Mateen Stewart Gets Real on Comedy, Rejection & Bigger Doors
Release Date: 06/29/2026
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info_outlineMateen Stewart Gets Real on Comedy, Rejection & Bigger Doors
In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler welcome comedian, actor, and producer Mateen Stewart for a hilarious and wide-ranging conversation over BuzzBox cocktails. The episode kicks off with sports fandom, Detroit pride, Knicks talk, and the emotional damage of being a lifelong Lions fan before shifting into Mateen’s path through acting, theater, summer camps, and eventually stand-up comedy.
As the conversation unfolds, Mateen shares how a simple goal to try three minutes at an open mic turned into a full comedy career, along with stories about comedy classes, bringer shows, ticket-selling pressure, and the strange realities of the stand-up business. Sarah, Rich, and Mateen also dig into what makes comedians relatable, why life experience matters on stage, and how the industry keeps changing with streaming, social media, and audience habits.
The episode lands on a personal and inspiring note when Mateen talks about losing his mother, the wisdom she gave him, and how her phrase “Bigger Doors” became the title of his special. Funny, honest, and packed with insight about show business, persistence, and creative life, this is a great episode for comedy fans, entertainers, and anyone trying to build a career in the arts.
Guest Info
Mateen Stewart is a Detroit-born stand-up comedian and actor who studied theater at Florida A&M University. Public sources credit him with screen appearances tied to Last Week Tonight with John Oliver, Jimmy Kimmel Live!, and acting credits including Comics Unleashed, Comedy Parlour Live: Quarantine Edition, The Devil Comes to Kansas City, and NTSF:SD:SUV::. In the episode, Mateen also plugs his special Bigger Doors, available on YouTube.
Guest Social Links
Instagram: @mateenstewart … https://www.instagram.com/mateenstewart/
X / Twitter: @MateenStewart … https://x.com/MateenStewart
Facebook: Mateen Stewart Comedy … https://www.facebook.com/mateenstewartcomedy/
Linktree: linktr.ee/mateenstewart … https://linktr.ee/mateenstewart
Drink of the Podcast
This episode features BuzzBox premium ready-to-drink cocktails, starting with a Vodka Cranberry, then moving to Whiskey Lemonade, and finishing with the Mardi Gras Hurricane. Sarah and Rich describe the boxed cocktails as recyclable, portable, and surprisingly strong with a shoutout to Kevin from BuzzBox for supplying the drinks.
Chapters
00:00 Welcome back to Drinking During Business Hours
01:30 BuzzBox cocktails and what everyone is drinking
03:22 Introducing Mateen Stewart
03:35 Detroit sports, Knicks fandom, and Lions heartbreak
09:30 Summer camps, Long Island, and counselor life
17:32 From acting auditions to discovering stand-up comedy
21:50 Comedy classes, bringer shows, and first stage highs
27:47 Success, comedy credits, and industry respect
30:20 Bad networking, comedy etiquette, and checking in with the host
35:10 Social media, ticket sales, and the changing stand-up business
40:20 Third cocktail pour and Mateen’s theater background
42:55 Wedding DJing, officiating, and using life in comedy
46:15 Losing his mother and the meaning behind Bigger Doors
50:45 Writing scripts, pitching projects, and handling rejection
55:20 Detroit loyalty, LA life, and hometown identity
57:55 Where to find Mateen and upcoming road dates
59:10 Final thank-yous, plugs, and outro
Call to Action
If you enjoyed this episode, be sure to like, comment, and subscribe to Drinking During Business Hours on YouTube. Share the episode with a comedy fan, drop your favorite Mateen Stewart moment in the comments, and follow Sarah and Rich for more funny, unfiltered conversations with comics, creatives, and culture people over a drink or two.
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Rich
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Podcast
Apple Podcasts: Drinking During Business Hours … https://podcasts.apple.com/us/podcast/drinking-during-business-hours-with-sarah-halstead/id1273935631
YouTube: @DrinkingDuringBusinessHours … https://www.youtube.com/@DrinkingDuringBusinessHours
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