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If you’re still out here trying to define Sturgill Simpson by genre, I don’t know what to tell you anymore. The man treats genre lines like optional suggestions, and we’re all just blessed to witness the flow.

Case in point… two of the most random, “wait… WHAT?” collaborations you probably forgot about if you ever knew about it at all.

That Time Sturgill, Kesha, and Brian Wilson Shared a Track

Back in 2020, Kesha dropped High Road in the midst of the Covid shutdown, and buried in that tracklist is a song called “Resentment” that hits way harder than anyone expected. The stripped back song reflects on the disappointment and self-doubt following a relationship that just won’t work out, and is honestly one of the most heartfelt tracks our favorite gutter glitter pop princess has ever issued.

And tucked into those harmonies? Sturgill Simpson. Alongside Brian Wilson. Yes, that Brian Wilson.

Listen Here

It’s raw, it’s bitter, and it leans more Americana than pop. That’s exactly why Sturgill fits so naturally. His haunting masculine tenor tone feels like part of the emotional backbone of the track, and it’s a shame that the song didn’t gain more traction while we were all in that moment of forced self-introspection.

Then There’s “Use Me” With Diplo and Dove Cameron

Diplo’s been playing in the country sandbox for a minute now, and one of the more overlooked cuts to come out of that experiment is “Use Me.” The track features Dove Cameron on vocals, bringing a smooth, almost hypnotic pop edge to the whole thing.

And right there in the mix again… Sturgill.

Listen Here

The song rides this strange line between country, pop, and electronic production. It shouldn’t feel grounded. But Sturgill’s involvement gives it just enough grit to keep it from floating off into generic territory.

Dove Cameron carries the melody with that clean, polished vocal, while Sturgill adds texture underneath. It’s subtle, but it matters. It turns what could’ve been a forgettable crossover into something you actually go back and listen to again.

So Why Are People Still Shocked By Sturgill?

Every time Sturgill drops something unexpected, there’s always a wave of confusion.

But honestly… why? This is the same guy who:

• Jumped from outlaw country to psychedelic rock without warning
• Dropped an anime film with Sound & Fury
• Ended projects under his own name to adopt the Johnny Blue Skies persona
• Regularly shows up in projects that have nothing to do with Nashville

So when people act surprised about a disco influence or a pop collab, I kind of just laugh. He’s been doing this.

This right here is what separates artists from artists.

Sturgill doesn’t collaborate for clout. He collaborates because he’s curious. Because he hears something interesting and wants to be part of it. Because it’s FUN. That’s how you end up on a track with Kesha and Brian Wilson one minute… and then sliding into a Diplo-produced song with Dove Cameron the next.I’m not questioning it. I’m pouring a drink and pressing play.

What’s the Weirdest Sturgill Collab You’ve Found?

Because I know there are more.

Drop them in the comments or come argue with me over on Country Music News Blog. I’ll be over here digging through the internet looking for the next “how did this even happen?” moment.

Sidenote: Stay tuned for a Johnny Blue Skies 2026 tour announcement in the next few days 😉

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