The boys dive into, Ramon's latest endeavor—the Cast Away diet.Gammal contemplates his odds in the wild, debate who would win: a bear or a lightsaber? The trend of faking anger for internet fame and so much more...
About this show
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.
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