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

She Did Fallon While Raising Twin Boys?! | Jessica Keenan on Comedy, Motherhood & Chaos In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler welcome comedian, writer, actress, mother, and now homeowner Jessica Keenan for a hilarious and refreshingly honest conversation about stand-up comedy, motherhood, ambition, marriage, wine, and trying to keep your identity intact while juggling all of it. The episode opens with a playful conversation about launching the show on YouTube, dealing with comments online, and a passionate breakdown of the featured wine before the hosts bring Jessica into the mix. Once Jessica joins the conversation, the episode quickly becomes one of those classic Drinking During Business Hours hangs where funny stories and real talk bounce off each other effortlessly. Jessica talks about recently moving closer to the clubs after years of brutal driving, her husband's finance job at a wire manufacturing company, her roots in Las Vegas, and how speech and debate helped shape the performer she would eventually become. She also gets into how she fell in love with stand-up, why classes helped her commit to the craft, and how chasing that first great set feels a lot like gambling. The conversation gets even richer when Jessica opens up about being a comedian with identical twin boys, balancing life on the road with motherhood, and how comedy fits into family life. Sarah, Rich, and Jessica also dive into the realities of women in comedy, late-night TV pressure, outfit panic before The Tonight Show Starring Jimmy Fallon, hair and makeup anxiety, true crime obsession, sleep habits, and the strange overlap between ambition and everyday chaos. It is funny, candid, and full of the kind of chemistry that makes this podcast feel like being at the table with them. Guest Info Jessica Keenan is a stand-up comedian, writer, and actress who has performed in high-profile comedy rooms across Los Angeles and beyond. In this episode, Sarah and Rich talk with Jessica about her comedy journey since starting stand-up in 2012, her background in speech and debate, her experience performing on The Tonight Show Starring Jimmy Fallon, and what it means to stay active and relevant in comedy while raising young twin boys. Jessica comes across as sharp, self-aware, grounded, and seriously funny. She talks openly about the hustle of the business, the importance of balance, and why she never wanted comedy to become the kind of life that prevented her from actually living. That perspective gives this episode a really strong center beneath all the jokes. Guest Social Links Jessica Keenan … https://www.jkeenancomedy.com/ Instagram: @jkeenancomedy … https://www.instagram.com/jkeenancomedy/?hl=en Website: jkeenancomedy.com … https://www.jkeenancomedy.com/ Drink of the Podcast Sangiovese from Tuscany, Italy This week's featured wine is a Sangiovese from Tuscany, Italy. Sarah describes it as transparent in color, Pinot Noir-like at first glance, but unmistakably Sangiovese once you taste it and see the orange rim. She highlights its beautiful red fruit profile, darker brooding undertones from age, and the fact that it works both with food and on its own. The hosts even joke that it is light enough to enjoy with an ice cube by the pool. The producer and vintage are not stated in the episode. Chapters 00:00 Welcome back and YouTube channel shoutout 01:56 The reality of comments, haters, and playing to camera 02:08 Wine intro: Sangiovese from Tuscany, Italy 03:50 Why good bottles should be opened now, not saved forever 04:35 Introducing Jessica Keenan 08:14 Moving closer to the clubs and years of brutal LA driving 09:48 Jessica's husband, finance, and the mysterious smell of wire 15:24 Comedy rooms, lineups, and women in stand-up 15:38 How Jessica got started in stand-up and speech/debate roots 26:04 Motherhood, identical twin boys, and balancing comedy with family life 35:03 Marriage, dating comics, and finding the right partner 35:13 Jessica's Tonight Show with Jimmy Fallon story 39:11 The pressure of outfits, hair, makeup, and late-night TV presentation 48:44 Sleep habits, meditation music, and true crime at bedtime 54:43 Twin boys, attention, and whether the kids inherited the funny 57:43 Where to follow Jessica, Sarah, Rich, and subscribe to the show's YouTube Call to Action If you loved this episode, make sure you subscribe to the Drinking During Business Hours YouTube channel, give the episode a thumbs up, and leave a comment telling Sarah and Rich what you thought preferably a good one, as they jokingly note at the top of the episode. You can also follow Jessica Keenan on Instagram and keep up with her live dates on her website. If this episode hit for you, share it with a friend who loves stand-up comedy, parenting chaos, late-night TV stories, wine talk, and unfiltered conversations. FOLLOW US ON SOCIALS! YouTube Channel: https://www.youtube.com/@DrinkingDuringBusinessHours Sarah IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/ X @sarahjhalstead https://twitter.com/sarahjhalstead Website @SarahHalstead | sarahjhalstead.com Rich IG @richchassler https://www.instagram.com/richchassler/ FB @chasslerfans https://www.facebook.com/Chasslerfans/ X @richchassler https://x.com/richchassler Website richardchassler.com 📧 drinkingduringbusinesshours@gmail.com 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know! #DrinkingDuringBusinessHours #JessicaKeenan #JKeenanComedy #SarahHalstead #RichChassler #ComedyPodcast #StandUpComedy #WomenInComedy#MomComedian #TwinMom #JimmyFallon #TonightShow #WineAndComedy #YouTubePodcast #ComedianInterview

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 nonprofit dedicated solely to the financial, mental health, and recovery needs of stand-up comedians, Zoe's life is a master class in turning a legacy into a lifeline. This episode is a rich, warm, and illuminating conversation about the business behind the laughs, the people who make comedy possible, and why giving back to the comedy community isn't just important, it's essential. Guest Bio Zoe Friedman is a Los Angeles-based comedy executive, co-founder of Comedy Gives Back, and one of the entertainment industry's most respected behind-the-scenes forces. The daughter of Budd Friedman, who opened the first comedy club in America The Improvisation in New York City in 1963, Zoe literally grew up in the greenrooms and bar stools of stand-up history, rubbing shoulders with Richard Pryor, Jay Leno, Andy Kaufman, and Jerry Seinfeld before most kids knew what a punchline was. Zoe launched her professional career as a talent booker and producer for the Late Show with David Letterman (1992–2000), helping shape one of the most iconic comedy platforms in television history. She then moved to Comedy Central as Director of Development, rising to VP of Development & Original Programming, before consulting for Jimmy Kimmel Live! (2012–2014) as a comedian development specialist earning the nickname "the Comic Whisperer" for her rare ability to connect with and develop stand-up talent. In 2010, alongside co-founders Amber J. Lawson and Jodi Lieberman, Zoe co-founded Comedy Gives Back the only 501©(3) nonprofit dedicated exclusively to stand-up comedians. The organization has granted over $1 million to more than 1,000 comedians, providing financial crisis relief, mental health therapy (in partnership with Didi Hirsch Mental Health Services), and chemical dependency treatment. She is also a co-producer of The Improv: 50 Years Behind the Brick Wall, a documentary featuring Jay Leno, Jerry Seinfeld, and Judd Apatow. Connect with Zoe Instagram: @wowiezowie … https://www.instagram.com/woweezowie Facebook … https://www.facebook.com/zoefriedman Website … comedygivesback.com … https://comedygivesback.com/ Chapters 0:00 Opening, podcast growth milestones, host check-in 3:02 Wine story and guest introduction welcoming Zoe Friedman 5:48 Legacy of comedy: growing up at The Improv, Budd Friedman's founding story 11:26 The evolution of comedy how the industry has shifted over decades 17:15 Business dynamics in comedy: booking, deals, and personal reflections 22:52 Childhood aspirations, early influences, and formative comedy memories 28:29 The currency of laughter what comedy means as a cultural force 30:15 The craft of stand-up: what makes a great comedian 32:22 The evolution of comedy and its modern challenges 35:12 Behind the scenes of comedy booking (Letterman, Kimmel, Comedy Central) 37:15 The importance of opportunity discovering and developing comedians 41:09 Comedy Gives Back: origin story, mission, and what the org provides 47:24 Supporting comedians in crisis mental health, financial relief, recovery 50:05 Building a sustainable future for the comedy community Projects & Resources Mentioned Project / Resource Description Link Comedy Gives Back 501©(3) nonprofit — financial relief, mental health & recovery for comedians comedygivesback.com Entertainment Community Fund Support org for actors & entertainment workers entertainmentcommunity.org MusicCares Music industry equivalent of Comedy Gives Back musiccares.org Calls to Action 🌐 Visit comedygivesback.com to learn more, donate, or apply for support 🎭 Encourage your local comedy clubs to partner with Comedy Gives Back's Club Network 🤝 Share resources and CGB information with struggling comedians in your network ❤️ Follow & support Zoe: @wowiezowie on Instagram | Facebook 🍷 Featured Beverage Wine for this episode — pair it with a conversation worth savoring. 🎙️ Hosts 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 Website @SarahHalstead | sarahjhalstead.com Rich IG @richchassler https://www.instagram.com/richchassler/ FB @chasslerfans https://www.facebook.com/Chasslerfans/ X @richchassler https://x.com/richchassler Website richardchassler.com 📧 drinkingduringbusinesshours@gmail.com 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know! #DrinkingDuringBusinessHours #ZoeFriedman #ComedyGivesBack #TheImprov #BuddFriedman #StandUpComedy #ComedyPodcast #MentalHealth #Philanthropy #LettermanShow #ComedyCentral #GivingBack

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 Sarah J. Halstead and Rich Chassler welcome a familiar face to the DDBH couch: LA-based comedian, actor, and podcast host Doug Bass. 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 their most embarrassing stories, and what it really takes to survive and thrive in the entertainment industry. GUEST Doug Bass is a stand-up comedian, actor, director, and podcaster based in Los Angeles, originally from Cedar Grove, New Jersey. He trained at The Groundlings, UCB, and IO West, performs regularly at major LA clubs including the Hollywood Improv, and has appeared on national television and in commercials. Doug is the creator and host of The Basshole Show a live stand-up and storytelling experience turned hit podcast where comedians, actors, celebrities, and everyday people share their best a**hole stories, get roasted and judged, and then try to redeem themselves. Past performers on the live show include Jo Koy, Kevin Hart, John Mulaney, Tom Arnold, Mary Lynn Rajskub, Jamie Kennedy, Alonzo Bodden, Kimiko Glenn, Brittany Furlan, and Mindy Sterling. He also owns and operates Basshole Podcast Studio in West Hollywood, a fully equipped recording space available to independent podcasters. Connect with Doug: 🌐 bassholeshow.com 🎧 Basshole with Doug Bass on Spotify 🎧 Basshole with Doug Bass on Apple Podcasts 📸 Instagram: @dougbasshole 📸 Show Instagram: @bassholeshow CHAPTERS 00:00 Introduction and Personal Updates 01:15 Milestone: First Monetized Episode 02:20 The Role of Basshole Studios in Success 03:18 Guest Introduction: Doug Bass 06:57 The Basshole Show: Concept and Evolution 08:34 COVID-19 Impact and Podcast Growth 10:43 On the Road: Touring the Show 12:35 Building a Podcast Studio at Hollywood Improv 14:25 Challenges of Podcasting and Monetization 16:10 Celebrity Podcasts and Industry Trends 18:23 Balancing Acting and Diversification 20:05 Wine Tasting and Storage Insights 22:18 The Art of Wine Collecting and Cellaring 25:57 Doug Bass: From Theater to Entertainment 27:44 Lessons from Acting and Industry Advice 29:59 The Future of Podcasting and Content Creation 32:00 Closing Remarks and Guest Socials CONNECT W/ THE HOSTS Sarah J. Halstead and Rich Chassler are comedians, podcasters — and husband and wife. Together they host Drinking During Business Hours, where guests from the worlds of entertainment, food, wine, and culture sit down for real conversations over a drink (or two). Their warmth, wit, and genuine curiosity make every episode feel like a night out with your funniest friends. Sarah J. Halstead — @SarahHalstead on all platforms Rich Chassler — @RichChassler on all platforms 📧 Email: drinkingduringbusinesshours@gmail.com DID YOU LOVE IT? Please subscribe, rate, and leave a review wherever you listen — it makes a huge difference and helps Sarah and Rich bring incredible guests like Doug to you every week. And while you're at it, go check out The Basshole Show — you won't regret it. Cheers! 🥂 Drinking During Business Hours — Where Comedy & Fine Wine Meet. #Viral #Trending #FunnyAF #MustListen #PodcastRecommendations #FYP #ForYouPage #Reels #PodcastClip #Funny #Comedy #LOL #TrueStory #RealTal

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 doesn't make you a comedian. The episode touches on everything from vintage cars and Carnegie Hall to the emotional reality of watching your parents age while pursuing your creative dreams. About Adam Ferrara Adam Ferrara is a veteran stand-up comedian, actor, and podcaster who has spent over three decades mastering authentic storytelling across every entertainment platform. Best known for his recurring roles on Nurse Jackie (Netflix), NCIS as "Sloppy Joe Sammy," and Rescue Me, Adam represents the last generation of comics who cut their teeth in mob-run Brooklyn clubs before graduating to Carnegie Hall. His podcast "The Adam Ferrara Podcast" features intimate conversations with guests like Nathan Lane, Ann Wilson, and Billy Gibbons, capturing the warmth of friends laughing around a dinner table. A Long Island native splitting time between LA and NYC's West Village, Adam brings blue-collar authenticity and hard-won wisdom to everything he does—whether sharing his father's life-changing advice ("Do it now, before your life gets complicated"), discussing vintage cars, or explaining why being funny in the copy room doesn't make you a comedian. Connect: @AdamFerrara on all platforms AdamFerrara.com ... http://adamferrara.com/ for tour dates The Adam Ferrara Podcast ... https://podcasts.apple.com/us/podcast/the-adam-ferrara-podcast/id1473543128 on all platforms Chapters 00:00 Welcome to the New Year 02:42 Celebrating Growth and Community 05:27 Bagels and Lox: A Culinary Surprise 08:23 The Life of a Stand-Up Comedian 11:02 Navigating the Acting World 14:03 Memorable Experiences in Comedy 16:47 The Importance of Mentorship 19:29 The Evolution of Podcasting 22:15 Connecting with Celebrities 24:58 Family Influence and Personal Growth 27:39 The Journey of a Stand-Up Comedian 30:23 Reflections on Life Choices 33:17 The Role of Comedy in Coping 36:01 Advice for Aspiring Comedians 38:48 The Changing Landscape of Entertainment 41:50 Final Thoughts and Farewell 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 #adamferrara #topgear #ncis #standupcomedy #comedian

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 Sandra Bullock, and why comedy competitions don't work. Plus: hilarious tales from the Melrose Gelson's, parking lot muggings at the Improv, and why New York summers are unbearable. Whether you're a comedy fan, aspiring comedian, or just love authentic conversations about mental health and show business, this episode delivers laughs and real talk in equal measure. Featured Guest Jeremy Hotz is an internationally renowned stand-up comedian, actor, and former writer for The Daily Show. Known for his neurotic, observational comedy style, Jeremy has performed on Letterman, The Tonight Show with Jay Leno, and starred in the critically acclaimed Canadian series "The Newsroom" (which won multiple awards). His film credits include Speed 2: Cruise Control with Sandra Bullock. Despite living with generalized anxiety disorder, Jeremy has built a thriving international comedy career, recently experiencing viral success on TikTok throughout Africa. He tours extensively in Canada and is planning his first-ever African tour. Jeremy never travels without his emotional support chihuahua, Shaq. Find Jeremy Hotz: Official Website: JeremyHotz.com TikTok: @JeremyHotz (HUGE following in Africa!) Instagram: @JeremyHotz Twitter/X: @JeremyHotz YouTube: Jeremy Hotz Comedy Chapters 0:00 - Welcome Back & Recent Updates 2:50 - Introducing Jeremy Hotz 5:00 - Why Beer Instead of Wine 6:30 - Living with Anxiety & Social Situations 9:15 - Meet Shaq: The Emotional Support Chihuahua 12:20 - The Newsroom & Speed 2 Stories 16:45 - Lucky Break: Episode 13 Award Win 19:30 - Starting Stand-Up at 18-19 22:40 - Getting Letterman & Tonight Show 27:15 - Finding Your Comedy Voice 31:20 - New York vs LA Life 36:50 - Comedy Club Stories & Improv Tales 41:30 - Going Viral on TikTok in Africa 45:20 - Auditions & Industry Advice 49:40 - Television Industry Problems 53:15 - Celebrity Stories & Gelson's Tales 56:30 - Upcoming Tour Dates 58:45 - Final Thoughts & Wrap-Up 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 #JeremyHotz #StandUpComedy #MentalHealthAwareness #ComedyPodcast #AnxietyAndSuccess #TikTokComedian #DrinkingDuringBusinessHours #CanadianComedy #EmotionalSupportDog #LettermanStories

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 life on stage and the challenges of preserving authentic, controversial material in modern theater. Featured Guest Ronnie Marmo - Actor, Writer, Director, and Artistic Director of Theatre 68 (Los Angeles & New York City) IG: @ronniemarmo ... https://www.instagram.com/ronniemarmo/?hl=en X: @realronniemarmo ... https://x.com/realronniemarmo Ronnie Marmo is a bi-coastal theater artist best known for his critically acclaimed portrayal of Lenny Bruce in "I'm Not A Comedian… I'm Lenny Bruce," directed by Joe Mantegna. With over 412 performances to his credit, Marmo has dedicated himself to keeping Bruce's legacy alive and relevant. As Artistic Director of Theatre 68, he creates spaces for bold, meaningful theatrical experiences while teaching acting classes internationally via Zoom. Chapters 00:00 - Introduction and Guest Introduction 02:52 - Theater and Performance Insights 05:58 - Lenny Bruce's Legacy and Impact 08:42 - Navigating Controversial Material 11:42 - Personal Journey and Career Development 14:17 - Theater Group and Community Engagement 17:20 - Audience Reactions and Performance Challenges 19:56 - Cultural Relevance of Lenny Bruce Today 22:52 - Final Thoughts and Future Projects 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 @ https://x.com/richchassler #lennybruce #standupcomedy #ronniemarmo

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 content creation. Check out Mitsy on Socials IG @mitsysanderson https://www.instagram.com/mitsysanderson/ TikTok @mitsy270 https://www.tiktok.com/@mitsy270 Chapters 00:00 Introduction and Holiday Cheer 02:49 Guest Introduction: Mitzi Sanderson 05:41 The Journey of a Content Creator 08:29 Navigating Social Media and Stand-Up Comedy 11:20 The Impact of the Pandemic on Careers 14:02 The Evolution of Comedy and Female Representation 16:42 The Competitive Nature of Comedy 19:39 Future Aspirations and Projects 22:26 Closing Thoughts and Social Media Presence #mitsysanderson #comedian #dancer #podcast

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.