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.

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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?

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