Lainey Wilson will be in discussion, with a performace to follow, at the GRAMMY Museum on Sept. 5. Learn more about the event here.

If there's one word to describe Lainey Wilson's life in the past year, it's whirlwind — which is exactly how she chose the name of her third album.

Since releasing Bell Bottom Country in 2022, the Louisiana-bred singer has been on an unprecedented tear. Whether she's selling out arenas nationwide, collecting countless awards, or launching or own line with Wrangler, Wilson is country music's newest queen. 

It's the culmination of a long and hard-fought journey for Wilson, who first moved to Nashville over a decade ago with not much more than a dream. But as she explained to GRAMMY.com earlier this year, Wilson has been manifesting this level of country music success since she wrote her first song at just 9 years old. 

"I've dedicated my life to it," she said. "And it really is cool to just feel like that little 9-year-old girl who was writing her first song, that she wasn't completely crazy."

Read More: Lainey Wilson On How Her Stardom Is A Testament To "Believin' And Receivin'"

Wilson grinded behind the scenes in songwriter rooms and at local gigs during her early years in Nashville, independently releasing her self-titled debut record in 2014, followed by the fittingly titled Tougher in 2016. It was a time of trial by fire as Wilson was learning how to navigate not only Nashville's music scene, but honing her own voice as a songwriter as well.

"Each album has been a reflection of the season I was in at the time,"  Wilson tells GRAMMY.com now. "My first album was the safest. I was young and had just moved to Nashville, but still hadn't seen too much of the world just yet. My next album became more confident and a little sassy. After that, I started to really discover my north star, staying open to all kinds of people and opportunities and sticking with the parts that felt the most authentic to me."

Just months before signing with Broken Bow Records in 2018, she delivered another self-titled project – this time, an EP, which conveyed both gratitude and sensitivity with songs like "Dreamcatcher" and "Breakin' Your Heart." Both qualities would soon become Wilson's trademark, and what particularly made listeners gravitate toward her breakthrough hit (and eventual first No. 1 at country radio), "Things A Man Oughta Know."

First appearing on her 2019 EP, Redneck Hollywood, "Things" was the second single on her debut studio album, 2021's Sayin' What I'm Thinkin'. Along with putting Wilson on the map, the LP also introduced fans to her unique style that she calls "bell bottom country" — sonically, a mix of nostalgic and twangy, pop-tinged sounds that never takes itself too seriously; visually, presented with flair (and flare) in her now-signature bell bottom pants.

"It's finding that thing that makes you unique, and leaning into it," Wilson told Rolling Stone in 2021. "It could be your story, your sound, where you're from, how you're raised, how you dress. I kept thinking about those words, 'bell-bottom country'…how can we do this? I definitely wanted a bit of Bobbie Gentry vibe, but also the pureness of Lee Ann Womack but also the sassiness of Dolly Parton. I wanted it to feel timeless and classic and, honestly, a little not too perfect."

Once "Things A Man Oughta Know" topped the charts, it wasn't long before Wilson did it again with Cole Swindell on "Never Say Never," her first of several chart-topping duets to come. She also hit the road opening for Jason Aldean, setting her up as an artist to watch and ensuring that she wouldn't be a flash-in-the-pan success story.  

After being unapologetically herself on Sayin' What I'm Thinkin', Wilson doubled down on that sentiment — and her brand — with Bell Bottom Country, a 16-song exploration of classic country instrumentation with glimmering '70s rock elements. It saw Wilson tell her story more than ever before, from the heartfelt ode to her father, "Those Boots (Deddy's Song)," to the strong-willed generational tale of "Wildflowers & Wild Horses." 

Though Bell Bottom Country was a bit of a slow burn — peaking at No. 9 on Billboard's Top Country Albums chart — Wilson's place in the country music zeitgeist was rapidly rising. Two weeks after Bell Bottom Country arrived, she made her acting debut as a guest star in "Yellowstone"; a month later, her booty-hugging bell bottoms went viral on TikTok.

Within the next several months, Bell Bottom Country spawned two No. 1 hits: the dynamic resilience tale, "Heart Like a Truck," and the "Strawberry Wine"-esque "Watermelon Moonshine." By the end of 2023, she'd score four No. 1s (thanks to collabs with HARDY and Jelly Roll), serve as direct support for Luke Combs' stadium tour, and become a brand ambassador for Wrangler jeans and Stella Rosa wines — all of it propelling Wilson to becoming a household name. And by May 2024, she'd scooped up three of the most coveted country awards: Entertainer Of The Year at both the Country Music Association Awards and the Academy Of Country Music Awards, and a GRAMMY for Best Country Album for Bell Bottom Country.

As her fame rose, Wilson had to make a conscious effort to stay grounded — especially because her personal life presented a whirlwind of its own. While the singer's career, as she puts it, "had me feeling like I was holding on to the tail of an airplane," her dad experienced several health issues, and simultaneously, she was balancing a relationship with former NFL quarterback Devlin Hodges.

"I had to learn how to rise to the occasion, deal with the pressure, and tend to my feelings and personal life around it all," Wilson explains. "I didn't feel in control of anything; like I was the victim of the chaos."

But as she started to make peace with her new reality, Wilson found solace in music. Soon, she had the makings of her fifth album, Whirlwind. "I [found] my footing through writing these songs and committing to a few good habits that have helped me become my best self," she adds.

Like Bell Bottom Country, Whirlwind sees Wilson telling her story — so, naturally, this time, there's a lot more love songs. "Counting Chickens" and "4x4xU" hint that she's found her life partner, while "Hang Tight Honey" and "Good Horses" remind that she won't let fame get in the way of a good thing. (Even the title track flips the proverbial whirlwind of her career into a metaphor for love: "We're a whirlwind/ But baby, loving you's a breeze.")

Whirlwind largely expands on Wilson's signature country flair, but a standout is the hip-hop, rock and country mash-up "Ring Finger" (which, ironically, is a breakup song; "I got the ring, he got the finger," she sings on the chorus). Much like with her previous two albums, Wilson teamed up with producer Jay Joyce for the project, noting that his willingness to experiment has helped her establish a sound that's fresh and unique, but also classic and timeless — a formula that's only proving to be more and more successful for the singer.

"I've become more confident, first and foremost," Wilson says of her growth. "I've seen beautiful things that come from pressure, and the things it can break. From that, I feel like I am writing with more wisdom and understanding and doing so in a way that kind of observes feelings instead of getting lost in them."

That wisdom and understanding is perhaps most apparent on "Middle Of It," an autobiographical illustration of how she's navigated her growing success. But whether she's exploring new sounds or new storylines, Wilson continues to prove that she'll never lose sight of the country-loving, hard-working girl she's always been.

Whirlwind paints a picture of Wilson rising above her success and its ensuing chaos, ultimately finding herself more at ease than ever before. It's all proof that her long-traveled journey has been well worth it — she's helped make country music cool again, and she doesn't plan on slowing down anytime soon.

Post Malone is getting ready to make perhaps the biggest pivot in a career full of them: a country album. Titled F-1 Trillion, it might seem like a strange move for a man who first came to fans' attention rap-singing over trap beats. His breakout track, after all, was co-produced by a guy best known for working with Tyga, Travis Porter and 2 Chainz.

But Post has never been comfortable sitting still. Over the years, the 10-time GRAMMY nominee has explored a great deal of musical ground, all the while branching out from the trap-influenced sound that first brought him fame in 2015. 

While he has broadened his vision both in terms of musical styles and subject matter, Post has long featured roots music elements in his sound. His country music turn shouldn't come as too much of a surprise to veteran listeners, who surely remember the Texas-raised star referencing George Strait's "All My Ex's Live In Texas" back on his first album.

In fact, Post and country music have a long-standing connection, from covers of genre classics to a Joe Diffie tribute at the 2023 CMA Awards. And with F-1 Trillion already spawning the biggest country hit of the year so far — the chart-topping Morgan Wallen collab "I Had Some Help" — Post's country venture is shaping up to be his latest massive success. 

He further proved that less than 48 hours before F-1 Trillion's Aug. 16 release, when he made his debut at country music's hallowed Grand Ole Opry. Three-time GRAMMY winner Brad Paisley may have put it best as he introduced Post onto the Opry stage: "This is a guy who made his mark in other formats, and has a country heart."

As Post releases F-1 Trillion, GRAMMY.com traces his musical history, from his hip-hop beginnings to his honky-tonk present. Below, see how Post Malone's style has evolved through the years.

Post's debut album, Stoney, and the pre-album mixtape teaser, August 26th, both feel like an expansion of his breakout hit "White Iverson." Like that smash single, most of the tracks on these two projects feature trap-style drums, with their distinctive 808-style kick drums and fast hi-hats. Post is sing-rapping, often about topics that wouldn't sound out of place on any other circa-2016 trap project: luxury brands, jewelry, being at the strip club, and flexing on haters.

But there was something else there, too. Post had his emotional moments, where his still-new success was giving him the blues. There was also rock influence — "Hollywood Dreams" even rewrites a Fleetwood Mac classic. And both projects had moments of roots music, as well as blues and folk overtones that would only grow more prominent as time went on. August 26th's "Oh God," which closes the project, is basically a blues number, as its prominent acoustic guitar and lyrics with ominous Biblical references testify. Stoney likewise closes with an acoustic song, "Feeling Whitney" — leaving his newfound mass audience convinced that he knew how to handle a stripped-down ballad.

Post's second proper album has two main kinds of songs, both of which are reflections on his recent success. There are the songs about the spoils of stardom (parties, drugs, women, money, luxury goods, and especially cars — the album ends with three automotive tracks in a row); and then there are the songs about its downsides, often with very literal titles like "Paranoid" and "Rich & Sad."

Musically, Stoney's trap drums are still there. But Post's melodic taste has expanded, from standard rap-singing to something a little closer to the rock and roll he loves (this is, after all, a guy who will cover an hour's worth of Nirvana songs at the drop of a hat). 

The outlier on this album is "Stay," an acoustic-heavy pop song so Beatles-esque that its working title was "George," for George Harrison. Like "Feeling Whitney," "Stay" further shows Post's affinity for quieter, more stripped-down songs — an ability he'd continue to refine with subsequent albums, including F-1 Trillion's heartfelt ode to his daughter, "Yours."

With 2019's Hollywood's Bleeding, Post dares to leave the trap drums and hip-hop stylings alone for multiple songs at a time. The album does bring in its fair share of rappers to be sure; DaBaby, Future, Young Thug, Swae Lee, and Travis Scott all feature. But the main thing that sets the project apart from its predecessors is not that, nor the subject matter, but the variety.

There is one song that veers close to heavy metal, "Take What You Want," which was produced by classic rock whisperer Andrew Watt and featured the Prince of Darkness, Ozzy Osbourne. There's a sunny jam band-style track about life on the road ("Myself"). There's an indie-pop number ("Circles"). There's one straight-ahead pop song ("Staring At The Sun"), and a different one with a string section ("Internet"). There are several rockers that could (and did) fit right in on alternative radio.

Hollywood Bleeding was the first time that Post leaned all the way into his versatility. He fully inhabits each genre he tries, exploring almost every nook and cranny of the contemporary rock and pop world along the way. After such a varied album, it only makes sense that his next project should be more focused. In retrospect, this album can be read as an early indication that a country album was all but inevitable: if Post can convincingly pull off so many genres, why not country?

Malone's first album of the pandemic era continues his evolution away from hip-hop trappings begun on its predecessor, and is more cohesive sonically than its predecessor. Even the songs with actual rapping, like a collaboration with Doja Cat, sound more like pop than rap.

Instead, Twelve Carat Toothache is the work of a musician who wants to leave the hip-hop trappings of the likes of "White Iverson" and "Go Flex" — musical and lyrical both — behind him. The project begins with just acoustic piano and Post's voice on "Reputation," and ends with a voice-and-acoustic-guitar demo of album standout "Euthanasia" (titled "New Recording 12, Jan 3, 2020"). 

Twelve Carat Toothache has plenty of ballads: acoustic ones, rap-singing ones, dramatic rock ones. And big emotions are the name of the game — tracks subtitled "A Happier Song" and "A Sadder Song" are back-to-back, and "Euthanasia" and "When I'm Alone" are as feelings-forward as their titles would indicate. 

After the exploration and variety of Hollywood's Bleeding, Twelve Carat Toothache indicates that Post wants to be taken seriously as an album artist — and, as F-1 Trillion's down-home songs would later fully reveal, someone who can tug on the listener's heartstrings. He would continue those quests in a most unexpected way: by looking back to the '80s.

We're a long way from rap now; AUSTIN is fully a rock and pop album. There are no rapper guest appearances — in fact, there are no guest appearances at all. And with his birth name serving as the album's title, it seems that was every bit intentional.

The record has plenty of rootsy, acoustic songs, especially towards the end. But it also has something different for Post: a new wave, 1980s synth-pop feel on a number of tracks. The cohesiveness of Twelve Carat Toothache is retained, and the end product is extremely professional and polished. As a whole, the album (perhaps uncoincidentally) puts Post's songwriting skills on full display. 

At this point, Post has traveled very far from his early days. His next move would have to be something that builds on his now-well-established cred in pop and rock styles, but that would also surprise his current fans — and maybe bring him some new ones. 

Rumors began over a year ago that Post was going to release a country album, and he openly acknowledged it was a possibility in interviews. So it was no surprise when F-1 Trillion was finally announced earlier this year.

As the project's lead single hints, Malone will have plenty of help: F-1 Trillion will feature guest appearances from country titans Morgan Wallen, Blake Shelton, Brad Paisley, Luke Combs, Chris Stapleton, Tim McGraw, Lainey Wilson, Jelly Roll, Hank Williams, Jr., Dolly Parton and more. The who's-who-of-country guest list shows that Post has plenty of clout in Nashville — and considering the album reportedly moved more than 500,000 units before it was even released on Aug. 16, he's making waves with country fans, too.

The songs vary sonically from big country-pop hooks ("I Had Some Help") to fiddle-filled romps ("Pour Me A Drink") to tear-jerking ballads that are sure to make their way into the repertoire of wedding bands across the country ("Yours"). Post blends in with his vocal costars, with a little bit of AutoTune on a few tracks marking the only noticeable connection to his trap music beginnings.

Lyrically, he puts plenty of emphasis on clear narrative and the puns and reversals that are country music's stock in trade (in the Combs duet "Guy For That," he has a "guy" on speed dial for every possible need — except, of course, for repairing his girl's broken heart). Now, he's focused on telling a straightforward, compelling story versus evoking mood and emotion — an indication that nearly a decade in, he's still growing as a songwriter.

The fact that Post can convincingly pull off a country album continues to demonstrate to the world that he's as unpredictable as he's always been. There's no telling where he'll end up next, and that's what makes him so intriguing to his fans — a group that now includes people who love both "White Iverson" and "White Horse."

Just hours before Ella Langley released her debut album, hungover, she checked off another career goal: playing a stadium. Opening for Morgan Wallen in Kansas City, Missouri, she couldn't help but flash back to young Ella, whose musical aspirations have long been stadium-sized.

"I've been manifesting this my whole life. People used to ask me, 'How far do you want to take it?' and I was like, 'As far as I can — which is, in my brain, a stadium,'" the rising country star tells GRAMMY.com on the day of her album release. "So with the record coming out and playing my first stadium, I just kept thinking about that little girl that would lay in her room, stare at the ceiling and wonder if her dream would ever work out. And yesterday, it felt like it's coming true."

It's not entirely surprising that two major milestones happened simultaneously for the Hope Hull, Alabama native. Since she moved to Nashville in 2019, Langley has been winning over peers and fans alike with her candid storytelling and playful demeanor. It's exactly why she's been touted as an artist to watch by CMT and the Grand Ole Opry, among many others; it's also why her most recent single, the cheeky Riley Green team-up "you look like you love me," has been making waves on social media and even across the pond in the U.K., where it's already hit No. 1.

The rest of hungover further showcases her raw-and-real approach, from the twangy kiss-off "cowboy friends" to the regretful tale of "love you tonight." She masterfully finds a balance between straightforward and meaningful, ultimately reminding listeners that it's okay to not be perfect — and to lean into that.

"There's this level of honest that I'm not afraid to be," Langley says. "I think people need somebody like that."

Below, the buzzy country singer details the "badass" women who have inspired her strong-willed attitude, how she's seen her music impact fans, and why she'll never stop thinking of her growing success as "just nuts."

You've said you didn't really consider yourself a songwriter, which is why you moved to Nashville. Now you've co-written two full projects. Clearly you had some sort of songwriting talent in you!

I just have the imagination of a 10-year-old, and that helps, for sure, with songwriting. My dad's an incredible storyteller. My grandpa was an incredible storyteller. Really, storytelling is what my family did. If you come and sit at our dinner table, everyone's talking over each other, laughing loud, telling the same stories that everyone's heard. If one new person sits at the kitchen table, they're in for a loud dinner.

I was singing constantly as a kid. Like I said, I've known my whole life what I wanted to do, so I was always doing it. But I tried to sit down and write songs, and every time I would try to write a whole song, it came out weird. Melodies are always what I would write a lot of, I still feel like [that's] one of my strong suits is in a room.

COVID hit six months after I moved to town, and that was a blessing in disguise for me. I was playing shows still back in Alabama and all over the Southeast. That's how I was paying my bills. I was playing cover gigs — this only job I've ever had, minus a stint in high school with a trampoline park. But that didn't last too long. [Laughs.]

When I [first] moved, I was struggling figuring out how to write. But then COVID hit, and I couldn't do anything but write songs. I found some incredible people in that six months I had before [the pandemic], and that's all I did was write, write, write. 

What was the first song that you wrote that you were like, This is who I want to be as an artist?

I don't think there was one song that did that for me. I was talking to Lainey Wilson last night about how it's really crazy [that] when you move to town, people are like, "Who are you as an artist?" You ask a 20-year-old who they are — I don't know! I don't know anything! I'm just doing my best. I'm just trying to survive without my parents telling me what to do right now. So really, this record is my life that I've written from 20 to 25. They're all just journal entries. 

We cut "paint in town blue," "hungover," "you look like you love me," and "nicotine" all this month last year, and I still had no idea what the title was going to be. When I was driving around listening to the mixes, I was listening to "hungover." When I was thinking about the title hungover, and what that represents, I was like, Oh, my God, it just does represent everyone's life from 18 to 25. It's growing up, and just kind of giving yourself grace to live your life and figure that out.

Since you've been manifesting this for your whole life, did you have a vision of what you were wanting to bring to country music?

No. Putting this record together has made it make sense. You know, you go so long [playing] cover gigs, and then [when] I started doing my first tour, I'm singing a 45-minute set and I have one song out.

It took this record, putting this together, and kind of figuring that out to really understand who I want to be for my fans — and actually realizing that I have fans now, which is crazy to think and say. Every show I see more and more people singing, and it's as many girls as it is guys singing the same songs. And I love that they're just singing their hearts out.

I think what I want to be for my fans and for country music is just — grace is my word. You don't always have to be perfect. None of us are. So just do your best and love what you do.

The titles of both of the projects you've put out, your EP Excuse The Mess and now hungover, are so indicative of that. Have you had a chance to go back to Excuse The Mess and compare the two, or think about how much you've grown?

Definitely. I thought a lot about Excuse The Mess when I was building this record. I'm so proud of that little project and what came out of it. I got nominated for my first award ever off that record. And the two acoustic songs at the end of it are still two of my favorite songs I've ever written. 

I think Excuse The Mess to hungover is a good jump. It's almost like an extension of that. But like I said, my songs are journal entries of my life. [For] the next one, hopefully I won't do as many crazy ass things. [Laughs.]

But that's what makes you relatable and so lovable — you're just singing about the stuff that mid 20-somethings do. You make the mistakes you learn from them, and you sing about them, and everybody loves it. We've all been there!

Exactly. It's funny, I started realizing pretty early on in town how honest I was in [songwriting sessions]. Because a lot of writers were like, "Dang!" I always say that the songwriters in Nashville know way too much about my personal life. 

I played a show when I was on tour with Riley [Green] earlier this year. We played in Huntsville, Alabama, and this was the first time I've played a show in Alabama in a minute. We did a meet and greet, and so many people [I know] came. My little sister's going into her senior year [of high school]...she came up to me and she was like, "Watching you do what you do — just the fact that you moved, and watching you just keep pushing at it, I can get up and go to the gym. I can get up and clean my house. You don't understand the hope and motivation that it gives people like us."

That was kind of a big moment for me. This is affecting people now. It's just nuts.

See, you can keep doing crazy s— and you'll still have fans!

I've been this way since the day I was born, so I figure it's not going to stop now. My frontal cortex did develop, so maybe I'll think a little bit more.

I had a feeling you've always been a straight shooter.

It's kind of funny — I think it's something that, if somebody's new [on my team], they have to get used to. If you're used to it, it's kind of nice. I say exactly what I mean all the time. I never beat around the bush!

Where do you think you got that from?

My dad. He's honest — and my mom's honest, but they're very honest in different ways. My dad's a little more Southern Baptist where he's, like, around some people, gonna be a little sweeter. That does rub off on me, because I'm from the South. But, I don't know, I've just always said exactly what I think. Sometimes it's good and sometimes it's not. But the older I get, the more I realize it pays off! 

It's made me some really cool relationships in this job, with other artists and just people in general. I met Eric Church for the first time the other night. In Nashville, there's this unspoken rule about how you treat artists — especially when you're another artist, you don't want to just walk up and be weird. But I did the Toby Keith tribute [in Nashville on July 29], and whenever I heard Eric Church was playing it [too], I couldn't stop thinking, Am I going to get a chance to shake this man's hand? He's such a legend to me. 

There was a bar side stage, and he was standing at the end of the bar, right next to Lainey [Wilson] and HARDY and I'm like, Oh my God, that's perfect. I'm friends with them, this is my in! I walked up there and I was like, "I'm not trying to be weird, and if I am, please just tell me. But I have to tell you, I just think you're a badass, and I would kick myself in the ass if I did not shake your hand and tell you that." And that's how I got a tour with Jamey Johnson — I said the exact same thing. 

It's like, how are you surrounded by these people that you've grown up watching, wanting to do what they do, admiring, learning from, and then you just get to meet them, and they're all "Love your voice, love your songs!" Like, "You know who I am? Wow, I'm gonna need to sit down."

So that's how Eric responded?

Yes! It was nuts! Then I leaned into HARDY and I said, "Do you remember the first time you were around the most famous people you've ever been around?" He said, "Yeah, is that you right now?" I said, "Yeah." He was like, "That's awesome!" He had the biggest grin on his face.

It's cool, because Eric is a straight shooter too, so I'm sure he loves seeing another female artist doing that. Because since, like, Miranda Lambert, there really hasn't been a female country artist with such a power stance like, "No, I'm not dealing with your BS."

That's why I think "you look like you love me" is such a cool song, because it is really about women empowerment. My mom's a strong ass female. My grandma was that way. A lot of women in my life are just badasses, and I've seen them go through a lot of s—. I grew up watching them stand up for themselves. 

And the older you get, I guess, the more feminine rage you get. I don't know if that's how it usually goes, but for me personally, yes. You know, like "cowboy friends" — you can do whatever you want. Why does it have to be the guy? We know we want more than men, always! Unless you ask me where I want to eat, I always know what I want! 

So, go walk up to him! Even if it doesn't work out, whatever. One time I did that at the gym and it didn't work out. My photographer watched me do it. It was terrible.

Something tells me that man regrets turning you down.

He had a girlfriend. Or maybe he didn't and he just said that. [Laughs.] Sometimes you just have to laugh at yourself. It's fine — you don't always have to be cool, you know?

Has anyone ever shut you down for being so honest, especially as a female artist?

No, I think it surprises 'em more than anything.

I've been on tour with a lot of outlaws. I started out with Randy Houser, then I went on a Koe Wetzel, and then we did Jamey Johnson, and then Cody Johnson, and now we've got Riley [Green] and HARDY and Morgan [Wallen]. And that's a bunch of outlaws, if you ask me. So you kind of do have to be a badass female around here, you know? 

I'm here to play. I'm here to show everybody what I've been working so hard on, and what my band and my team have been working hard on. And I think they respect that. They respect the honesty and the grind that I have. Real sees real, and I think that's what's happening.

Now that you've checked off the debut album, what else are you working on manifesting?

So many things. I have so many plans. I've always been like this. I have so many things spinning in my brain. I'm already working on the title for the next record. The record's out, so now it's time for the next thing. Everyone can listen to this while I'm working on that!

So you're a big manifester?

Oh, constantly. I write in my journal, I make manifestation boards. Every New Year's for the past two or three years, me and a bunch of my team get together, and we have a big arts and crafts party. We play music and manifest. It's crazy to see the things that I put on my board last year that are coming true this year.

What are some of those things?

[Performing at] Red Rocks, the album coming out, getting on a bus. I made friends with Miranda Lambert this year. She's been on my manifestation board three years in a row, so that was cool.

I think I put a gold record on there, which happened this year. Me and Caylee — my photographer who also helps run my social media — we had a goal for how many followers we wanted to get to, and we've already beat that. It's just nuts to see the things that you really hope for come true.

It's hard to imagine country music without Alan Jackson. One of the trailblazers who helped define an entire generation of country music, his accolades include 26 No. 1s on country radio, over 75 million records sold worldwide, two GRAMMYs, and inductions into both the Grand Ole Opry and the Country Music Hall of Fame.

It's been a remarkable run for the Newnan, Georgia native that first moved to Nashville in the mid-80's to chase his musical dreams. He'd eventually land a job in The Nashville Network's mailroom and get put into contact with Glen Campbell, whom his wife met while working as a flight attendant. With the "Rhinestone Cowboy" in his corner, Jackson soon signed his first record deal with Arista Nashville in 1989 and released his debut record, Here In The Real World, the following year, and the rest is history.

In the 20 albums that have followed, Jackson has staked his claim as not just one of the best country artists of the 90's and 2000's, but one of the greatest of all time. While the numbers are certainly in his favor, the most undeniable variable in the equation is how adored he is by fans. That love and appreciation will be on full display during Jackson's "Last Call: One More For The Road Tour," which kicked off Aug. 2 at Boston's TD Garden and wraps up May 17, 2025 at Milwaukee's Fiserv Forum.

To commemorate Jackson's legacy and celebrate his final act, here are a dozen bangers from the two-time GRAMMY winner that helped cement his Hall of Fame status.

Music City is filled with folks who want to make it big in the music business, grinding it out on Broadway and around town in hopes of catching their big break. Jackson explores that concept with "Chasin' That Neon Rainbow," detailing his own journey from playing Georgia's honky tonk circuit to heading to Nashville's Music Row to live out his lifelong dream — because, as he says in the chorus, "all I've ever wanted is to pick this guitar and sing."

Though Jackson's next single, "I'd Love You All Over Again," marked his first No. 1, "Chasin' That Neon Rainbow" reached No. 2 and helped introduce his signature twangy, yet soulful sound. Along with being a fan favorite, the song has clearly remained important to Jackson, too, as it's still a set staple to this day.

While Jackson isn't necessarily known for writing tear-in-your-beer tunes, he can still do it with the best of them. Take "Don't Rock The Jukebox," a story about a down-on-his-luck bar patron longing for some country music to ail his heartbreak.

As such, throughout the song he can be heard pleading to other barflys to not put on any rock music because "I wanna hear some Jones/ 'Cause my heart ain't ready/ For the Rolling Stones." It's a story most of us have seen play out a time or two ourselves, and the homage to George Jones — one of the best penners of tear-in-your-beer songs — is a nice touch.

The country hit of the summer in 1993, "Chattahoochee" tells the tale of having fun and growing up near the river of the same name straddling the Georgia-Florida-Alabama border. While the song delves into Jackson's own experiences growing up there, it's also ambiguous enough to fit with anyone coming from small town America, or at least anywhere that "It gets hotter than a hoochie coochie."

Despite Jackson initially thinking it wouldn't be a hit, "Chattahoochee" quickly transformed into one of his biggest songs, the reverberations of which are still being felt today. In the 30 years since, ditties about lighthearted summer fun on the water have become as central to country songwriting as pickup trucks, cheap beer and heartbreak, and "Chattahoochee" was one of the first to kickstart that trend.

Jackson's 40+ year marriage to his wife, Denise, has long served as inspiration for his music, and their relationship takes center stage on "Livin' On Love." The sentimental song sees the singer looking back on their time spent together, from their humble beginnings before he broke through in music ("Two young people without a thing") to raising a family and still being just as crazy about each other through it all.

While the retrospective tune illustrates Jackson's endearing love for his wife that "can walk through a fire without blinkin'," its message is one that hits home with lovebirds everywhere — no doubt a big reason the song eventually became his ninth No. 1 hit.

The most revered track from Jackson's stacked 1994 album Who I Am, "Gone Country" serves as a commentary of the country music industry, which was in its '90s heyday at the time of the song's release. While it's meant in part as a jab at those in the business who value money over artistic integrity, the tune is also intended as a celebration of the success of country music in the '90s, and how the music business was adapting to capitalize on the craze. ("Yeah, we've gone county/ The whole world's gone country," he sings on the final verses.)

The song has come full circle as of late, given the current moment country music is having in pop culture — from the success of stars like Morgan Wallen and Zach Bryan to crossover records from Beyoncé, Post Malone and others. Not only has that proven the song to be just as relevant 30 years later, but it also shows just how spot-on Jackson's postulating was.

Sometimes life's best gifts come in the smallest of packages. This is evidenced by Jackson's "Little Bitty," a little ditty from 1996's Everything I Love that became the Georgian's 14th No. 1 hit.

Aside from its quirky, lighthearted narrative about finding the joys in life's small and mundane moments, the song also contains an underlying message of having a positive mindset and not letting every little transgression get you down. Its exquisite word play and universal message is just as powerful now as it was when Jackson first recorded it — yet another example of how Jackson's songwriting resonates with listeners past, present and future.

"Where I Come From," 'When Somebody Loves You' (2000)

The third single from 2000's When Somebody Loves You, "Where I Come From" details a long-haul truck driver's various encounters on the road. Whether it's a cop in New Jersey questioning his accent or a barbecue dinner in Detroit that isn't anything like what his mother would make, the song is a metaphorical pondering of the ways Jackson's Southern upbringing varies from the places he passes through.

Each story grows goofier than the last, illustrating Jackon's penchant for simple yet captivating storytelling. And while "Where I Come From" is ultimately rooted in his Southern culture, his passionate delivery on the anthemic chorus makes anyone want to sing along, no matter where you're from.

While countless songs have been written about the September 11, 2001 attacks, it's hard to find one with more apolitical grace or as much empathy as Alan Jackson on "Where Were You (When The World Stopped Turning)." 

Rather than containing vengeful imagery of boots kicking butts, the song instead details Jackson's own experiences and mixed emotions of the day — from shouting in anger to sitting down to cry — to create arguably his most powerful and unifying piece of work. And its moving message resonated with country fans, earning Jackson his 19th No. 1.

Written in remembrance of his late father Eugene, "Drive (For Daddy Gene") sees Jackson recalling memories with his dad — particularly, how he'd let him drive around the countryside near their home in the beat up truck they worked on together.

As the emotions and memories keep flooding back, Jackson eventually reflects on how he's already begun to make similar memories with his daughters. Altogether, the stories make for one of Jackson's most poignant songs that — combined with the single that preceded it, "Where Were You (When The World Stopped Turning)" — show how he strikes a chord with listeners on somber songs just as much as his upbeat country anthems.

Despite delivering a couple of his most poignant hits on 2002's Drive, Jackson delivered his most heartfelt love letter to date with 2003's "Remember When." Much like "Livin' On Love," the song looks back on his marriage and how the bond with his wife has only strengthened over time.

One of two new tracks featured on Jackson's second greatest hits collection, "Remember When" is a stark contrast from the classic drinking song "It's Five O'Clock Somewhere" featuring Jimmy Buffett. But while the latter became Jackson's biggest crossover hit, "Remember When" remains the country legend's only single to be certified four-times platinum by the RIAA (as of press time) — further proof that Jackson made an impact with his music no matter the subject.

"Freight Train," 'Freight Train' (2010)

The title track from Jackson's 16th studio record, "Freight Train" visualizes the singer as a steam locomotive running down the tracks away from the woman that scorned him. On it, he's left to untangle himself from the twisted emotions that had kept him from leaving her sooner: "Well every time I talk to you I hear your jealous lines/ I feel like I've been left abandoned on some old railway side."

Even nearly 20 albums into his career, Jackson was still delivering stories that listeners hadn't heard from him before — and "Freight Train" is a prime example of how Jackson has long been able to keep listeners on their toes.

Though Jackson is known as one of the world's most accomplished country musicians, he has also forayed into gospel and bluegrass within his mammoth 21-album collection. "Long Hard Road" — a deep cut from his simply titled 2013 effort, The Bluegrass Album — is a perfect example of the latter, as Jackson sings of a rugged journey that's changed him "for good and some for bad" and made him long for a way back home.

The song's hard-driving soundscapes and bold group harmonies make it a natural fit in the bluegrass space. At the same time, it maintains the integrity and distinct voice that's made Jackson him such a beloved star — one whose legacy will live on long after his farewell tour concludes.

Orville Peck wants to make one thing clear: he doesn't miss the tassels on his mask.

"The fringe was sort of a pain in the ass for a lot of things, like going to dinners and things like that. So now that's a lot easier," the country crooner tells GRAMMY.com with a laugh. "When I first started doing shows with my new mask, it was a little nerve-wracking to go out and feel like I was sort of a little naked, but I've gotten over that now."

Tassels or not, Peck's signature face covering has been a major part of his mystique since he burst onto the country scene with his 2019 debut album, Pony. Part Lone Ranger symbol, part leather daddy roleplay, the mask has both protected the singer's true identity (sure, that information is out there, but we're not about to spoil it here) and added a theatrical allure to the brand of offbeat outlaw country that's made him famous.

But on the verge of releasing Stampede, his new duets album (which dropped Aug. 2 via Warner Records), Peck felt confident it was time to update his look — fringe be damned. "I know people feel very connected to the mask and very protective over it, but I make art for myself," he says just days after playing the Newport Folk Festival as part of his ongoing Stampede Tour, which wraps with two shows in Brooklyn, New York on Oct. 19 and 20.

"So when I know it's time to evolve and change something, that's because I need a challenge," the singer continues. "Something different to keep me inspired as an artist and making good art, rather than just doing the same thing over and over again, or pandering to people who expect me to be something or someone."

From the moment he first donned the fringed mask and introduced the world to his stage name, Peck has been hell-bent on blazing his own path through the country scene. After all, he's never checked all — or any — of the boxes the Nashville elite might expect. Born in Johannesburg, South Africa and raised in Vancouver, Canada, the deep-voiced troubadour also happens to be one of the few proudly and openly gay men in the country space — all markers that buck traditional conventions of what makes a 21st century country star.

"I say I'm from all over the place, which is essentially the truth," the singer explained in the 2020 mini-documentary exploring his origins titled "The Orville Peck Story." "You know, I've kind of been on the road my whole life. I was a huge fan of Westerns, I was a huge fan of the Lone Ranger. Looking back on it, being this out-of-place, lonely kid, I can really understand why the image of a cowboy connected to me so hard."

The archetype also runs in his bloodline: in South Africa: his grandfather was a gun-toting sheriff on horseback, and a young Orville spent years roaming the bush with his dad, but the singer is quick to clarify with a knowing chuckle that he sees himself as "more the Marty Robbins [type] rather than the guy who's actually working the ranch."

Peck also admits he's felt, at times, excluded from what he calls the "Nashville machine" of major-label country ("I think they have a very decided mandate of what they want to be country music, and what they think is profitable — and sadly, that doesn't leave tons of room for diversity"). But his success as an outlier who's both queer and non-American is also a testament to the fact that the genre doesn't belong exclusively to some select group of elites dictating who's allowed to pick up a guitar. 

"As far as what makes a country musician, I think it's anybody who has a love for country and wants to have their perspective in it," he adds. "With all due, the most important and meaningful mechanism of country is, in fact, just storytelling."

If anything, Peck's first album harkened back to a time — and sound — that predates the glossy sheen and honky-tonk bro culture of modern country altogether. Early songs like "Hope to Die" and "Turn to Hate" tapped into the frank, hardscrabble narratives favored by greats like Johnny Cash, Loretta Lynn and Merle Haggard, as Peck painted vivid imagery on the self-produced Pony of a Wild West filled with heartbreak and hatred, ghost towns and standoffs with lost souls. ("Stark, hollow town, Carson City lights/ Baby, let's get high/ Spend a Johnny's cash, hitch another ride," he intones on "Dead of Night," the LP's haunting opener.)

Quick to strike while the proverbial cattle brand was hot, Peck soon inked a deal with Columbia Records and doubled down on the vintage aesthetic and high noon-ready sonic palette of Pony with the 2020 EP, Show Pony.

A more flamboyant evolution of its predecessor, the six-track project continued Peck's reverence for country icons of the past by featuring a menacing reinvention of Bobbie Gentry's '60s-era crossover hit "Fancy" on top of brooding originals like "Summertime" and "No Glory in the West." The biggest spectacle on Show Pony, however, came in the form of "Legends Never Die," an audacious, anthemic duet with none other than Shania Twain.

Not only did the song give the five-time GRAMMY winner an excuse to revisit her well-documented love for a leopard-print jumpsuit — it added a dash of glitz and glamor to Peck's mysterious persona, as he harmonized with the Queen of Country Pop on lines like, "I've been rode hard and put up wet/ Ain't nothing in this world that I can't get/ Don't worry 'bout making sure they won't forget/ No it's fine/ 'Cause legends never die."

At the time, working with his idol served as a major breakout moment for the musical desperado. But as the first duet of Peck's career — which now includes an album dedicated to the art of collaboration — the song was a marked departure from his tried and true approach as a musical Lone Ranger.

"I was willing to do it because it was Shania and I was so obsessed with her. You know, I wrote the song for her and I," he says. "But I used to be very opposed to even writing with other people. It was hard for me because I grew up so DIY in this industry, and so protective over my vision and my music that it was a skill I had to develop."

Throughout the next couple of years, Peck also had to learn how to manage the realities of his growing fame. The country crooner's career reached new heights with the release of his sophomore album, Bronco, which he rolled out in three chapters over the winter and spring of 2022. 

Steeped in the singer's now-signature pastiche of hypermasculine cowboy fantasies, the studio effort successfully balanced the camp of sly, homoerotic cuts like "Daytona Sand" and "The Curse of the Blackened Eye" with the yearning sincerity of ballads like "C'mon Baby, Cry" and "Hexie Mountains." Peck also searched out new sonic influences on the album, finding inspiration in everything from '60s and '70s psychedelia to South African folk music like marabi and mbaqanga — essentially paving the way for the genre-hopping sound of Stampede.

"With Pony, [that] was my first, lonely, frightened little album, and then Show Pony was my glitzy attempt at confidence, and now Bronco is all about breaking free and being untamed and unrestrained," Peck said in an interview with Billboard Pride at the time.

The muscled musical freedom he harnessed on his sophomore set paid off: in addition to becoming the singer's first official entry on the Billboard 200, it was a genre-hopping success on the folk, country and rock charts — where it reached Nos. 4, 11 and 13, respectively.

Bronco also arrived in the wake of a cavalcade of ever-increasingly high-profile opportunities for Peck: Lady Gaga tapped him to reimagine "Born This Way" for BORN THIS WAY THE TENTH ANNIVERSARY; Harry Styles asked the singer to open for his fan-favorite "Harryween" shows at Madison Square Garden; and he starred in the campaign for Beyoncé's Ivy Park Rodeo fashion line. 

And that's not all: country music's self-described anti-hero suddenly found himself labeled a gay icon-in-the-making as he appeared as a coach and celebrity mentor on the Apple TV+ series My Kind of Country, received the Cultural Icon Award by The Tom of Finland Foundation for "artistic achievement and immeasurable contributions to the art and culture of [the LGBTQIA+] community," and appeared as a guest judge on the main stage of RuPaul's Drag Race.

Read More: How Queer Country Artists Are Creating Space For Inclusive Stories In The Genre

Eager to get back on the road following the pandemic, Peck announced a sprawling tour in support of Bronco, which would take him all around the country through the summer of 2023. But following a sold-out show at The Theater at Madison Square Garden that June for Pride, the singer reached a breaking point.

"I was starting to work on a new album and was feeling a lot of pressure from the jump in success that I'd had around that time; it was all just coming to a head and I was completely burning myself out," he says. "So I had to basically make the decision to stop everything and go take care of myself, because my depression and my mental health was so bad. It was really just too much for me."

So, more than a year after Bronco's release, Peck stopped the avalanche of momentum and canceled the rest of The Bronco Tour to focus on his mental health. "It definitely wasn't easy," he says with hindsight. "I felt like I was letting myself down, everyone who works with me down…all my fans. So it was a very heavy and hard decision. But I'm so happy I did it because it saved my life."

Peck largely spent the rest of the year away from the spotlight, candidly acknowledging in a December Instagram post that "2023 unexpectedly turned out to be the hardest year of my life." But having taken the necessary time to heal, he was ready to dive into his next musical chapter, and within a matter of weeks, he was cryptically teasing Stampede.

Coming off of such a major reset, Peck explains that he views Stampede as a standalone "concept album" of sorts, rather than the latest entry in his canon of solo records. Instead of going it alone, he packed the album with a parade of close friends and music industry legends, both fellow rabble-rousers in the country scene and surprising GRAMMY winners from the worlds of dance-pop, American roots music, EDM and alt-rock.

The album's first single was a duet with Willie Nelson on "Cowboys Are Frequently Secretly Fond of Each Other" — a groundbreaking and subversive yarn written in 1981 by Latin country artist Ned Sublette that Nelson first recorded in 2006.

"I couldn't believe that Willie Nelson was singing a song about gay cowboys," Peck says of the first time he heard the country icon's solo version, which found the 12-time GRAMMY winner singing, "Cowboys are frequently secretly fond of each other/ Say, what do you think all them saddles and boots was about?" with a wink over waltzing guitar. 

It was Nelson's idea to update the song as a duet, which eventually led Peck to the idea of Stampede. In fact, he asked the younger singer to collaborate on the track the first time they ever met aboard the 91-year-old legend's famous tour bus. "It was overwhelming and validating," Peck remembers. "I mean, if we want to talk about feeling excluded from country, nothing makes you feel more included than Willie Nelson asking you to do a duet."

High off making magic with Nelson, Peck extended that same spirit of camaraderie to some of his closest friends and peers from all corners of the country landscape — from his My Kind of Country costar Mickey Guyton to neotraditional country trio Midland, as well as Canadian folk chanteuse Allison Russell and crosspicking bluegrass virtuoso Molly Tuttle, whom Peck touts as "one of the best guitarists alive."

The singer was equally intentional when it came to melding his sound with other genres, whether he was grooving to the chugging, celebratory "Death Valley High" with Beck, whipping up a whistling, disco-country bop in "Midnight Ride" with Kylie Minogue and Diplo or going toe to toe in a vocal showcase with Teddy Swims on the soaring, gospel-tinged "Ever You're Gone." Along with showing his versatility, Stampede also displays a rejuvenated Peck who is eager to continue pushing the boundaries of country music and beyond.

"I didn't intend for it to be in the usual vein of my solo stuff," Peck says of his approach to the album. "The intention was that I wanted to collaborate with each of these people. So take 50 percent of me and 50 percent of whoever the other artist is, and see what we could make together, you know?"

While Stampede kicks off on an unabashedly gay note with that Willie Nelson duet, it's bookended by a joyful cover of Glen Campbell's beloved 1975 classic "Rhinestone Cowboy." Peck assembled pals Waylon Payne, TJ Osborne of Brothers Osborne and Fancy Hagood for a "star-spangled rodeo" of a finale that felt poignantly momentous for all four trailblazers. 

"Obviously, there are not that many out gay men in country music, so we all kind of have this bond together," Peck points out, noting that the quartet have cleverly christened themselves "The High-Gay Men" in their ongoing group chat. "So I knew that it was important to do something really historic in a sense, and meaningful that four, out, proud, gay men in country could get together and do a song together."

Now that the album is out, Peck is prepared to keep the Stampede raging. His sixth annual Orville Peck's Rodeo — a roving mini-festival the singer first dreamt up in the days of Pony — will take place later this summer as part of his touring plans in support of the LP. Hosted by the legendary John Waters and co-headlined by Tanya Tucker, the event promises to deliver three days of live music, drag performances, after-parties and surprises galore. And for the first time, it's taking over Nashville. 

Triumphantly descending on Music City U.S.A. with a band of misfits and icons in tow might feel like nothing short of vindication for a masked vigilante who's spent his entire career playing by his own rules. But for Peck, it's always been about his dedication to the art rather than seeking approval from the industry that surrounds it. 

"I'll say it like this: I don't feel like an outsider in country music," he concludes. "Because I love country music more than anybody."