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

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

Comedians - and husband-and-wife duo - Sarah Halstead and Rich Chassler, bring their love of great beverages to every conversation. Each episode features a guest from the worlds of entertainment, wine, food or culture, as Sarah and Rich dive into their stories over a drink (or two). Interesting, funny, and always a little unruly, it's the podcast where comedy meets conversation...and it's always happy hour somewhere.

Episodes

January 20, 2026 46 mins

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'...

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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 ...

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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 ...

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In this episode of 'Drinking During Business Hours', hosts Sarah Halstead  and Rich Chassler welcome comedian and content...

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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.

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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...

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November 26, 2025 46 mins

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 adventure...

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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.

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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.

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November 3, 2025 37 mins

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 ...

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April 15, 2024 40 mins

Sarah and Rich are back for their first show as a married couple! On this special edition, it is time to pop the champagne as the newlyweds welcome the man behind the music at their fabled nuptials! Robby Helperin runs Spotlight Music, an incredibly unique and amazing company that supplies insanely skilled musicians for weddings and other events. Hear about the wedding, a big hurdle Sarah and Rich faced heading into the event, and ...

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March 25, 2024 74 mins

Sarah and Rich welcome comedian, animal rights advocate, and super-entrepreneur Katie Cazorla to the cellar for a conversation as opulent as a fine Cabernet! Get big laughs as Katie shares stories about her French speaking father, pregnancy, and opening up her own comedy club. Plus, get excellent tips on how to be a true friend to animals and why you should never hitchhike in Elmira, NY! Cheers!

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March 11, 2024 64 mins

On this episode, Sarah and Rich welcome comedian Tom Thakkar to the cellar for an in-depth conversation about the comedy scene! Tom shares his perspective on the differences between doing comedy in L.A., New York, and the Midwest. Also, how dark is too dark? No, we're not talking about a pinot noir...get insight into Tom's sense of humor, his process, and how he has tweaked some material when he realized it was maybe a little too r...

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February 26, 2024 57 mins

Sarah and Rich welcome K-Earth 101's Greg Simms for a chat about his culinary exploits on his @grubwithgreg social accounts and some good nosh! Rich, Sarah, and Greg also gab about modern oldies stations, how Greg broke into the radio business, and so much more! Roll your sleeves up and get ready for some big bites on this food and wine edition of DDBH! Cheers!

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February 12, 2024 58 mins

Sarah and Rich are zoomin' back into the cellar and this time they welcome comedian and primatologist Natalia Reagan to the show! Find out about Natalia's unique spin on the science of comedy by implementing science comedy. Also, hear about some harrowing tales involving car crashes and animal attacks! This is an absolute blast of an episode with one of the most fascinating comedians out there today! Cheers!

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January 29, 2024 26 mins

As Dry January comes to a close, Sarah and Rich sit down to discuss the most dangerous couple's activity in the known world...wedding planning! Find out what Sarah and Rich are doing to prepare for the big day, what's coming up at the next big Bottle Shock Comedy show, and why the wedding cake business is completely out of control. Cheers!

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January 15, 2024 49 mins

It may be "Dry January," but the fun continues down in the cellar, as this week comedian/writer/producer Zooms in to chat with Sarah and Rich! Find out how Peter got to work on (arguably) the greatest sitcom ever, with stories from behind the scenes during his time on Seinfeld. Also, get another high-level comedy talk, as Sarah, Rich, and Peter discuss differences in approach to the craft when it comes to young comedians and some o...

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January 1, 2024 64 mins

This week, Sarah and Rich kick off the new year by welcoming with comedian/writer/actor, Garrick Bernard to talk standup and what it is currently like in some of TVs best writer's rooms. Grab a drink and go behind the scenes on some of TV's biggest shows as Garrick gives us a glimpse into writing for Solar Opposites, Star Trek: Lower Decks, and Rick and Morty. Also, if you want a thorough comedy chat, Sarah, Rich, and Garrick talk ...

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December 19, 2023 42 mins

It's the holiday season and this week, Sarah and Rich are down the cellar sharing a glass and some laughs about wedding planning, the perils of doing comedy on the road, and lovely little holiday party at the Hollywood Improv. Also, find out why Rich is a sucker for a sappy Christmas movie. Let the wine flow under the mistletoe on this holly jolly edition of Drinking During Business Hours! Cheers and happy holidays!

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December 4, 2023 56 mins

The wine flows, the jokes fly, and things get kind of "grapey" on this edition of Drinking During Business Hours, as Sarah and Rich welcome Claude Stuart to the show! Claude explains what it was like growing up in Mississippi and dreaming of getting into comedy, how he broke into the business, and how he actually is living the dream, raising a family and supporting them through his comedy. Plus, you will find out all about Claude's...

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