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Keith Reza on Comedy, Fame, and Never Giving Up

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

Release Date: 07/28/2026

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More Episodes

Keith Reza on Comedy, Fame, and Never Giving Up

This week on Drinking During Business Hours, Sarah Halstead and Rich Chassler sit down with comedian, actor, writer, and podcaster Keith Reza for a funny, candid, and inspiring conversation about building a career in comedy, staying persistent in entertainment, and carving out your own voice in a brutally competitive business.

With roots in stand-up, a long-running podcast of his own, and years spent learning from the legendary Norm Macdonald, Keith brings the kind of behind-the-scenes perspective comedy fans love.

From the grind of live comedy to storytelling, podcasting, industry survival, and the mindset it takes to keep going, this episode is a great listen for comics, creators, and anybody chasing a creative life. If you love conversations about stand-up, entertainment, mental resilience, and the reality behind making it, this one belongs on your watchlist.

 


 

🎤 Guest Info

Keith Reza is a stand-up comedian, actor, writer, and podcast host with more than 20 years in comedy. He was diagnosed with Asperger’s Syndrome at 13 and found comedy as a way to connect with people and navigate the world. He was mentored by Norm Macdonald for nine years, contributed as a writer on Norm Macdonald Has a Show and Norm Macdonald Live, has appeared on NBC, Animal Planet, and Netflix Is A Joke, and released the special Keith Reza: Make It Happen. He also hosts the long-running celebrity interview podcast Reza Rifts.

 


 

đź”— Guest Social Links

 


 

🍷 Drink of the Podcast

Drink of the Podcast: Molto Bene Mocktails

Whether it’s wine, cocktails, or something unexpected, the drink always sets the tone on Drinking During Business Hours, where comedy, conversation, and happy hour energy always meet in the middle.

⏱️ Chapters

00:00 Intro to Keith Reza

02:15 Keith’s comedy journey

06:40 Learning from Norm Macdonald

11:05 Writing, performing, and finding your voice

16:20 The reality of stand-up life

22:10 Hosting Reza Rifts

28:35 Comedy, resilience, and mental toughness

35:00 Entertainment industry lessons

42:25 What keeps comedians going

49:10 Final thoughts and where to follow Keith

📣 Call to Action

If you enjoyed this episode, make sure you like, comment, and subscribe to Drinking During Business Hours for more conversations with comedians, actors, writers, and creatives from across entertainment and culture.

Drop a comment with your favorite Keith Reza moment and share the episode with someone who loves stand-up comedy, podcasts, and behind-the-scenes industry stories.

🥂 Host Links

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


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