In this episode of Southern Gentlemen, hosts Chris Thomas and Winston Cruze sit down with Alabama-born stand-up comedian Derrick Stroup for a hilarious and heartfelt conversation you don’t want to miss.

The guys dive into how growing up in the South shaped Derrick’s comedic voice, why Waffle House holds a special place in his heart (plus his exact go-to order), and how he almost stole a girl from country music star Riley Green. Things get real when Derrick opens up about his past DUIs and how those tough experiences became the unlikely launchpad for his career in comedy.

Watch the video version on YouTube!

This episode is packed with laughs, redemption, and a whole lot of Southern charm.

To learn more about Derrick, visit https://derrickstroupcomedy.com!

Connect with Chris and Winston online at https://thesoutherngentlemen.com!

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#SouthernGentlemenPodcast #DerrickStroup #Comedy #WaffleHouse #SouthernHumor #Redemption #Podcast

Ever wondered what the heck cryptocurrency is but felt like all the explanations were made for tech geeks and Wall Street bros? Well, we’ve got you covered. In this episode of the Southern Gentlemen Podcast, Chris Thomas and Winston Cruze sit down with entrepreneur Brett Henry to break down cryptocurrency - Bitcoin, Ethereum, meme coins, and more - in plain English.

Brett explains what the blockchain actually is (without making your head hurt), how cryptocurrency can be used in the real world, and what steps to take if you’re curious about getting started. Whether you're skeptical, confused, or just looking for a good story about the wild world of digital money, this episode is for you.

Grab a drink, pull up a chair, and let’s talk Crypto for Rednecks.

To learn more about Brett Henry, visit https://deco.how.

Don't forget to LIKE the video, SHARE with a fellow redneck, and SUBSCRIBE to the channel!

Watch the video version on YouTube!

Connect with Chris and Winston online at https://thesoutherngentlemen.com!

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#SouthernGentlemenPodcast #Obituaries #Funny #Humor #Comedy

In this episode of the Southern Gentlemen Podcast, Chris Thomas and Winston Cruze dive into the world of real-life obituaries - some heartfelt, some downright bizarre, and others so funny you won’t believe they’re real. From a woman who was declared one of Waffle House's most loyal customers to a Kentucky man remembered for his fondness of "hammering beers," these final farewells prove that a great sense of humor can live on even after we're gone.

Get ready for laughter, unexpected wisdom, and maybe even a few ideas for how you want to be remembered (hopefully not anytime soon). Grab a drink, sit back, and enjoy the ride.

Subscribe for more conversations on life, legacy, and a little bit of southern charm!

Watch the video version on YouTube!

Connect with Chris and Winston online at https://chrisandwinston.com!

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#SouthernGentlemenPodcast #Obituaries #Funny #Humor #Comedy

In this special episode of Southern Gentlemen, Chris Thomas and Winston Cruze sit down with a guest they’ve never met before - and they know nothing about him! Welcome to Unexpected Company.

Their guest? Michael Farren, an award-winning songwriter from Columbia, Tennessee. Michael shares his journey from growing up in Texarkana, Texas, to chasing his dream in Nashville’s songwriting scene. He opens up about the struggles that nearly cost him his marriage and the lessons he’s learned along the way. Plus, he introduces Chris and Winston to his latest adventure - Bourbon Gospel.

It’s a raw, real, and unfiltered conversation filled with surprises, laughter, and a few deep moments of reflection. Pull up a chair, pour a glass of something good, and join the conversation.

Learn more about Michael Farren and The Bourbon Gospel.

Watch the video version on YouTube!

Subscribe, like, and share if you enjoy the episode!

Connect with Chris and Winston online at https://chrisandwinston.com!

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#SouthernGentlemenPodcast #UnexpectedCompany #MichaelFarren #BourbonGospel #NashvilleSongwriting #TexarkanaRoots

Get ready for an all-out battle of wits (or lack thereof) as Chris Thomas and Winston Cruze go head-to-head in a no-holds-barred Dad Joke showdown! 🏆😂 In this episode of Southern Gentlemen, the fellas take turns delivering the corniest, groan-worthiest, and most side-splitting Dad Jokes they can muster—all while trying to keep a straight face.

Will Chris hold his composure? Will Winston finally break? And will any of these jokes actually be funny? (Spoiler: Absolutely.)

Join us for a full episode of laughter, bad puns, and timeless Southern charm. Don’t forget to like, comment, and subscribe if you love a good Dad Joke!

Watch the video version on YouTube!

📢 Tell us your best Dad Joke in the comments! 👇

Connect with Chris and Winston online at https://chrisandwinston.com!

📲 Follow Us: Instagram | Facebook | TikTok | Patreon

#DadJokes #SouthernGentlemenPodcast #ChrisAndWinston #DadJokeChallenge #TryNotToLaugh

In this episode of Southern Gentlemen, Chris Thomas and Winston Cruze get real about the American South - the good, the bad, and the downright ridiculous. From the food, the music, and the legendary hospitality to the brutal humidity and the ever-present "fake people" (you know the type), nothing is off-limits.

Chris and Winston break down their favorite southern traditions, the artistry and craftsmanship that make the region special, and the quirks that drive them crazy. Whether you're a proud southerner or just curious about life below the Mason-Dixon, this episode is sure to entertain.

Pour yourself some sweet tea (or maybe something a little stronger) and join the conversation!

Watch the video version on YouTube!

💬 What do YOU love or hate about the South? Drop a comment below!

Connect with Chris and Winston online at https://chrisandwinston.com!

📲 Follow Us: Instagram | Facebook | TikTok | Patreon

In this episode of the Southern Gentlemen Podcast, hosts Chris Thomas and Winston Cruze dive into the importance of prioritizing overnight dates with their wives. They share how taking time away - just the two of them - helps strengthen their marriages, deepen their connection, and keep the spark alive.

Chris and Winston also explore some of their favorite spots for the perfect overnight date in Nashville and Franklin, TN, from cozy boutique hotels and hidden gem restaurants to unforgettable experiences that make for a meaningful getaway. Whether you're looking for inspiration for your next date night or just want to hear some good conversation about love, commitment, and southern hospitality, this episode is for you.

Watch the video version on YouTube!

Subscribe, listen, and let us know—what’s your ideal overnight date?

Connect with Chris and Winston online at https://chrisandwinston.com!

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#MarriageMatters #SouthernGentlemenPodcast #DateNightIdeas

In this episode of Southern Gentlemen, Chris Thomas shares the story of changing the oil in his wife’s car - something he hadn’t done in over 30 years! He and Winston Cruze dive into the lost art of basic car maintenance, swapping stories and sharing practical tips for handling the essentials. From the must-have tools to the mindset shift that comes with taking on a hands-on task, this conversation is all about self-sufficiency, learning new (old) skills, and embracing the satisfaction of a job well done.

They also take a moment to talk about a big setback—the Southern Gentlemen YouTube channel was deleted. Yep, gone. And now, they’re starting completely from scratch. Chris and Winston share what happened, what they’ve learned from the experience, and how you can help them rebuild.

Whether you're a seasoned DIYer or someone who's never popped the hood, this episode will inspire you to roll up your sleeves and tackle something new. Grab a glass of sweet tea (or a shop rag), and join us for a fun and insightful discussion!

🔧 Topics Covered:

• Why Chris decided to change his own oil after 30+ years
• Essential tools for basic car maintenance
• Tips for first-timers (and what NOT to do!)
• The value of learning hands-on skills in today’s world
• What happened to the Southern Gentlemen YouTube channel—and how you can help us rebuild!

Watch the video version on YouTube!

📢 Help us rebuild! If you enjoy the show, please subscribe to our new YouTube channel, like the video, and share it with a friend. Every bit of support means the world to us!

🎧 Subscribe and tune in for more conversations on thriving as a man - mind, body, and spirit - all through the lens of timeless Southern values.

Click here to see a list of the tools Chris used to change the oil on his wife's car!

Connect with Chris and Winston online at https://chrisandwinston.com!

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#SouthernGentlemenPodcast #CarMaintenance #DIY #OilChange #SouthernValues #Rebuilding

In this episode of Southern Gentlemen, Chris Thomas and Winston Cruze share the daily and weekly rituals that bring value and joy to their lives. From the perfect morning coffee routine to weekly chiropractor visits and even the best way to wash a truck, they discuss the small traditions that make a big difference. Plus, they dive into the Male Bag to answer a listener’s question: What are the best trucks to buy without breaking the bank? 🚛💰

🔹 Simple rituals that add meaning to everyday life 🔹 Chris & Winston’s go-to habits for well-being 🔹 Practical truck-buying advice for budget-conscious buyers

What’s a ritual that makes your life better? Drop it in the comments!

🎧 Subscribe for more conversations on thriving as a man - mind, body, and spirit - rooted in timeless Southern values.

Watch the video version on YouTube!

Connect with Chris and Winston online at https://chrisandwinston.com!

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Valentine’s Day is around the corner, and Chris Thomas and Winston Cruze are here to help you navigate it like a true Southern Gentleman. In this episode, they share how they approach Valentine’s Day with their wives, from meaningful traditions to thoughtful gift ideas. They also cover some major Valentine’s Day pitfalls - like gifts you should definitely avoid! Whether you’re planning something special or need a last-minute save, this episode has you covered.

Hit play and make this Valentine’s Day one to remember (for the right reasons)! And don’t forget to subscribe for more episodes of Southern Gentlemen.

Watch the video version on YouTube!

Connect with Chris and Winston online at https://chrisandwinston.com!

Instagram | Facebook | TikTok | Patreon