Stand-up comedian Kirsten Michelle Cills joins us for one of the most honest conversations we’ve had about where comedy really comes from. From growing up memorizing stand-up albums in the back seat of her mom’s car to finding her voice on stage, she talks about how she developed a dark, self-aware style that pulls directly from real life. We dive into her early experiences in theater school, what it felt like realizing she wanted to pursue stand-up full time, and how her family reacted when she told them she was becoming a comedian.

The conversation takes a deeper turn as Kirsten shares how living with cystic fibrosis shaped her perspective, her writing, and ultimately her comedy itself. She explains why some of her earliest material came from confronting mortality head-on, how humor became a way to process fear, and what it’s like navigating the grind of the comedy world while carrying very real stakes. Along the way, we also bond over a shared love of horror movies, swapping thoughts on what makes the genre work, why it resonates so deeply, and how dark storytelling connects back to comedy in unexpected ways. It’s a raw, funny, and surprisingly thoughtful look at how life’s darkest realities can fuel some of the most powerful comedy.

New episodes every Monday.

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Check out Kirsten -

Instagram: https://www.instagram.com/kircomedy

Website: https://www.kirstenmichelle.com

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🍸 Cocktails with Dimples and The Beard

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Singer-songwriter Caitlin Cannon joins us for a conversation that swings between funny, uncomfortable, and unexpectedly heavy in the best way. We talk about how her songs often hide jokes inside darker truths, why meaning in her writing shifts as the story unfolds, and how learning to do less vocally completely changed the way she writes and records. Caitlin walks us through the ideas behind her album Love Addict, her relationship with faith and desire, and why some of her songs tend to make people squirm before they make sense.

Things also take a turn into the deeply personal, as Caitlin opens up about writing a song from her incarcerated brother’s perspective and how music became the only way she could tell the truth about something that big. It’s a loose, honest conversation about art, discomfort, and where songs really come from — with plenty of laughs along the way — and one that slowly reveals just how much weight can live underneath humor.

New episodes every Monday.

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Check out Caitlin -

Instagram: https://www.instagram.com/caitlincannonmusic

Website: https://www.caitlincannonmusic.com/

🥃 Official Spirits Sponsor – Great Lakes Distillery

Website: https://greatlakesdistillery.com/

Instagram: https://www.instagram.com/greatlakesdistillery

🎲Episode Sponsor - FU The Game

Instagram: https://www.instagram.com/fu_thegame

Website: https://futhegame.com

T-Shirts provided by Nifty 50 Apparel -

Website: https://nifty50apparel.threadless.com/

🍸 Cocktails with Dimples and The Beard

YouTube: https://www.youtube.com/@cwdatb

Instagram: https://www.instagram.com/cwdatbpodcast/

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A trip to Belize gave us everything you want from a vacation — sunshine, good food, relaxing moments, and just enough confidence to believe everything was going great. Then it gave us the kind of return trip that makes you question your decision-making skills, your patience, and whether flying is even worth it anymore.

On this episode, Dimples, The Beard, and Judy break down the highs and the absolute lows of the trip. From genuinely great moments and unexpected highlights to a massage situation that did not play out the way it was presented, the episode slowly slides from “this was amazing” into “how did we get here?”

Things really go off the rails once it’s time to come home. Missed connections, late-night cancellations, packed airports, bad line choices, and a series of airline decisions that feel almost personal turn what should have been a normal travel day into a full-blown endurance test. Confidence disappears, tempers flare, and optimism dies in real time.

In this episode, we talk about:

Why the Belize trip was actually incredible… at first

* A massage plan that came with expectations and immediate disappointment

* How traveling together exposes dynamics you can’t ignore

* Airport chaos, line strategy, and the false belief that you’re in control

* The slow realization that some trips are cursed on the way home

* The exact point where patience officially ran out

New episodes every Monday.

Subscribe, like, and drop a comment — it really helps the show.

🥃 Official Spirits Sponsor – Great Lakes Distillery

Website: https://greatlakesdistillery.com/

Instagram: https://www.instagram.com/greatlakesdistillery

🎲Episode Sponsor - FU The Game

Instagram: https://www.instagram.com/fu_thegame

Website: https://futhegame.com

🍸 Cocktails with Dimples and The Beard

YouTube: https://www.youtube.com/@cwdatb

Instagram: https://www.instagram.com/cwdatbpodcast/

Facebook: https://www.facebook.com/CocktailswithDimplesandTheBeard

X: https://twitter.com/dimplesthebeard

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📧 For sponsorships or collaborations: cwdatb@gmail.com