Advertise on podcast: 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 madness surrounding the tournament. Mexico started partying days before the opening whistle, Korea seems to be having the time of their lives in Mexico, Scotland somehow took over Boston, and Canada... where are you guys? They also break down the biggest pros and cons of World Cup 2026 and what fans can expect when the world's biggest sporting event comes to North America. Plus, don't forget—Demon Hour Comedy returns July 10th at 9 PM, and we're upgrading the show once again. Grab your tickets now on Eventbrite. All that and so much more in this week's episode!

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 but love. They talk about the special’s premiere at The Lincoln Lodge, Kevin’s journey leading up to this moment, and everything that went into making it happen. The boys also recap their trip to C2E2, where the Chicago Pope stole the show and even won a balloon popping contest. Kevin in Hell drops April 1st on YouTube — don’t miss it. And of course, so much more.

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 what they’re expecting from it. Real talk, wild stories, and plenty more in this one!

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, building momentum, staying consistent—without losing the artist you were when you first picked up an instrument. We also get into what makes them unique: Charming Ritual is basically three bands combined into one, which explains the sound, the chemistry, and the way they write and perform. It’s music talk, origin stories, and lessons you can steal for your own creative grind… and at the end, Charming Ritual leaves a special treat for everyone listening.

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 unborn baby chicken?). From there it turns into bedtime talk: the weird, specific things we each need to actually fall asleep, and why our brains refuse to shut off. Then we roast the winter nightlife struggle—getting dressed up just to fight traffic, pay cover, and tip a dollar for someone to hand you paper towels in the bathroom like it’s a luxury service. That leads to the bigger question: is the bar/club scene slowly getting killed, and if so, by what—prices, vibes, age, phones, crowds, all of it? We end up looking in the mirror asking the most important question of the night: ARE WE THE NEW TIOS?! and so much more.

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 vs. Red 40 Hot Cheetos and which one is actually better, plus the question nobody asked but everyone has an opinion on—do robbers go for newer cars or beat-up old trucks? We wrap it all with Pope energy in full gear for Bears tailgating, and plenty more along the way.

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 little details that separate a solid night from a great one. We debate the question every producer argues about: is 7:00 PM a perfect time slot, or is it too early for people to really be ready to laugh? Kat takes it left with her “perfect man is blind?!” theory, and then we get into a real moment—four years sober? It’s funny, honest, and a strong start to the year… and we definitely go plenty of other places too.

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 and Andrew Tate both taking losses—how it happened, what it says about hype vs. substance. They wrap with a heartfelt thank you to everyone who supported Daily Insomnia Podcast and Demon Hour Comedy this year for 2025 also special appearance... and so much more. Demon Hour Comedy this Friday: BUY TICKETS!

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 for fans. Big theme of the night: you can’t just stack ideas; you’ve got to move on them. We cap it off with the hype: this Wednesday is Paper Cardinal’s first headlining show as a full group at the Cobra Lounge Chicago—and there’s plenty more where that came from. Grab a drink and enjoy this episode with us.

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 over the past year, drops 30 minutes of Spanish content for the fans, and keeps the laughs rolling with plenty more stories and insights along the way!

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 wild listener calls in this week’s “We’re Listening, Chicago” segment, and so much more!  This Friday, 9pm Demon Hour Comedy at the Lincoln Lodge Chicago. BUY YOUR TICKETS!!

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 treat their patrons better. The guys also debut a brand-new segment, “We’re Listening, Chicago,” where listeners call in and answer the boys’ wild questions. All that and plenty more laughs, drinks, and chaos in this one! If you'll like to be a caller, follow us on instagram or tiktok Daily Insomnia Podcast for our questions and call 312.967.2551 to leave your voicemail answer to our questions. Thanks yall!

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 game, nothing is off limits. The conversation gets even spicier with talk of escort pricing in Chicago, the boys’ own kinks and search histories, and plenty more chaos along the way.

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 laughs, hot takes, and plenty of chaos. Demon Hour Comedy this Friday BUY TICKETS

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 Rambo and Phil hilariously explain who Oasis even is), to the nightmare of workplace hazing — this episode packs laughs, stories, and plenty more.  Demon hour Comedy this August 22nd 9:30pm: BUY TICKETS!