The Grind of Comedy with Dean Delray

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Release Date: 01/20/2026

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

The Grind of Comedy with Dean Delray In this episode of “Drinking During Business Hours,” hosts Sarah J Halstead and Rich Chassler sit down with veteran comedian and podcaster Dean Delray for an honest, inspiring conversation about the comedy hustle. Fresh from a memorable road trip complete with incredible food stops (including the legendary Rose’s Cantina in El Paso), the hosts dive deep into Dean’s journey through the stand-up world. Dean shares the story behind his groundbreaking new comedy special “5836,” filmed in a Tennessee cave, and discusses why self-production has become...

The Legacy of Lenny Bruce with Ronnie Marmo

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

The Legacy of Lenny Bruce with Ronnie Marmo Join hosts Sarah Halstead and Rich Chassler in a captivating conversation with actor, writer, and Artistic Director Ronnie Marmo as they explore the enduring legacy of legendary comedian Lenny Bruce. This episode delves deep into the world of boundary-pushing comedy, the art of performance, and why Bruce’s revolutionary work remains vital in today’s cultural landscape. Marmo, who has performed his acclaimed one-man show “I’m Not A Comedian… I’m Lenny Bruce” over 412 times, shares intimate insights into bringing this iconic figure to...

From Acting to Award-Winning Director: Jamie Anderson on 30 Years in Hollywood, Meditation & Making Provocative Art

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Jamie Anderson explores the journey of transitioning from acting to directing, the importance of joy in creative work, and the power of networking in the film industry. They discuss the role of meditation in maintaining mindfulness and creativity, as well as the significance of creating provocative art that sparks conversation. Jamie shares insights into her upcoming projects and the creative process, emphasizing the importance of relationships and doing what makes you happy. Where to Watch: Me Too Nice (short film) - Available on Amazon Prime Follow Jamie: Instagram:...

From Dance to Comedy: Mitsy Sanderson's Journey

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

In this episode of 'Drinking During Business Hours', hosts Sarah Halstead and Rich Chassler welcome comedian and content creator Mitsy Sanderson. The conversation explores the journey of Mitzi from her early aspirations in dance and fashion to her rise as a viral sensation on social media. They discuss the impact of the pandemic on creative careers, the competitive nature of comedy, and the representation of women in the industry. Mitzi shares her experiences with stand-up comedy, the challenges of maintaining relevance in the digital age, and her future aspirations in acting and...

Dr. Bronner's, Two Cats, and One Very Slippery Situation

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Sarah and Rich recount their cats' Dr. Bronner's slip-and-slide disaster, reveal new stand-up tour dates, confront a surprise social media troll (hi, Dad), and debate whether deer are overpopulated or just losing real estate. Comedy, chaos, and questionable wildlife facts - all in one glass of Cabernet Franc.

The One-Liner King: Brian Kiley on Conan, Letterman & the Oscars

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Comedian and one-liner master Brian Kiley joins Sarah and Rich over yummy mocktails to share stories from his decades-long career. He's written for Conan O'Brien, performed on David Letterman and Jay Leno, and crafted jokes for the Academy Awards. With 16 Emmy nominations and one win, plus a viral Dry Bar Comedy special, Brian reveals the art of crafting punchlines that land, performing clean, razor-sharp comedy while staying fresh across a legendary career in late-night TV and stand-up.

Dan Dunn: The Story Behind the Stories

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Sarah and Rich welcome celebrated writer, journalist, and raconteur Dan Dunn, whose compelling persona has made him a standout in books, podcasts, and storytelling everywhere. Dan reflects on some of the most memorable moments of his career: his appearance on Conan O'Brien with a mouthful of bacon, his time writing for Playboy, and the inspiration behind his bestselling book, American Wino, including the behind-the-scenes adventures of traveling across the country exploring America's wine regions. He also shares his soft spot for Texas wineries - fearless, bold, and larger than the state...

Pregnant, Poured, and Unfiltered: Lucia Ford on Sips, Sommelier Life and the CIA

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Join Sarah and Rich as they sit down with the very pregnant and wildly charming "affordable Sommelier" Lucia Ford. From what a sommelier can actually drink while expecting to her CIA training and content-creator life, Lucia keeps the laughs-and the mocktails-flowing...and proves why she still out-tastes everyone in the room.

Drinking During Dojo Hours with Cobra Kai's Dan Ahdoot

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Sarah and Rich pour laughs and glasses with Cobra Kai's own Dan Ahdoot for a conversation that's equal parts comedy, wine, and "no mercy." They talk about why Dan is moving back to New York, dining adventures with Ralph Macchio, and even the secrets of "inside wine trading." Grab a glass, settle in, and join them for a mix of comedy, storytelling, and great wine - with a splash of mischief.

We're Back!

Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

After a long (and much-needed) hiatus, Sarah Halstead & Rich Chassler return to the mic - married, refreshed, and with more stories than ever. In this comeback episode, the newlyweds spill everything: why they pressed pause, what life on the road as a two-comedian household is really like, and how they've been juggling love, laughter, and learning how to rest in a world that never slows down. They also dive into their latest drink obsessions - what they're sipping, why it's in their glass, and how much it costs! From newlywed bliss to comedy chaos to the art of day-drinking...

More Episodes

The Grind of Comedy with Dean Delray

In this episode of “Drinking During Business Hours,” hosts Sarah J Halstead and Rich Chassler sit down with veteran comedian and podcaster Dean Delray for an honest, inspiring conversation about the comedy hustle. Fresh from a memorable road trip complete with incredible food stops (including the legendary Rose’s Cantina in El Paso), the hosts dive deep into Dean’s journey through the stand-up world. Dean shares the story behind his groundbreaking new comedy special “5836,” filmed in a Tennessee cave, and discusses why self-production has become essential in today’s entertainment landscape. This episode is packed with hard-earned wisdom, hilarious stories, and a raw look at what it takes to survive

FEATURED GUEST

Dean Delray - Stand-Up Comedian, Podcaster, and Host of “Let There Be Talk”

IG @deandelray https://www.instagram.com/deandelray/

X @deandelray https://x.com/deandelray?lang=en

Website https://www.deandelray.com/

Podcast Let There Be Talk https://podcasts.apple.com/us/podcast/dean-delrays-let-there-be-talk/id546210508

Dean Delray is a veteran stand-up comedian known for his authentic, high-energy performances and his popular podcast Let There Be Talk, where he interviews fellow comedians, musicians, and artists. With decades of experience grinding it out on the road, Dean represents the true working comedian, someone who’s built a career through relentless perseverance, authenticity, and an unwavering love for the craft. His latest special “5836” showcases his unique approach to comedy production and his commitment to doing things his own way.