You probably didn’t have "Post Malone and Dwight Yoakam riding horses down Sunset Boulevard" on your 2024 bingo card. Honestly, who did? But there they were, decked out in enough rhinestones to blind a passing motorist, filming a video for a track that marks a weirdly perfect collision of two different eras.
It’s easy to dismiss this as just another Post Malone side quest. The guy has spent the last year collecting country music legends like they’re Pokémon. From Dolly Parton to Blake Shelton, he’s checked off almost every major box in Nashville. But the connection with Dwight Yoakam feels different. It’s deeper than a marketing play.
The Song That Wasn’t on F-1 Trillion
When Posty dropped F-1 Trillion in August 2024, people were scouring the tracklist for Dwight’s name. It wasn't there. A lot of fans were actually pretty bummed out about it. They’d seen the two of them jamming together on Dwight’s SiriusXM show years ago, and the chemistry was undeniable.
As it turns out, the collaboration was saved for something more personal. Dwight Yoakam released his first album of new material in nine years, Brighter Days, on November 15, 2024. The centerpiece? A song called "I Don't Know How To Say Goodbye (Bang Bang Boom Boom)."
Dwight didn't just ask Post to hop on a verse. He wrote the song specifically for him. That's a huge deal. Yoakam is notoriously meticulous about his "Bakersfield Sound"—that sharp, honky-tonk rock that doesn't usually play nice with modern pop production. By writing a duet specifically for Post Malone, Yoakam effectively gave him the highest seal of authenticity you can get in the "rebel" wing of country music.
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Why Do They Even Get Along?
On paper, it makes zero sense. One is a 68-year-old pioneer of neo-traditionalist country who wears hats so low you can barely see his eyes. The other is a 30-year-old global superstar with face tattoos who got famous singing "White Iverson."
But if you look at their history, the friendship actually goes way back.
- 2018: Post appeared on Dwight Yoakam & The Bakersfield Beat on SiriusXM. They covered "A Thousand Miles from Nowhere." Post looked genuinely terrified and thrilled at the same time.
- April 2024: Post brought Dwight out during his Stagecoach set to perform "Little Ways."
- July 2024: Posty made a surprise appearance at the Greek Theatre in LA. They ripped through "Guitars, Cadillacs" and "Fast As You."
The common thread is a genuine love for the craft. Post Malone has been a country "superfan" since he was a kid in Texas. He didn't just wake up one day and decide to buy a Stetson. He’s been playing these covers in dive bars since before he was famous. Dwight, who has always been a bit of an outsider in the Nashville machine, clearly recognizes that "outsider" spirit in Post.
Breaking Down the "Bang Bang Boom Boom" Video
The music video for "I Don't Know How To Say Goodbye" is a fever dream of California country. Directed by Gregory Alosio, it features the duo in Hollywood, looking like they stepped out of a 1970s Nudie Cohn catalog.
It’s not just the two of them, either. The video is packed with random celebrity cameos like Nina Dobrev and Malin Akerman. It’s flashy, it’s expensive, and it’s arguably the most "Dwight" thing to happen to music in a decade. The song itself is a twangy two-stepper. It doesn't try to be a hip-hop crossover. There are no programmed drums. It’s just pure, unadulterated Bakersfield twang.
The Impact on Post Malone's Career
A lot of people thought Posty's country era would be a one-and-done thing. "He's just bored," the critics said. But by aligning himself with Dwight Yoakam, he’s moving away from the "Pop-Country" label and into the "Americana/Roots" world.
Think about the artists on F-1 Trillion. Most are modern chart-toppers. But Dwight represents the history. He represents the grit. By being the only guest on Dwight’s first album in nearly a decade, Post Malone isn't just a guest; he’s a protégé.
Some of the old-school fans are still skeptical. You can see it in the Reddit threads. They worry the "country guitar strings" don't hit the same as the trap beats. But then you see him on stage with a guy like Dwight, and it’s hard to deny the talent. The guy can actually sing. And more importantly, he knows the words to the deep cuts.
What This Means for Country Music in 2026
We are seeing a massive shift in how genres work. The "Post Malone effect" has opened the door for more genre-fluidity than ever before. If a guy can go from "Rockstar" to a Dwight Yoakam duet without losing his fan base, the old rules are officially dead.
Dwight’s album Brighter Days proved he’s still got the "cool" factor. He’s 68 and still the sharpest guy in the room. By bringing Post into his world, he’s ensured that a whole new generation of kids who grew up on streaming services will actually know what the Bakersfield Sound is.
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Next Steps for the Fan:
- Listen to the Lyrics: Go back and listen to "I Don't Know How To Say Goodbye" alongside "Guitars, Cadillacs." You’ll hear how Dwight tailored the melody to fit Post’s vibrato while keeping his own signature "hiccup" style.
- Watch the Live Clips: Search for their 2018 SiriusXM session. It’s the rawest version of their collaboration and shows the foundation of their friendship before the big budget videos.
- Check the Credits: Look at the production on Brighter Days. It was self-produced by Yoakam and mixed by Chris Lord-Alge. It’s a masterclass in how to make a record sound "old" and "new" at the same time.