If you’ve been a fan of Sturgill Simpson since his first few records, well, my friend, it’s been an interesting journey, to say the least. For starters, you’ve been privy to the inclinations, talents, and various whims, zigs and zags of one of music’s most interesting ramblers. Good ol’ country music, a dab of bluegrass, hollerin’ shit-kicking barnburners, fuzzy ass guitar rock, and swampy boogie rock are all tools in Simpson’s toolbox, and for that first decade of our time together, these tools were all used at different times. It wasn’t until the past few years that Simpson, under the moniker Johnny Blues Skies, decided to say screw it and use ’em all at once.
It’s been a lot of fun.
Since 2004, Simpson has released and supported music under the name Johnny Blues Skies, backed by The Dark Clouds, a legit wrecking ball of a band that can follow their leader down whatever rabbit hole or back country trail he sets his sights on. Simpson adopted the alias in response to his overall disdain for celebrity and the noise that had started to follow him.
In other words, he just wanted to be a dude in a band, not a solo act.
As Johnny Blues Skies, Simpson has released two albums, 2024’s Passage Du Desir and this year’s Mutiny After Midnight, and has toured relentlessly, hammering out 3-hour shows that pulled from all corners of his catalog and seamlessly incorporated covers from the likes of Prince, The Doors, Allman Brothers Band, and more. The shows have become urban legends, with those attending having emerged telling stories of the greatness they witnessed and those at home, left to wait for the JBS caravan to come to their neck of the woods while they devour live recordings on various streaming platforms and/or social media.
Recently, Johnny Blues Skies and The Dark Clouds kicked off another tour, a tour that Simpson said would be it for a while, citing the need for a break after all the rocking and all the rolling of the past couple of years. The future can often lead to uncertainty, and with Simpson, that is definitely the case given how unpredictable he has become. He once said he would likely hang ’em up after he released five albums, and when The Ballad of Dood and Juanita came out, no one really knew what would be next. But hey, then we got the start of the Johnny Blue Skies era.
So what happens after Mutiny for the Masses Tour is anyone’s guess. But in the meantime, let’s take a beat and go through some of Simpson and company’s best songs.
Optional musical accompaniment can be found here.
30. “In Bloom” (2016)
I know, I know, I know. “In Bloom” isn’t a Sturgill Simpson jawn. Nor is it a Johnny Blue Skies tune. It’s by (checks notes) Nirvana. So with that being said, should it really be included here? Yes, yes it should, and you know why, because Simpson makes this classic song his own. He takes a grunge rock classic and lathers it up with soulful meditation and a soulful musical arrangement, subbing out the angst and distortion for slide guitar and horns. If you’re going to tackle a cover, especially an incredibly well-known one, and you’re then going to try and make it your own, you best be damn sure you can pull it off. Simpson damn sure pulls it off. That’s, uh, that’s for damn sure.
29. “Best Clockmaker on Mars” (2019)
There’s artists taking left turns, and there’s Simpson following up his excellent 2016 album A Sailor’s Guide to Earth with the big rock thrashing goodness of SOUND & FURY. Self-described as a “sleazy synth-rock dance record,” it was about as far removed from alt-country as you could get, which was the point. But it was jarring, and initial reactions were mixed and then discarded because then shit got weird with COVID and the like, and where this record didn’t make much sense at the time, the Cuttin Grass records made tons of sense. But sometimes distance helps, and sometimes taking some under-appreciated, head-scratching tunes out on the road with a kick-ass band really helps. The SOUND & FURY songs have benefited tremendously from the Johnny Blues Skies era, transforming from (checks notes) “sleazy synth-rock dance” to arena-rattling rock monsters.
28. “Make America Fuk Again” (2026)
Hey, we were all enjoying the Johnny Blue Skies live shows, and I don’t think we ever thought the band would hit the studio and attempt to bring the cosmic voodoo they were concocting across the country into the studio, but alas, that’s what happened. Mutiny After Midnight proved to be a wonderful postcard from a wonderful journey, with the foot-stomping “Make America Fuk Again” leading the way.
27. “Long White Line” (2014)
Back in the day, I declared that while I was not a fan of country music, I was very much a fan of what I called “shit-kicking country,” a type of country music that sounds like dust on your boots and tastes like beer in a cold bottle. It’s how I found Sturgill Simpson (as well as artists like Jason Isbell, Drive-By Truckers, among others). It was like lifting up a rock and finding the most glorious rabbit hole ever created by a guitar-strummin’ rabbit. Early Sturgill is chock-full of some shit-kicking country ramblers, with “Long White Line” being one of the best.
26. “Sing Along” (2019)
This song sounds like an army of robots marching across the plains with the intention of leaving no one alive. It’s menacing but also funky, which is weird, but also how I’d explain certain kinds of tacos. “Sing Along” has a stomp that is the stuff of legends and is another tune that has been gifted a fantastic second life on tour. It’s also one of the songs from SOUND & FURY that I was cool with from the jump, and I’ll be honest here and say I was not cool with many of them, whether it was from the jump, a little skip, or skip across the gravestones. But “Sing Along” has an infectious feel to it that makes it undeniable.
25. “Some Days” (2013)
Simpson’s first record, High Top Mountain, is probably his most country-sounding album, mostly due to the fact that it is very much an incredibly country-sounding album. High Top Mountain definitely includes some country-sounding bangers and it’s weird that it’s Simpson’s first record, as it would then lead you to believe it’s the kind of artist he was setting out to be. But if we’ve learned anything, it’s that the kind of artist Sturgill Simpson is setting out to be is a moving target. His records are snapshots of the moment he’s living in, and in 2013, he had recently moved to Nashville and was kicking the tires on some real country-sounding music and country-sounding music is what he found and produced.
24. “Sitting Here Without You” (2013)
“Sitting Here Without You” is another damn good time from that first record. It’s got that special kind of recklessness you find in the bars down on Broadway in Nashville and listening to it, you can hear the stomping on the floor and the slapping of tables and clinking of bottles.
23. “All the Pretty Colors” (2020)
Simpson had been angling to record some bluegrass for a while and, like a lot of us, he took the world stopping for COVID as an opportunity to scratch that itch. Well, sorry. I’m not saying we all started playing bluegrass during COVID. A lot of us baked bread, built pillow forts, and learned how to dress professionally and also comfortably for Zoom calls. But that’s neither here nor there. Simpson released two bluegrass records in 2020: Cuttin’ Grass Vol 1 and Vol 2. The records are mostly made up of reimagined versions of his earlier work with some covers sprinkled in. “All the Pretty Colors” is a wonderful little bluegrass ditty about when your lady leaves you and everything gets bleak but it’s fun here because it’s bluegrass, and any subject matter sounds fun when tackled in a bluegrass kinda way. That’s just science. And probably the banjo and fiddle.
22. “Situation” (2026)
So these songs back-to-back are a fascinating example of how fucking wild Sturgill Simpson’s catalog is. We just did two entries that were bluegrass, and now we go back to the Johnny Blue Skies era where it’s all about that darkly-lit boogie-woogie goodness.
21. “A Good Look” (2019)
I like to peg certain tunes as Good Driving Songs. “Situation” is a good driving song. It’s actually an excellent driving song if I’m being honest. “A Good Luck” could also be a good driving song, provided you were in the midst of a car chase like the ones in that Baby Driver movie. It’s frantically-paced and frantically-played; a certified rush of manic adrenaline that would not be suitable for most driving conditions. Actually, I’d say speeding down a wide-open highway or ramblin’ down a dirt road with a roadie in the cup holder would probably be good moves, but overall, “A Good Look” is too much energy for someone behind the wheel. Safety first, kids.
20. “Mint Tea” (2024)
Passage du Desir was a great reminder of Simpson’s greatness. Not that the Cuttin’ Grass records weren’t great, but they were compilations and had the feel of live albums. So ultimately, we’re talking different vibes here. And then before those albums came out, Simpson released SOUND & FURY, so it had been a minute since we had something really cozy to settle into, which is exactly what Passage du Desir is. “Mint Tea” definitely has Grateful Dead fingerprints on it, a result of Simpson hanging out with Bob Weir down ol’ Mexico way. The tune has a gentleness and laid-back quality that was always present in some Dead songs and leaves room for jamming, which hadn’t always been there in his past work. Simpson’s work. Not Bob Weir’s. You know what I mean.
19. “Go In Peace” (2021)
After the Cuttin’ Grass releases, Simpson seemed to take the bluegrass and vintage country vibes a step further with The Ballad Of Dood And Juanita, which is a record that would fit in nicely on what I assumed AM radio sounded like in the 1970s, especially down south. Like, you could just picture listening to this album sitting behind the wheel of a dinged-up old pickup truck. With the harmonies and the organized musical chaos behind them, “Go In Peace” is what you play for someone who only knows Johnny Blue Skies and you want to provide some background as to who Sturgill Simpson was or is.
18. “Right Kind of Dream” (2024)
Do you ever listen to a song and just sit and think to yourself, “that’s a cool fucking song?” I do. And that’s what I think when I hear “Right Kind of Dream.” The tune has such a sleekness to it and a driving groove. I love how Simpson can really go batshit crazy with hillbilly lunacy on some songs and then Fonzi levels of cool on other songs. And that if he wants to, he can rock the eff out like nobody’s business. But “Right Kind of Dream” is some polished shit, but not in a pretentious way. It just has everything dialed and rowing in the right direction.
17. “Viridescent” (2026)
Viridescent is a word. I didn’t know that and thought it was JBS just fucking around, but no, it means something. But I don’t remember what because I looked it up and then closed the tab. Yeah, I could open the tab back up, but then I would lose my momentum here, writing about looking up the definition of viridescent. That’d be a shame. I think it has something to do with the color green, and that feels like it makes sense. But with that out of the way, I do know that this is one of the strongest songs to come from the JBS Era. It’s sexy, and I don’t normally describe music as sexy, especially Simpson’s music. And the outro is just such a killer bonus. “Viridescent” would be a great three-minute song, but the outro breathes more life into a song that’s already pulsating with life.
16. “Sea Stories” (2016)
Part of the genesis for A Sailor’s Guide to Earth was letters Simpson’s grandfather had written when serving in World War II, letters Simpson said let him learn “more in those three pages about that man than I probably ever could have, like, sitting in a room and talking to him.” Feeling inspired, but also feeling bad about missing so much about his son’s first few months while out on tour, Simpson set out to write his own letters home. Some of the subject matter is pulled from the original letters, but the majority is all Sturgill, with a song like “Sea Stories” having him reflect on his three-year stint in the Navy and the weird years that would follow.
15. “Railroad of Sin” (2013)
I’m not going to rob a bank. I want to make that clear. I mean, it doesn’t really feel like a thing anymore. When was the last time you heard about a bank robbery, let alone a successful bank robbery? It’s probably the cameras or maybe traceable bills. Probably something with DNA, but either way, bank robberies just aren’t what they used to be, although given how things are going, maybe they come back so people can afford to buy gas. But whatever, the point is that IF I were to rob a bank and then jump into the getaway car, I’d be blasting this song as we drove away, successfully eluding authorities. That was the point of that whole thing. It’s a fun song.
14. “Breakers Roar” (2016)
“Breakers Roar” is such a wonderfully tender song off A Sailor’s Guide to Earth, an album I think isn’t just Simpson’s best, but one of the best albums of this century. An album comprised of words of advice to his young son, the record should be required listening for any new parent, as there is no shortage of rock-solid parenting advice and guidance in each song. “Breakers Roar” makes a point of saying that yes, there is disappointment in life, but there is also beauty, and if you simply approach the world with open arms and an open heart, you’ll find that love and beauty and be better off because of it.
13. “Life Ain’t Fair and the World is Mean” (2013)
Literally no one, probably including ol’ JBS himself, knows what Simpson will do next, but if he wanted to go and make a good ol’ country record like High Top Mountain, I don’t think anyone would have an issue with that. And yeah, it can suck to hear, but it’s the truth: “life ain’t fair, and the world is mean.”
12. “I Don’t Mind” (2020)
The Cuttin’ Grass records are good fun for a handful of reasons, but one of them is that they tip listeners off to some of the music from Simpson’s early days, specifically his time with the country rock band Sunday Valley. Simpson got the band together around 2004, took a break for a bit, got them back together a little under a decade later, before electing to set off on his own. Both Cuttin’ Grass albums pull from this period, and one of the high points is “I Don’t Mind,” which becomes a sentimental meditation on loneliness, highlighting the highs and lows of that kind of lifestyle.
11. “Brace for Impact (Live a Little)” (2016)
It feels like there are two main takeaways from A Sailor’s Guide to Earth, with the first being the stuff about the parenting advice and then the second being how just incredibly badass the music is. The music on the album is this delightfully wonderful cocktail of Southern fried, Delta soul, late-stage Elvis, Stax beef, and AM rock radio. “Brace for Impact” is a song that helps create a bridge between 2016 Sturgill Simpson and 2026 Johnny Blue Skies and likely laid the foundation for what this decade had in store for the musician.
10. “Don’t Let Go” (2026)
I was listening to one of the recent Johnny Blue Skies’ shows, and before he kicked off this tune, he said: “It was one for the ladies.” And yeah, that might be true, but goddamn if it doesn’t make me think of my lady and how lucky I am to be married to her. The song just doesn’t resonate; it stirs up something and removes you from whatever the hell you’re currently thinking of and takes you to a happy place and an appreciative place, which sometimes can be hard places to get to. I love that Simpson has this gear, where he can write a song like “Don’t Let Go” that makes you stop dead in your tracks, crack a little smile, and think about that person you love.
9. “Just Let Go” (2020)
“Just Let Go” first appeared on Metamodern Sounds in Country Music, but then got a bluegrass facelift for the first Cuttin’ Grass record. Both versions are great, but I prefer the bluegrass one mainly because it feels like it has more life to it; a bit more soul. The original is fine. It’s just a matter of personal preference, and between you and me, I don’t even really like bluegrass. I appreciate it, but don’t like it. I think it’s the drummer in me and the overall lack of drums in bluegrass. I need a beat; an anchor or foundation. That could change, though. I feel like the older I get, the closer I am to being more of a bluegrass fan. I guess we’ll see.
8. “Call to Arms” (2016)
Simpson was the musical guest on Saturday Night Live about a decade ago, and the performance, which included “Call to Arms” is A) fucking badass B) a preview of the reckless abandon and wild vibes of the Johnny Blue Skies era. Man, if only he brought that horn section out for a show or two on this current tour, huh? Like, maybe at the Brooklyn show. That’d be cool. Oh, and of course, because it’s from A Sailor’s Guide to Earth, there’s some great advice to bestow upon your offspring.
“Turn off the TV/ Turn off the news / There’s nothing to see here / They’re serving the blues / Bullshit on my TV / Bullshit on my radio / Hollywood telling me how to be me / The bullshit’s got to go”
I mean, the song was written over 10 years ago, but it’s still great advice.
7. “Turtles All the Way Down” (2014)
Back when I worked on the boats, I had a captain who lent me a book about Gram Parsons. Now I don’t really listen to Parsons, but there’s something about “Turtles All the Way Down” that reminds me of the Flying Burrito Brothers. I guess it’s because the song feels like such a certain kind of country throwback. It’s not rollicking, but it’s the kind of country song you listen to while watching the sunset and contemplating the peaks and valleys of life. It’s beautiful that way, and wait, did he just sing about reptile aliens cutting you open and pulling out your pain? Well, it’s in another dimension or galaxy, so at least there’s that.
6. “Scooter Blues” (2024)
There’s anthems, and then there are aspirational anthems. “Scooter Blues” is a goddamn perfect aspirational anthem. I mean, just look at the chorus lyrics, bub.
“Gonna hop in a boat and throw the paddle away/Offer my heart up to the break and the sway/Wake up every day in the sun/Kick off my flip-flops and go for a run”
Who among us hasn’t looked to do exactly that amidst some particularly trying times? Or just regular times when you need a break from the aforementioned times? I also think context plays a role in extolling this song’s greatness and appeal, as Passage du Desir came out in the summer of 2024, and I’m not sure if you follow the news at all, but that summer was especially uh…well, fucking weird and trying, mainly because of the Presidential election set to happen that fall. That feeling of weirdness and more continued for some time (kind of still happening, to be honest), and “Scooter Blues” helped keep things somewhat sane, offering up a lever to pull to escape the madness for a few minutes and dream of an alternate reality filled with islands, scooters, and most importantly, serenity.
5. “You Can Have the Crown” (2013)
SHIT. KICKING. COUNTRY.
It’s a thing, and it’s fantastic.
4. “Life of Sin” (2014)
If you break Simpson’s career into eras, then there’s the first era, which was more country and Americana. That one probably ended before A Sailor’s Guide to Earth, although the vibes carried over. Then there was the next era, which featured Simpson wandering the earth like the dude from Kung Fu, but instead of fighting crime, he was fighting the urge to do what was expected of him or what people thought he would. And then of course, there’s the current Johnny Blue Skies era. I can’t rank the eras. I love them all. But there is a purity to that first era, as Simpson felt loose and free, but also eager to make his mark. “Life of Sin” gets the country folks’ attention but also drops hints of the kind of message Simpson was interested in tackling: finding outlets amidst disparity. It’s also musically a blast, so you know, we love a twofer around here.
3. “If the Sun Never Rises Again” (2024)
Ol’ Sturg gets me thinking about my lady again on this tune, and that ain’t bad. But this is also another song about finding happiness and wondering how long that happiness can last. And I think that’s cool and interesting because we can all long for happiness, but we all also secretly hope it endures. Man, I remember back when I was in the dating scene and when starting to date someone, I would quickly think about how it would likely end badly. I mean, I can’t say I was in a great mental state at the time, but who is when out when riding the shit-ass emotional roller coaster that is dating. But whatever, you find the good times and hold onto the good times because things end. Or they don’t. This might end before or after we hit 4,000 words. Hard to know at this point, but we’ll see. Two songs left.
2. “Living the Dream” (2014)
Looking back at an artist’s catalog is fun because, with the benefit of hindsight, you can get hip to those breadcrumbs that lead from one album to another, breadcrumbs that might not have been visible at the time. Musically, “Living the Dream” feels like a precursor to the sound and feeling of A Sailor’s Guide to Earth. Lyrically, it falls along the same path, but I just think it’s interesting how the sound hints at the future. “Living the Dream” is also another one of those Simpson tunes that has a hypnotic quality to it, as you find yourself transfixed by the lyrics and then drifting off, thinking about what they mean and how on the money they are. It’s like jazz or Eminem’s music in that it’s hard to do anything else when listening to it because you can’t think of anything else.
1. “Keep It Between the Lines” (2016)
“Keep It Between the Lines” is just such an incredible piece of music. There are the massive-sounding horns, the slide guitar, the thumping drums, and, of course, the lyrics, which are made up of one gem of super sound advice after another.
“Don’t let them try to upsell you / There’s a reason they make chocolate and vanilla, too / If there’s any doubt, then there is no doubt / The gut don’t never lie / And the only word you’ll ever need to know in life is “why” / Keep your head out of the clouds / And remember to be kind / And just stay in school / Stay off the drugs and keep between the lines”
Oh, and you get the backup singers singing “Don’t sweat the small stuff” as the song rambles its way to its conclusion. It’s Americana doused with Motown/Staxish R&B and sprinkled with some Muscle Shoals goodness, and ultimately, it’s Sturgill effin’ Simpson doing whatever the hell he wants. A Sailor’s Guide to Earth isn’t just his best album, but a true introduction to his genius, and “Keep It Between the Lines” is that album’s high-water mark.
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