The Grind of Comedy with Dean Delray episode artwork

EPISODE · Jan 20, 2026 · 46 MIN

The Grind of Comedy with Dean Delray

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

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. CHAPTERS 00:00 - Welcome Back and Road Trip Tales 02:43 - Introducing Dean Delray 04:56 - Dean's New Special: 5836 10:15 - The Grind of Comedy and Perseverance 19:31 - Influences and Early Days in Comedy 29:16 - Navigating the Industry and Staying Authentic 39:02 - Closing Thoughts and Future Plans   FOLLOW US ON SOCIALS! Sarah IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en  FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/ X @sarahjhalstead  https://twitter.com/sarahjhalstead  Rich IG @richchassler https://www.instagram.com/richchassler/ FB @chasslerfans https://www.facebook.com/Chasslerfans/ X @richchassler https://x.com/richchassler    #StandUpComedy #Comedian #ComedyPodcast

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The Grind of Comedy with Dean Delray

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This episode was published on January 20, 2026.

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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...

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