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!

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. BUY TICKETS

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 it happen. Plus, what does the perfect pre-show day look like for Kev? Oh—and Ramon reads Gammal’s eulogy. Yeah, you read that right. Real laughs, real love, and so much more. 
Buy tickets to Kevin's Kevin and Hell album tape for this Saturday August 9th 9pm at Lincoln Hall!! TICKET: lh-st.com/shows/08-09-2025-windy-city-comedy-festival-late

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 wide-ranging episode.

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 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.