Let me start with a confession: I am not a country music fan. I don’t own boots. I’ve never shouted “yeehaw” unironically. My idea of twang involves indie folk bands with banjos and suspiciously clean flannel shirts. So when I queued up James Robert Webb’s Weekend Outlaw, I expected some decent songwriting, a few predictable chord progressions, and lyrics about trucks, whiskey, and heartbreak.
I got all of that. But I also got a hell of a good time.
Webb’s fourth album is something like a love letter to the people who work hard all week and refuse to let life pass them by. It’s big-hearted, rowdy, and a little messy in all the right ways — like a Friday night out with your best friends and a bar tab you definitely shouldn’t have opened. What surprised me most wasn’t the themes (which are pretty country 101), but the energy. This thing moves.
The opener, “Weekend Outlaw,” sets the tone perfectly. There’s a galloping rhythm, crunchy guitars, and lyrics that lean into the fantasy of breaking loose like Jesse James. It’s kind of absurd, kind of awesome, and undeniably catchy. Right away, I got why people love this stuff — it’s music designed for release, for letting go, for stomping your foot a little too hard on a hardwood floor.
https://www.youtube.com/watch?v=-DANrLj-yRo
Track two, “Gentlemen Start Your Weekends,” takes that same idea and blows it wide open. It’s all Friday night adrenaline, complete with a surprisingly natural guest verse from Nashville rapper Classic Williams. It’s the kind of crossover that shouldn’t work but does, mostly because Webb sounds like he’s having the time of his life. And frankly, I started to have some fun too.
What kept me engaged were the moments when the album pulled back. “Ride or Die” is more polished, almost pop-adjacent, with a chorus that wouldn’t be out of place in a Shania Twain setlist. “Lovesick Drifting Cowboy” is pure outlaw drama — all leather jackets, open roads, and emotional wreckage. I rolled my eyes at the title, then found myself mumbling the chorus two hours later.
But Weekend Outlaw isn’t just denim and dust. There’s actual tenderness here, too. “Buenos Noches Nagadoches” is low-lit and dreamlike, with lyrics that go down smoother than the whiskey it probably took to write them. “She’s Not You” is straight-up devastating. It tells the story of someone loved completely by one person while still haunted by someone else. It might be the best song on the album — and yes, I rewound it twice.
Will I become a full-time country convert? Probably not. But Weekend Outlaw showed me a version of the genre that isn’t just about clichés — it’s about freedom, joy, sadness, and living your life loud, even if only on the weekends.
Gwen Waggoner