From Teen Dad to Touring Comic: Willie Macc on Pain, Parenting & Punchlines

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From Teen Dad to Touring Comic: Willie Macc on Pain, Parenting & Punchlines What happens when comedian Willie Macc sits down with Sarah J Halstead and Rich Chassler over a killer bottle of wine? You get one of the funniest, rawest, and most unexpectedly heartfelt episodes of Drinking During Business Hours. In this episode, Willie opens up about becoming a father at 16, building a career as a commercial actor, choosing the uncertain road of stand-up comedy, and why he's betting on himself now more than ever. The conversation dives into parenting, religion, mental health, growing up under strict rules, being on the autism spectrum, and how pain can become powerful comedy material. They also talk about Willie's upcoming special "Good Dad, Bad Father," his relationship with his son, comedy club politics, and why the long road might be the real road. If you like comedy podcasts with real depth, big laughs, and zero fake energy, this episode is for you. Guest Info Willie Macc is a comedian, writer, actor, father, and "problem solver," with his official site calling him "Your New Favorite Storyteller." His X bio describes him as going "From BET College Hill to the commercial king and touring comic." In the episode, Willie also shares that his special Good Dad, Bad Father is headed to Amazon Prime in July. https://www.williemacc.com/ Social Links * Willie Macc Website: https://www.williemacc.com/ [https://www.williemacc.com/] * Willie Macc X: https://x.com/funnywilliemacc [https://x.com/funnywilliemacc] * Willie Macc Facebook: https://www.facebook.com/imwilliemacc/ [https://www.facebook.com/imwilliemacc/] * In-episode handle/spelling: "Willie Mack on everything" — W-I-L-L-I-E M-A-C-C Willie Macc Official Site [https://www.williemacc.com/] X [https://x.com/funnywilliemacc] https://www.genspark.ai/api/files/s/umvPVLFa Drink of the Podcast 2017 Michel Chapoutier Costieres de Nimes A Rhône blend discussed in the episode as including Grenache, Syrah, Mourvedre, Cinsault, and Carignan. Sarah frames it as a special bottle from the cellar, opened because Willie is a guest they genuinely wanted to celebrate. https://www.genspark.ai/api/files/s/umvPVLFa Chapters 00:00 Intro, new glasses, upcoming shows 03:22 Opening the wine and welcoming Willie Macc 07:59 The casting advice that changed Willie's commercial career 09:39 Why Willie is choosing stand-up over comfort 12:24 Becoming a dad at 16 and the origin of Good Dad, Bad Father 16:47 Religion, preacher-family pressure, and hard questions about faith 25:20 Willie's son, parenting, and autism 36:43 Fathers, grandparents, discipline, and what changes over time 43:38 The stand-up grind and comedy club politics 46:20 Mental health, dark thoughts, and staying in the fight 48:20 Braille, perspective, and Willie's dark comedy film idea 50:20 Questions for God, upcoming special, socials, and outro Drink of the Podcast 2017 Michel Chapoutier Costieres de Nimes A Rhône blend discussed in the episode as including Grenache, Syrah, Mourvedre, Cinsault, and Carignan. Sarah frames it as a special bottle from the cellar, opened because Willie is a guest they genuinely wanted to celebrate. Host Links FOLLOW US ON SOCIALS! Sarah IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en [https://www.instagram.com/sarahhalstead/?hl=en] FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/ [https://www.facebook.com/sarahjhalsteadcomic/] X @sarahjhalstead https://twitter.com/sarahjhalstead [https://twitter.com/sarahjhalstead] Website @SarahHalstead [https://instagram.com/sarahhalstead] | sarahjhalstead.com [https://sarahjhalstead.com/] Rich IG @richchassler https://www.instagram.com/richchassler/ [https://www.instagram.com/richchassler/] FB @chasslerfans https://www.facebook.com/Chasslerfans/ [https://www.facebook.com/Chasslerfans/] X @richchassler https://x.com/richchassler [https://x.com/richchassler] Website richardchassler.com [https://richardchassler.com/] https://richardchassler.com/ 📧 drinkingduringbusinesshours@gmail.com 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know! Enjoyed the episode? Like, subscribe, and share it with a comic, actor, or podcast fan who'd appreciate a real conversation about stage time, social media, comedy hustle, and taking creative risks. #DrinkingDuringBusinessHours #WillieMacc #SarahHalstead #RichChassler #PodcastClips #ComedyPodcast #StandUpComedy #GoodDadBadFather #ComedyLife #SingleDadStories #Fatherhood #EntertainmentPodcast #ComedianInterview #DarkComedy #BehindTheLaughs #PodcastRecommendations #ComedyFans #WineAndComedy #FunnyAndRaw #BetOnYourself

She Did Fallon While Raising Twin Boys?! | Jessica Keenan on Comedy, Motherhood & Chaos

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. https://www.genspark.ai/api/files/s/b2H1n5BI 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. https://www.genspark.ai/api/files/s/b2H1n5BI 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. https://www.genspark.ai/api/files/s/b2H1n5BI 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/ [https://www.jkeenancomedy.com/] Instagram: @jkeenancomedy … https://www.instagram.com/jkeenancomedy/?hl=en [https://www.instagram.com/jkeenancomedy/?hl=en] Website: jkeenancomedy.com [https://www.jkeenancomedy.com/] … https://www.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. https://www.genspark.ai/api/files/s/b2H1n5BI 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 https://www.genspark.ai/api/files/s/b2H1n5BI 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. https://www.genspark.ai/api/files/s/b2H1n5BI 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. https://www.genspark.ai/api/files/s/b2H1n5BI FOLLOW US ON SOCIALS! YouTube Channel: https://www.youtube.com/@DrinkingDuringBusinessHours Sarah IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en [https://www.instagram.com/sarahhalstead/?hl=en] FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/ [https://www.facebook.com/sarahjhalsteadcomic/] X @sarahjhalstead https://twitter.com/sarahjhalstead [https://twitter.com/sarahjhalstead] Website @SarahHalstead [https://instagram.com/sarahhalstead] | sarahjhalstead.com [https://sarahjhalstead.com/] Rich IG @richchassler https://www.instagram.com/richchassler/ [https://www.instagram.com/richchassler/] FB @chasslerfans https://www.facebook.com/Chasslerfans/ [https://www.facebook.com/Chasslerfans/] X @richchassler https://x.com/richchassler [https://x.com/richchassler] Website richardchassler.com [https://richardchassler.com/] https://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

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From Teen Dad to Touring Comic: Willie Macc on Pain, Parenting & Punchlines

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