Daily Insomnia Podcast

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 alive this time of year. With the World Cup officially kicking off on June 11th, the boys dive into the...

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 — from a heartfelt message from his mom before he hit the stage, to a packed room that showed nothing b...

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, or good people carry a dark past? Plus, the boys break down the Spider-Man: Brand New Day trailer and w...

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 basement parties at U of I Champaign. They break down the real hustle of the rock world—finding shows, b...

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 something that makes outsiders pause (and yes… we ask the question: who is really lining up to eat an unbo...

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 January (and it’s wild to already feel like the year’s been a full season), a serious debate on Naked v...

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 stir the pot. Then it turns into real shop talk: what actually makes a comedy show work and all the li...

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 his adventure: the rooms, the comics, the lessons. Then the boys unpack the headline story—Logan Paul a...

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 released album Jupiter Run, and what really separates an EP from a full album—creatively, strategically, and f...

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 the example for up-and-coming comedians in the scene. The crew reflects on Demon Hour Comedy’s growth o...

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 react to the latest in tech — a new AI robot that can wash your dishes (finally!). Plus, a fresh round of...

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, where the boys discovered that maybe, just maybe, the dancers could use a refresher course on how to tr...

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 endless lists of icks, to how both sides view what makes a date “bad,” to the truth that some women have no...

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 to have, to strip club culture, and even a rabbit hole on the women of the night, this one’s got laugh...

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. From why being personable is the best way to network, to Phil and Shapel Lacey bonding over Oasis (while R...

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 got stories, laughs, and a little heart. Don't forget Demon Hour Comedy next week Friday August 22nd. ...

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 f...

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...

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.

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...

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 Comed...

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, an...

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 musi...

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 d...