Today, the newly revamped and renamed TrailBlazer Festival—formerly Taste of Country Fest—announced the lineup for its country music and camping event, taking place in the New York Catskills on June 12-14, 2020. Past GRAMMY nominee Dierks Bentley, current Best Country Album nominee Thomas Rhett, Luke Bryan will headline the three-day event.

Past GRAMMY nominee Kelsea Ballerini, along with Blanco Brown, Gabby Barrett and Clare Dunn will also perform at the fest.

HARDY, Jon Langston, Dylan Scott, Matt Stell, Cole Swindell and The Cadillac Three were also revealed on this first-round lineup, with more artists to be announced at a later date.

"We're happy to bring y'all a brand new festival experience at the same location you know & love. On the grounds of the former Taste of Country Music Festival we're bringing you two stages, 30+ artists and more," TrailBlazer says, via their homepage. Taste of Country was first launched in 2013 at the same location: Hunter Mountain Resort in Hunter, N.Y.

The name change follows an earlier purchase by Live Nation, who adds the event to their growing catalog of country-focused festivals, including Watershed in George, Wash., Faster Horses in Brooklyn, Mich., Seven Peaks in Buena Vista, Colo. and Tortuga Music Festival in Ft. Lauderdale, Fla.

Tickets for TrailBlazer Fest go on sale next Friday, Dec. 13 at 10 a.m. ET; more info at TrailBlazerFest.com.

Kacey Musgraves Wins Best Country Album For 'Golden Hour' | 2019 GRAMMYs

Since Post Malone burst onto the mainstream nearly a decade ago, he has continued to flaunt his genre-defying brand of musical brilliance. For his latest venture, it’s time for gold grills and cowboy hats: Posty’s going country.

Though his musical origins are in rap, Malone has seamlessly traversed pop, R&B, and blues, always hinting at his deep-seated country roots along the way. In the last year, his long-standing affinity for country music has moved to the forefront, with appearances at the CMA Awards, a country-tinged Super Bowl LVIII performance, and a feature on Beyoncé’s COWBOY CARTER. Next up, he’ll make his debut at California's Stagecoach Festival alongside some of country music’s biggest names — and pay tribute to some of the genre greats.

While it’s unclear exactly what the Texas-raised hitmaker will be singing, his 45-minute set on Saturday, April 27 is labeled “Post Malone: Performs a special set of country covers.” After years of performing covers for and alongside country stars, the performance is arguably one of the most full-circle moments of his career thus far.

Ahead of his Stagecoach premiere, read on for some of Posty's biggest nods and contributions to the country music scene over the years — that could culminate in his own country album soon enough. 

A Slew Of Classic Country Music Covers

Malone has a history of channeling his musical heroes, often pulling on his boots to deliver heartfelt covers. He's paid tribute to country icons many times, including covers of Hank Williams Jr.'s classic, "There's A Tear In My Beer” in a 2018 fan-favorite video. 

During a 2022 Billy Strings tour stop at The Observatory in Los Angeles, Malone made a surprise appearance and used the moment to honor Johnny Cash alongside Strings. The pair delivered an acoustic duet of Cash's infamous murder ballad, "Cocaine Blues."

And just this year, Malone covered Hank Williams Sr. during a surprise performance at Nashville's Ryman Auditorium. On April 3, he closed out the annual Bobby Bones' Million Dollar Show with a rendition of Williams' "Honky Tonk Blues." 

A Longtime Kinship With Dwight Yoakam

Malone has long collaborated with Dwight Yoakam, marking a friendship and professional partnership that spans his career. Yoakam is a GRAMMY-winning trailblazer known for his pioneering blend of honky tonk, rock and punk that shook up the country scene in the 80's with his blend of "cowpunk." 

The pair frequently joined forces on Yoakam's SiriusXM Radio spot "Greater Bakersfield," where one standout 2018 appearance features Malone covering Yoakam's own “Thousand Miles From Nowhere” as the two laugh, strum and belt out the lyrics together in perfect harmony. 

On April Fool's Day in 2021, they playfully teased fans with the prospect of a double country album release — which may not seem so far-fetched three years later.

It's fitting that Malone would find such deep inspiration in folks like Yoakam, a man who first rode onto the country scene with a new take on a traditional sound. Much like Yoakam bridged generations with his music, Malone brings a new yet familiar energy to the country scene, embodying the spirit of a modern cowboy in both style and sound.

A Country Tribute To Elvis

Malone teamed up with Keith Urban for a duet rendition of "Baby, What You Want Me to Do" during the "Elvis All-Star Tribute Special," which aired on NBC in 2019. Originally written and performed by blues musician and songwriter Jimmy Reed, "Baby, What You Want Me to Do" was famously covered by Presley and commemorated through Urban and Malone's unique blend of modern guitar-slapping country-rock charisma. 

That wasn't Malone's only country collab that night, either. He also covered Presley's "Blue Suede Shoes" alongside Blake Shelton, Little Big Town and Mac Davis.

A Celebration Of Texas With Country Legends

In March 2021, Matthew McConaughey and his wife, Camila, hosted the "We’re Texas" virtual benefit concert, to help Texans coping with that year's disastrous winter storms during the Covid-19 pandemic. 

Following performances by George Strait, Kacey Musgraves, Willie Nelson, and Miranda Lambert, Malone — who moved to Dallas when he was 10 — served as the night's final entertainer. He performed Brad Paisley's "I'm Gonna Miss Her" followed by Sturgill Simpson's "You Can Have The Crown" backed by Dwight Yoakam.

A Rousing Tribute At The 2023 CMA Awards

At the 2023 CMA Awards, Malone joined country stars Morgan Wallen and HARDY on stage to cover late icon Joe Diffie‘s “Pickup Man” and "John Deere Green." Malone's first-ever performance at the CMAs felt more like a reunion than a debut, with Malone right at home among his collaborators.

“I’ve manifested this for years," HARDY told Audacy's Katie Neal. "Slight flex here, but I started following [Post Malone] when he had like, 300k Instagram followers. I was on the 'White Iverson' terrain, like the first thing that he ever put out and I was like, ‘this is dope,’ and I've been with him ever since.” 

After the performance, Malone hinted to Access Hollywood that it might be the start of a new chapter. When asked if a forthcoming country album would be in the works, he answered, “I think so. Yes, ma'am.” (More on that later.)

A Countrified Appearance At Super Bowl LVIII

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Before Beyoncé announced COWBOY CARTER in a Verizon Super Bowl ad, Malone offered Super Bowl Sunday's first country-themed clue at the top of the night with his tender rendition of "America The Beautiful." Sporting a bolo tie and brown suede, Malone delivered his patriotic performance with a characteristically country drawl while strumming along on acoustic guitar before Reba McIntire's star-spangled rendition of the national anthem. 

Malone's performance followed in the footsteps of a long line of country artists who have kicked off the national sporting event, which started with Charley Pride in 1974 and has included Shania Twain, Faith Hill and Garth Brooks. 

A Tip Of The Hat To Toby Keith

During a performance at the American Rodeo in Arlington, Texas, on March 9, Malone paid tribute to the late Toby Keith, who passed away in February. After pouring one out and taking a sip from a red solo cup (an homage to Keith's playful hit of the same name), Malone performed a cover of "As Good As I Once Was" for the Texas rodeo crowd.

His TikTok video of the performance quickly garnered over 4 million views, sparking enthusiasm among fans for more country music from him. "Sir. I'm now begging for a country album," wrote one user in a comment that has received over 11,000 hearts.

A (Potential) Full-On Country Album

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His much-teased country album may not be too yonder. After confirming that a country album was in the works during a live Twitch stream on his channel, Malone has spent much of this year teasing forthcoming new work. There is no scheduled album release date as of press time, but Malone has shared snippets of new songs including “Missin’ You Like This” and dropped sneak peeks of collaborations with Morgan Wallen, HARDY, Ernest, and Luke Combs. 

In February, Malone posted a sample of a collaboration with Combs, "I Ain't Got A Guy For That," the first in a series of song snippets shared across his social channels. 

On March 20, Malone posted a reel to Instagram featuring a video of himself seated on a stool, smoking a cigarette and singing along to a track that opens with Wallen singing, “It takes two to break a heart in two,” as Malone comes in to deliver a blow with the line, “Baby you blame me, and baby I’ll blame you." The track, shared with the caption (and supposed song title) "I had some help," was first announced in a now-deleted social media post by Wallen at the end of 2023. 

No matter when the album may come, Post Malone’s Stagecoach set will only up the anticipation for some original country music from the star — and from the looks of it, fans and genre stars alike are more than ready for it.

12 Must-See Acts At Stagecoach 2024: Tanner Adell, Charley Crockett & More

After breaking out in the world of contemporary Christian music, Anne Wilson wants to take the country world by storm. 

Out April 19, Wilson's sophomore album embraces the many aspects of her self. Rebel sees the Kentuckian lean into her country and horse farm roots just as she leans into her faith — a subject already deeply intertwined in country music — more than ever before. 

"I’ve never viewed it as switching over to country or leaving Christian music," Wilson tells GRAMMY.com. "With this new record I wanted to write something that was faith-based but also broad enough to positively impact people who don’t have a strong faith as well."

Rebel is just the latest chapter in a journey of triumph and glory first set into motion by tragedy. Wilson started playing piano when she was six but didn’t begin taking it more seriously until the sudden death of her older brother, Jacob Wilson, in 2017. Despite the weight of the moment, Wilson, then 15, returned to the piano to channel her grief — a move that culminated in her first live singing performance when she belted out Hillsong Worship’s "What A Beautiful Name" at his funeral.

"My life forever changed in that moment," admits Wilson. "I already knew that life was very short on this side and that we only have a small window of time here so I wanted to make mine count. It was a special, but really hard moment that has gone on to spawn my entire career. Hearing just how much my songs have impacted fans makes me feel like his tragedy wasn’t wasted and that it was used for good."

Soon after she posted a cover of "What A Beautiful Name" to YouTube that netted over 800,000 views and caught the attention of the brass at Capitol Christian Music Group, who promptly signed her to a deal. Her first release with them, My Jesus, earned a GRAMMY nomination in 2023 for Best Contemporary Christian Music Album in addition to its title track hitting the top spot on Billboard’s Christian Airplay chart. 

Similar to My Jesus, Rebel sees Wilson doubling down on her religious roots while continuing to preserve the memory of her beloved brother. Although she grew up in a devout Christian household in Lexington, Kentucky, Wilson says that she didn’t fully connect with her faith until Jacob’s passing. 

Nowadays she couldn’t see herself living without it.

"When it came to dealing with the loss and tragedy of my brother I knew I couldn’t have survived that without [faith]," she says. "As I started writing songs and moved to Nashville my faith quickly became everything to me."

The 16-song project hits the bullseye between contemporary Christian and country twang, with an assist from special guests including Chris Tomlin ("The Cross"), Jordan Davis ("Country Gold") and Lainey Wilson ("Praying Woman"). Of the Lainey feature, Wilson says the two wrote "Praying Woman" upon their first day of meeting, with the elder Wilson growing into big sister and mentor of sorts for Anne. The song was inspired by the power of prayer Wilson and Lainey each experienced from their mothers growing up.

"We’d been talking about memories from growing up and remembering our mother’s coming into our rooms, getting on their knees and praying for us," recalls Wilson. "There was a conviction in how they prayed and expected them to be answered that was so powerful and special that we wanted to capture the feeling of it in song."

Rebel's strong motherly influence continues on "Red Flag," a rockin' number that Anne Wilson wrote as guidance to her younger fan base about what to look for in lasting love. While she largely had to ad lib the concept, having no bad breakup or relationship experiences to pull from, many of the "green flags" she notes were the result of years of advice. Things like going to church, being down to Earth, hunting, fishing, and respecting the American flag were traits and hobbies Wilson's mother had been passing down to her for years.

"Growing up she was always teaching me about relationship red and green flags, what to expect and to never settle," explains Wilson. "I have a song on my last record called ‘Hey Girl’ that ['Red Flag' is] almost a continuation of. It started out as a fun joke and turned out to be an actual serious song about red flags that’s one of my favorites on the whole record."

Another tune that began lighthearted before adopting a more serious tone is "Songs About Whiskey." Playing into country music and her home state's obsession with songs about brown liquor, the upbeat banger is intended to instead illustrate how Wilson gets her high from G-O-D rather than A-B-V or C-B-D through lines like, "I guess I’m just kind of fixed on/ The only thing that’s ever fixed me/ That’s why I sing songs about Jesus/ Instead of singing songs about whiskey."

"It’s supposed to be fun, make you laugh and fill you with joy," describes Wilson. "But it’s also meant to show how my faith is my true north, not those other things that are going to try to fill you up, but never do."

Through all of Rebel Wilson not only proves how her faith is her true north, but also shows others yearning to get there a path toward. This feeling culminates on the record’s title track, which frames her open love of Jesus as an act of rebellion in today’s world. A lesson in "what it means to have faith, not backing down from it and clinging to what we know is true," Wilson says the song was also inspired by previously having a song turned away at Christian radio for sounding "too country."

"I’m not going to try to please Christian music and I’m not going to try to please country music, I’m just going to be who I’ve always been and let the songs fall where they want to," asserts Wilson. "That was fuel not just for the song, but going against the grain on this entire album to be my most authentic self yet."

At the end of the day, genre labels, accolades and being included in the Grand Ole Opry’s NextStage Class of 2024 are secondary to Wilson’s adoration for the man above and her brother who, albeit tragically, set her on the journey she’s on now.

"I want to make sure I’m honoring him in everything that I do," reflects Wilson, "because he’s the reason I started doing music in the first place." 

Inside Tyler Hubbard's New Album 'Strong': How He Perfectly Captured His "Really Sweet Season" Of Life

Last August, Oliver Anthony became the quintessential definition of overnight success. His working class anthem "Rich Men North of Richmond" went from viral sensation to history-making hit, helping the singer become the first to top the Billboard Hot 100 without any prior chart history.

But while "Richmond" showcases Anthony's brutally honest songwriting and raw delivery, its message and success are far from what define him. And he's proving just that with his debut album, 'Hymnal Of A Troubled Man's Mind.'

Helmed by Nashville superproducer Dave Cobb, the 18-track collection is rife with stories of addiction, depression, faith, and fury as Anthony documents the decade leading up to his unexpected rise to stardom (it also features eight Bible verses as interludes). A stark departure from "Richmond" in some ways and others not, the album is proof that his viral moment wasn't a fluke. 

One element that remains is Anthony's defiance of adhering to any cookie-cutter artist blueprint, which was further evidenced by the Easter Sunday arrival of Hymnal Of A Troubled Man's Mind. It's one of the many ways Anthony is showing that he's still fiercely independent, and that his unprecedented ascent hasn't changed the man he is or the music he makes.

"My day-to-day life hasn't changed a whole lot other than just not having to wake up for my job every morning," Anthony — who was born Christopher Anthony Lunsford, but pays tribute to his late grandfather with his stage name — admits. "I have this new career, but at the same time I don't know how long I'll be doing this either. At the end of the day I want to truly make a difference, not just play a bunch of shows to make a handful of executives a bunch of money only to get a pat on the back."

On the heels of releasing Hymnal Of A Troubled Man's Mind — and playing a sold-out hometown show — Lunsford spoke with GRAMMY.com about how he's navigating the balance between fame and privacy, and staying true to himself through it all.

Your stage name is your grandfather's name, so he clearly means a lot to you. Can you tell me a bit about the man Oliver Anthony was, and why he inspired you to pay tribute to him in such a way? 

Originally I was using his name as an alias because a lot of the songs I was writing talked about things my employer wouldn't approve of, like smoking pot. It was a way of hiding my identity so they couldn't Google my name and find everything. 

Another reason I did it is because we looked a lot alike. I'm the only redhead in the family other than him, and we're both 6'6" and left-handed. 

He was also just a very down-to-Earth guy. He never was one to talk much and never took the bait on politics and other stuff, he was always very down the middle. He was a hard worker too, taking a job later in life at a chemical plant where he moved up in the ranks despite being mostly self-taught. 

He was a role model of mine in many ways. During his final years, he experienced cognitive decline that made his death more of a slow goodbye. When I started writing all of these songs I was still really grieving his loss.

The full listing of your stage name, at least in the beginning, was Oliver Anthony Music. What was your intention with adding the "Music" part onto it?

The "music" is supposed to capture the timeless era from the beginning of the Industrial Revolution to into the late 60's and 70's. I'm not trying to paint it as an ideal time in American history by any means, but it was just a very real time. People weren't just living then, they were surviving. I wanted to capture that era of America before we became reliant on ordering everything from Amazon, going to the grocery store for all our food and depending on people on TV to tell us how to think, where to go or what to do.

That's what Oliver Anthony Music is supposed to encapsulate — that precious time in our history that, in certain parts of the country, still exists. When you go into rural Virginia, West Virginia, Kentucky and the Carolinas, it almost feels like time is slowed down a bit, almost like they're 20 or 30 years in the past. 

That's why we recorded this album on 1940's microphones inside an old church. We didn't even hire a photographer for the album cover. Instead we used a Polaroid camera that Dave Cobb had sitting in his drawer. This was never intended to have all the flash of modern production. It's supposed to just be as raw, from the heart and sincere as it can be.

Is "Rich Man's Gold" a song about your grandfather and how the circumstances of his upbringing shaped him into the man you remember? 

It also focuses on the contrast between the lifestyle we live now compared to the one we lived not long ago. The main verse in the song talks about how we weren't born to just pay bills and die. The point behind that is so many people today have encapsulated their lives in student loans, credit card debt, financing new vehicles they don't need, and buying big houses as a way of filling a void they'll never be able to fill. 

I think true fulfillment in life comes from basic things we overthink, like love and connection with our family, neighbors and friends, and just living a more purposeful life. A lot of us go to work at a job we don't really like because it pays the bills, even though it falls well outside our passion, leaving us only a couple hours a week to spend doing what we truly love. Then before you know it, you're old and die and that's it, you don't get another shot at it. 

Time is the most precious thing we have, and at any moment we don't really know how much left of it we have. The song really hones in on all that to show how a lot of people are alive, but they're not really living.

How has the overnight success you've experienced changed, or not changed, who you are as a person? 

I've kept a lot of my same friends and would say that my personal life hasn't changed a whole lot. I've still got the same s—ty Suburban with a salvage title and 330,000 miles on it, and the same s—ty clothes — although I have been able to put money into a few investments to set my family up with some financial security. But I've been really careful not to change my life a lot. 

I never, ever want to get to a point in my life where I feel like I'm better than everyone else. It makes me sick to my stomach just thinking about it. That's one thing that's been a problem from the beginning because I never wanted to get on Facebook and say "Hey, look at me!" When "Richmond" blew up, I didn't want to post a lot, and instead opted to let things run their course. But due to the monetization of social and online media, people were incentivized to make posts about me since I was a trending topic, with much of it being completely fabricated. 

So it's been a weird balance of figuring out how I can, with good conscience, keep my voice out there without being an attention seeker. It's a weird balance because if I'm not posting and speaking my mind, then somebody else pretending to be me is going to do it instead.

I really just want to use what little discernment I have to make decisions that I'll look back on in 20 or 30 years and feel proud of, and not like somebody strong-armed or pressured me into something that my heart wasn't into.

One of the ways you showed that after going viral was by promoting other amazing Appalachian artists that RadioWV has featured. Who are some Appalachian artists you've been listening to or think deserve a bigger platform for their music?

To be honest, what I listen to is pretty limited and is mostly made up of people who are dead. I mainly discover new music through YouTube videos — I don't have Spotify, Pandora or anything like that. I've had the chance to meet and talk with folks like Logan Halstead, and am a big fan of his work, though. 

It drives my wife absolutely crazy, but anytime we're in the truck together and I've got control of the dial I'm putting on Hank Jr., Waylon Jennings, Jerry Lee Lewis, Lightnin' Hopkins and random stuff like Cuban dance music. I like listening to a lot of old material and folk music from other countries. It just feels more real, and nobody is trying to shove it down my throat. 

At least when I'm listening to somebody who's dead, I know that they didn't manipulate me to somehow stumble across it like how so much is today with algorithms and pay-to-play. That's also what was so cool about "Richmond," because it blew up in such an organic way with no record label or management pushing it. 

Getting back to your original question about Appalachian artists, there's so many people from the region that would blow the doors off anyone on country radio right now, that most people may never actually get to enjoy because they simply aren't getting the exposure. I'd love to see things go back to the days of good music being played and bad music doesn't rather than it all being about how much money you've got behind the song.

You previously hinted at getting into ministry in the future, and this new album of yours is littered with Bible verses. With that in mind, what does your foundation in faith mean not only to your music, but who you are as a person? 

Leading up to everything that's happened, it's obvious from listening to my music that I was severely depressed and dealing with regular suicidal thoughts and anxiety attacks. Every part of my life, from my career to my marriage, my family and my future seemed very grim. I was in a bad place leaning on alcohol, like a lot of adult men do, because they have a tough time opening up about their struggles. 

At some point I got in touch with Draven Riffe from RadioWV and made plans to record a few songs on my property the following weekend. We got to talking about the personal issues going on in both our lives and how we'd both just decided to give our lives to God. I felt like I didn't have anything left in me, so I just told God that I've done things this long by myself and haven't been able to figure anything out, so please guide me where to go and show me what to do. 

I ended up recording seven songs with Draven that weekend, but the most special moment definitely came on "Richmond." As soon as we finished recording, I looked up at him, and we locked eyes. After a moment he said, "I know we just met and I don't want you to think I'm crazy, but I swear I could feel the presence of God with us when we recorded that." 

The song ended up doing what it did, but the icing on the cake came months later during my first show after going viral at the farmer's market where over 12,000, including Jamey Johnson, showed up. I talked with him afterward and he told me he had been off songwriting but that God spoke to him and told him he needed to meet me that day. To have one of my favorite artists of all-time show up at my first gig because God told him to after everything I'd been through, it became so clear to me that I was doing what I was meant to. 

A lot of people joke that they sell their souls to the devil, but in my case I truly feel like I've signed my soul to God. He put me here to give me purpose because my life had been without it up until then. 

I don't know that I'd even call myself a Christian, but I definitely believe in Jesus Christ and find a lot of wisdom in the timeless knowledge of The Bible. There's parts of Proverbs, Ecclesiastes, and Matthew — all of which have excerpts on the record — that are full of practical advice on living, whether it's with marriage or finances, lust or alcoholism, or even how to interact with your neighbor. That advice written many years ago is still so relevant in today's society even though most things are totally different. 

My first time in a church in 10 years was for our Easter show the other day, so I'm definitely not the church-going devout religious kind of person. I just got to a point in my life where I didn't have any other choice than to let God take control of things. You can see just how much change has happened since then — it's undeniable.

Aside from ministry, is there anything else you want to pursue with your newfound platform?

Our family just bought this old farm that was operational until a couple years ago. We're in the process now of getting it going again. Once it's operational we want to start educating the public and maybe bringing people out for workshops on gardening and other homesteading basics. 

I also want to partner with other people in that space, like Joel Salatin, or some of these YouTubers that are getting people excited about gardening on only a quarter-acre in their backyards. It tastes better than anything you can buy — even at a high-end grocery store — and can be done for little to nothing. It's so rewarding to do and something I hope to repopularize as part of this whole thing.

It sounds like you're really trying to practice what you preach in terms of what you sing about and how you embody that spirit in everything you do.

Music and my whole life in general is just trying to hold on to that beautiful, raw, less glorified and flashy way of living that's still readily available in this country. There's so much noise and everything moves so quick now that it's hard to slow your brain down enough to get excited about gardening, being outdoors and clearing the land or raising livestock. There is no instant gratification to that, it's a process. 

If you get on YouTube and scroll through 100 Shorts your mind will start going a million miles per hour, which makes it hard to want to slow down to clean up after some stupid cow afterward. It makes it very hard to integrate the two things together into how we live today. 

What has making this music taught you about yourself? 

One thing I've learned is that if I want to try to have good mental health and be a normal functioning member of society, I've got to create music. In the same way that some people use a journal to write out their thoughts, songwriting is how I'm able to get my feelings and perceptions out of my own head. When life is going really well, it's harder for me to write songs because usually my motivation stems from things going wrong. I could probably write some catchy lyrics, but they wouldn't mean anything to me. 

Everything I write about I feel deep down inside, which can also be said about some of my favorite songs. That's the beauty of music — writing it as a way to clear your head and listening to it to remind you that you're not alone.

8 Artists Bringing Traditional Country Music Back: Zach Top, Randall King, Emily Nenni & More On Why "What's Old Becomes Beloved Again"

We may have known about Toby Keith's stomach cancer diagnosis for nearly two years, but that didn't keep the news of his Feb. 5 death from hitting hard. The oftentimes outspoken country music star enjoyed a three-decade career as one of the genre's beloved hitmakers, courtesy of unabashed hits like "Who's Your Daddy?," "Made In America" and "I Wanna Talk About Me."

Occasionally his in-your-face persona clashed with folks, particularly when it came to his political views in recent years. But for the most part, it was Keith's blue-collar upbringing and work ethic that shined through and resonated with his legion of listeners. 

It wasn't until his thirties that the future Songwriters Hall of Famer landed his first record deal in 1993, following years grinding away as a rodeo hand, in oil fields and as a semi-professional football player to make ends meet. The Oklahoma-born crooner would go on to record 20 No.1 hits, sell over 40 million records across 26 albums, and gross nearly $400 million touring — cementing himself as one of country music's most successful artists in the process.

As we look back on Keith's life and legacy, here are five essential cuts from the seven-time GRAMMY nominee, whose memory will live on in the hearts of country music artists and fans alike.

"Should've Been A Cowboy" (1993)

Few artists strike gold with their maiden release, but Keith did just that when his song "Should've Been A Cowboy" launched in February 1993. The upbeat track received widespread acclaim, eventually reaching No. 1 on the Billboard's Hot Country Songs chart a few months later.

"Should've Been A Cowboy" takes on a distinctly traditional tone as Keith romanticizes cowboy culture by referencing classic westerns like Gunsmoke with nods to Marshall Dillon and Miss Kitty in addition to six-shooters, cattle drives and Texas Rangers abound. The tune also reinforces the notion that cowboys just have more fun, whether its "stealin' the young girls' hearts, just like Gene [Autry] and Roy [Rogers]" or "runnin' wild through the hills chasin' Jesse James." 

By the looks of Keith's career, he certainly had his fair share of fun, and it may not have come if it weren't for "Should've Been A Cowboy."

"How Do You Like Me Now?!" (1999)

After a successful '90s run (which included two more No. 1s in "Who's That Man" and "Me Too"), Keith kicked off the 2000s with his fourth No. 1 hit, "How Do You Like Me Now?!" In signature Toby Keith fashion, he confronts his haters by asking the titular, rhetorical question, posed to his high school's valedictorian — who was also his crush. "I couldn't make you love me but I always dreamed about livin' in your radio," he sings on the brazen chorus.

The song is a stern reminder to never let anyone keep you from chasing your dreams; it's also a lesson of standing strong on your convictions. Its message also proved fitting for Keith's career: After Mercury Records Nashville rejected the song (and its namesake album) in the late '90s, Keith got out of his deal with them in favor of signing with DreamWorks Records, with whom he released the project a year later. Not only did the single go on to spend five weeks at No. 1 on the Hot Country Songs chart, but it became the singer's first major crossover hit.

"Courtesy of the Red, White and Blue (The Angry American)" (2002)

Keith was never afraid to share his opinion in public or in song, especially when it came to displaying his patriotism and appreciation for those who protect the United States. While the Okie approached this from a softer side on 2003's "American Soldier," his most renowned musings on the subject without a doubt came a year earlier with "Courtesy of the Red, White and Blue (The Angry American)."

On the angsty ballad — which was written in the wake of his father's March 2001 death and the Sept. 11, 2001 terrorist attacks — Keith channels a universal feeling of American hurt and pride. "Courtesy of the Red, White and Blue (The Angry American)" inspired an equal outpouring of support and outrage that, for better or worse depending on where you stand, helped cement the song into the annals of country music lore.

"I Love This Bar" (2003)

We've all got our favorite watering hole full of its own quirks and characters, from winners to losers, chain-smokers and boozers. Keith taps into that feel-good, hometown hang feeling with "I Love This Bar," a lighthearted tale from 2003's Shock'n Y'all that makes dingy dive bars feel like the prime party destination.

The midtempo track — Keith's 12th No. 1 — further plays into country music drinking tropes as Keith proclaims, "I like my girlfriend, I like to take her out to dinner, I like a movie now and then" before making a hard pivot, adding "but I love this bar." 

All joking aside, the song, and all of the unique individuals described within it, have a harmony to them inside those hallowed walls. It's a kinship that seems more and more difficult to find in today's world, and a sentiment best captured at the song's conclusion: "come as you are."

"As Good As I Once Was" (2005)

Your best days may be behind you, but that doesn't mean you can't still live your best life and thrive in the present — even if you don't get over hangovers as quickly as you used to.

That youthful wisdom is distilled into every lyric of "As Good As I Once Was," a reminiscent story in which a then-44-year-old Keith recounts his prime as a lover, drinker and fighter humbly. That being said, his pride is still quick to take charge with convictions like "I still throw a few back, talk a little smack, when I'm feelin' bullet proof."

Lasting six weeks at No. 1, "As Good As I Once Was" was the biggest of the 15 chart-toppers Keith tallied in the 2000s. And though he scored one more in the following decade (along with several other hits, including the playful drinking song "Red Solo Cup"), "As Good As I Once Was" will live on as one of Keith's quintessential messages of fun-loving confidence: "I ain't as good as I once was, but I'm as good once, as I ever was."

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