The brand new Southern Gentlemen Hat is officially available! CLICK HERE if you'd like to pick one up and support the show.

Things get a little closer to home in this episode of the Southern Gentlemen Podcast as Chris and Winston take on a round of “Would You Rather”—but this time, the questions come straight from their kids. From silly dilemmas to surprisingly thoughtful curveballs, the guys do their best to keep up with the next generation’s creativity. Just when they think they’re in the clear, their wives sneak in a few of their own questions—guaranteeing some laughs, a little mischief, and maybe even a bit of marital payback. Grab a seat on the porch and join in the fun as family puts these Southern Gentlemen in the hot seat.

Subscribe, share, and don’t forget — stay Southern, y’all.

The brand new Southern Gentlemen Hat is officially available! CLICK HERE if you'd like to pick one up and support the show.

Chris and Winston dive into I Hope You’re Happy, the new album from BIGXTHAPLUG, and unpack what makes it one of the most talked-about releases of the year. They highlight the surprising country artists featured on the record and debate whether this bold mash-up of sounds can truly be called “country music.” Is it a fresh chapter in the genre’s evolution or something else entirely? Tune in as the Southern Gentlemen put their Southern spin on this genre-bending conversation.

Subscribe, share, and don’t forget — stay Southern, y’all.

The brand new Southern Gentlemen Hat is officially available! CLICK HERE if you'd like to pick one up and support the show.

In this episode of the Southern Gentlemen Podcast, Chris and Winston dive into a hilarious - and maybe a little frustrating - interaction that Chris recently had with ChatGPT. He asked the AI to turn a photo of Winston into “the most Southern image ever”… and the technology flat-out refused. That moment sparks a bigger conversation between the guys about whether AI carries hidden biases against Southerners and Southern culture. Is it harmless programming, or is there something deeper going on when technology doesn’t quite “get” the South? With their trademark humor and curiosity, Chris and Winston explore the tension between modern tech and timeless Southern identity, asking the question: can a machine ever truly understand sweet tea, front porches, and SEC football?

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In this episode of the Southern Gentlemen Podcast, Chris Thomas and Winston Cruze dive headfirst into one of the South’s most spirited debates: which states really belong in the South, and which ones just can’t claim the title. From Florida’s split personality to the eternal question of Texas pride, the guys break it all down with their signature mix of humor, history, and good ol’ Southern common sense. Expect plenty of laughs, a few hot takes, and maybe even a surprise or two about where the Mason-Dixon line really matters. Grab your sweet tea and settle in—it’s about to get regional!

Watch the YouTube version!

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This week, Chris Thomas and Winston Cruze pull up their rocking chairs and dig into one of the South’s most beloved - and now most controversial - institutions: Cracker Barrel. From rocking chairs on the front porch to hashbrown casserole on Sunday mornings, the Barrel has always been a Southern staple. But lately? Well, let’s just say some of their recent brand changes have folks scratching their heads (and not because of the peg game).

Chris and Winston break down what’s happening inside those country stores, how the company is shifting its image, and whether the fried okra still tastes the same. Expect laughs, hot takes, and maybe even a few stories about their own Cracker Barrel memories. Grab a biscuit and join the conversation - this is one you won’t want to miss.

Watch the video version on YouTube!

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In this episode of the Southern Gentlemen Podcast, hosts Chris Thomas and Winston Cruze dig into the world of college athletics and NIL. Winston shares details from a recent meeting he attended with The Volunteer Club—a Knoxville-based collective dedicated to supporting University of Tennessee student-athletes and fans through Name, Image, and Likeness (NIL) opportunities. He breaks down what he learned about the current landscape of NIL, how it’s shaping the future of college sports, and what it really means for both players and programs. Chris and Winston also share their own perspectives on how NIL could impact traditions, recruiting, and the Southern culture around college athletics. Then they answer a question from a listener from Norway who is planning an upcoming road trip through the American South.

If you’ve ever wondered how NIL is changing the game, this episode offers an inside look with plenty of laughs and Southern perspective along the way.

Subscribe, share, and don’t forget — stay Southern, y’all.

Subscribe, share, and don’t forget — stay Southern, y’all.

In this episode of the Southern Gentlemen Podcast, hosts Chris Thomas and Winston Cruze are back with a jam-packed show full of Southern charm, curious discoveries, and exciting announcements.

First up, they reveal the official list of retail partners now carrying the first ever Southern Gentlemen Camo Hat! Complete list below. Then they announce some brand-spankin'-new ways you can connect with the show, including - drumroll please - a toll free phone number. That’s right, we’ve gone full Southern Gentlemen Hotline.

Chris shares some stories from a recent family trip to the county fair — think fried food, long lines, and questionable rides — then Winston dives into his latest unexpected find while flipping an old house: sealed antique whiskey bottles. Yep, it's like something out of a dusty Southern time capsule.

Watch the video version on YouTube!

Got a question for The Gentlemen?
Email: holler@southerngentlemen.com
Call and leave a voicemail: (833) 623-3768 ext. 806

Wanna pick up a Southern Gentlemen Camo Hat? Hit up one of these fine retail establishments.

Alabama (Ashley Mercantile, Deep South Mercantile, Southern General)
Georgia (Blue Ridge Cotton Company)
Tennessee (Ted's Sporting Goods, The Male Room Brotique, White's Mercantile)
Texas (Oxbow General Store, Tyler Kingston Mercantile)

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Subscribe, share, and don’t forget — stay Southern, y’all.