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

How a Comedy Legacy Shapes Today’s Industry: Zoe Friedman’s Mission

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

How a Comedy Legacy Shapes Today’s Industry: Zoe Friedman’s Mission Hosts Sarah J. Halstead and Rich Chassler sit down with Zoe Friedman, comedy industry veteran, co-founder of Comedy Gives Back, former Late Show with David Letterman talent booker, and daughter of legendary Improv founder Budd Friedman. Zoe didn’t just grow up around comedy she grew up inside it, doing cartwheels on stage during Andy Kaufman’s Children’s Cabarets and getting homework help from Richard Pryor at the bar. From talent booking at Letterman to VP of Development at Comedy Central to co-founding the only...

I Don’t Want to Be Strong Today: Vanessa Graddick, The Social Worker Who Became a Comedian

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

I Don’t Want to Be Strong Today: Vanessa Graddick, The Social Worker Who Became a Comedian Hosts Sarah J. Halstead and Rich Chassler sit down with the brilliantly funny and deeply thoughtful Vanessa Graddick, comedian, producer, social worker, and now published author. Vanessa opens up about starting comedy on November 1, 2006, after her mother’s cancer diagnosis, serving Allen Iverson at Applebee’s, performing for troops across Kuwait, Iraq, Afghanistan, South Korea, and Japan, and why she believes every human being should be required to work in a restaurant for 90 days. The...

We’ve All Been One - Doug Bass Gets Real

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

We’ve All Been One - Doug Bass Gets Real Grab your favorite glass and pull up a chair this week, comedians and husband-and-wife duo and welcome a familiar face to the DDBH couch: LA-based comedian, actor, and podcast host . You may remember Doug from when Sarah and Rich were guests on his show The Basshole Podcast — in what Doug himself called “the first time a married couple has ever graced the show.” Now the tables are turned, the wine is poured, and Doug is spilling everything about building a comedy brand from the ground up, the art of getting people to share...

My Dad’s in Jail, My Girlfriend Left Me, and I Became a Comedian: The Arturo Vaca Story

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

My Dad’s in Jail, My Girlfriend Left Me, and I Became a Comedian: The Arturo Vaca Story In this fresh and funny conversation, hosts Sarah J. Halstead and Rich Chassler welcome rising comedian and viral content creator Arturo Vaca for an honest, hilarious deep-dive into the unlikely road from the Valley to the comedy stage. Born and raised in Van Nuys, Arturo’s path to stand-up wound through teenage delinquency, a short-lived skateboarding career, two years of MMA fighting (including a trip to Thailand), and the kind of hard family circumstances that either break you or become your best...

Adam Ferrara on Comedians, Carburetors & Carnegie Hall: A Working-Class Hero's Guide to Showbiz

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

Adam Ferrara on Comedians, Carburetors & Carnegie Hall: A Working-Class Hero's Guide to Showbiz In this heartfelt and hilarious conversation, veteran stand-up comedian and actor Adam Ferrara joins hosts Sarah J. Halstead and Rich Chassler for a deep dive into the entertainment industry, family influences, and the art of survival in show business. From performing at mobster-run comedy clubs in Brooklyn to landing recurring roles on major network shows, Adam shares candid stories about his Italian-American upbringing, his father's life-changing advice, and why being funny in the office...

From Magic Castle to Broadway: Michael Shayan’s Journey as The Gay Persian Who Plays His Own Mother

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

In this delightful and heartfelt conversation, hosts Sarah J. Halstead and Rich Chassler welcome Emmy-nominated actor, writer, and magician Michael Shayan for an engaging discussion about family, identity, theater, and the transformative power of storytelling. From his early days as a 12-year-old magician at the Magic Castle to his critically acclaimed one-man play about his Persian mother, Michael shares his remarkable journey through entertainment with humor, vulnerability, and grace. Michael Shayan - Emmy-nominated writer, actor, and former magician Instagram: ...

Navigating the Comedy Scene with Jeremy Hotz

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

Join hosts Sarah J Halstead and Rich Chassler for a hilarious and honest conversation with legendary Canadian comedian Jeremy Hotz! In this episode, Jeremy opens up about living with generalized anxiety disorder while maintaining a successful comedy career, his viral TikTok explosion in Africa, why he travels with his emotional support chihuahua Shaq, and the real story behind his career-defining moments on Letterman and The Tonight Show. From writing for The Daily Show to starring in the iconic Canadian series "The Newsroom," Jeremy shares behind-the-scenes stories from Speed 2, working with...

The Grind of Comedy with Dean Delray

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:...

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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.