Nashville may be known as Music City to most, but to those in the music industry, it's the "10-Year Town." While overnight successes can happen, for most creatives, it's a slow and steady climb — and in Nashville specifically, the story often goes that it takes a decade before catching that big break.

Acts like reigning ACM and CMA Female Vocalist of the Year Carly Pearce and CMA New Artist of the Year (and 2022 Best New Artist GRAMMY nominee) Jimmie Allen — who moved to Nashville in 2009 and 2007, respectively —  are a testament to this adage. So is rising star Hailey Whitters, who even wrote a song titled "Ten Year Town" in 2017; she proclaims in the final verse, "This next song could turn it all around."   

The 32-year-old singer/songwriter is part of country's latest class of artists who are making waves years after their start in Music City. That class includes Walker Hayes, whose "Fancy Like" went from TikTok sensation to GRAMMY-nominated No. 1 hit last year — 17 years into his time in Nashville —  and Jameson Rodgers, who saw his first No. 1 as a singer with 2020's "Some Girls" 10 years after he moved to Music City. 

"I compare it to going to law school or medical school," Rodgers says. "It takes moving here and meeting as many people as possible. It takes being poor for a few years while you work on your craft. The early years prepare you for what's to come. It's a crazy dream to chase, but I'm really glad I did it."

Below, discover the journeys of Whitters, Hayes, Rodgers, and five more of their country cohorts, and hear their testimonials on why the Nashville grind is worth it. 

ERNEST

Hometown: Nashville, TN

Signed label deal: 2018

Big break: "Flower Shops," a duet with Morgan Wallen, broke the top 20 on Billboard's Country Airplay chart in June 2022

ERNEST has been writing songs since middle school and credits a trip to the Grand Ole Opry in the fourth grade for further igniting that fire for music. "Even as a fourth grader I was like, 'I want to do this one day,'" he recalls.

The singer saw early success co-penning No. 1 songs for Chris Lane ("Big, Big Plans"), Morgan Wallen ("More Than My Hometown") and Sam Hunt ("Breaking Up Was Easy in the 90s") but it was his Flower Shops (The Album) that set the bar even higher. "With the Flower Shops album, I've come into full form as my country artist self," he says. "I'm still going to be growing always and evolving, but this is me. This album is me, and I'm here."

Though he's a native Nashvillian, ERNEST says 2022 marks 10 years since he began pursuing music. Fittingly, he agrees that Nashville is a 10-year town. "Obviously there are people that have success super early on and get that lucky break immediately but as [hit songwriter and Big Loud Records Partner] Craig Wiseman said, 'Everybody pays their dues — you either pay them at the beginning, or pay them at the end.'"

Hailey Whitters

Hometown: Shueyville, IA

Arrived in Nashville: 2007

Signed label deal: 2020

Big break: 2020's The Dream, which Whitters self-funded and self-released

Hailey Whitters picked up the guitar at 14 and has been writing songs ever since. Whitters' earliest influences include '90s country radio titans Alan Jackson, Trisha Yearwood, the Chicks and Tim McGraw. Little did she know that decades later, she'd have her songs recorded by Jackson, Martina McBride and Little Big Town. 

"Growing up adoring country radio, I think I knew early on [I wanted to be an artist] — but I had no idea how to go about it, because no one from my town had ever tried," Whitters says. "I had a guidance counselor in elementary school tell me if I wanted to be a country music star, I had to learn how to write my own songs, so I started doing that."

Whitters' relatable storytelling on songs like the autobiographical (and fittingly titled) "Ten Year Town" eventually caught the attention of Music Row, and she signed with Big Loud Records' female-driven imprint Songs & Daughters in 2020. Her infectious breakthrough single, "Everything She Ain't," goes for adds at country radio June 27 — nearly 15 years after she relocated from her native Iowa to Nashville. 

So, what's Whitters' opinion on the 10-year town philosophy? "Everyone's experience is different," she says. "I will say in my time here, I've found that most things that last weren't the things that happened overnight."

HARDY

Hometown: Philadelphia, MS

Arrived in Nashville: 2010

Signed label deal: 2018

Big break: "One Beer" feat. Lauren Alaina and Devin Dawson hit No. 1 on Billboard and Mediabase charts in December 2020

HARDY never intended to be an artist. As a teenager, he learned about songwriters and became a fan of Rodney Clawson, Casey Beathard, Eric Church and Brad Paisley. He started writing songs at 17, and in the nearly 14 years since, he has authored 10 No. 1 songs including Blake Shelton's "God's Country," Florida Georgia Line's "Simple," Morgan Wallen's "Up Down" and Dierks Bentley's "Beers On Me." But it wasn't until producer Joey Moi reached out that his career path changed. 

"He was my favorite producer of all time," HARDY says. "He had just produced 'Up Down,' and it was climbing up the charts, and he called me and said, 'Dude, if you ever wanted to cut a record, I would love to cut a record [for] you.' A switch flipped in my head, and I said, 'Okay, let's do this.'" 

While he's managed to earn two No. 1s as an artist in his own right, HARDY feels he hasn't arrived quite yet. "I think a lot of artists never really have that moment," he says. "Part of their muse and part of what drives them and keeps them going is always looking for something more."

Jameson Rodgers

Hometown: Batesville, MS

Arrived in Nashville: 2010

Signed label deal: 2018

Big break: "Some Girls" reached No. 1 on Billboard and Mediabase in October 2020

Jameson Rodgers can't remember a time when he wasn't singing. As a kid, he'd walk around school belting Travis Tritt's "Here's a Quarter" and other '90s hits. His first musical memory is a Garth Brooks show at the Pyramid in Memphis, TN, at age 5. "He used to break his guitar on stage every night back then," Rodgers says. "Seeing him do that, as a young kid, I felt like I knew I wanted to do that someday, but I was too young to process it."

Rodgers picked up guitar in college and began writing songs. An Eric Church show during his freshman year reaffirmed the feeling that Garth had inspired: "I knew that I had to chase this dream."

He didn't know anyone when he moved to Nashville in 2010, so he went to every open-mic night he could and quickly made friends with HARDY, Hunter Phelps and Jordan Davis. He's since had two No. 1 songs as an artist with "Some Girls" and "Cold Beer Calling My Name" (a duet with Luke Combs), as well as co-written Chris Lane's No. 1 hit "I Don't Know About You" and songs for Florida Georgia Line, Jason Aldean and Luke Bryan.

Lainey Wilson

Hometown: Baskin, LA

Arrived in Nashville: 2011

Signed label deal: 2018

Big break: "Things a Man Oughta Know" hit No. 1 on Billboard and Mediabase in September 2021

Lainey Wilson's success story is practically the definition of the 10-year town sentiment: In September 2021, 10 years and one month — nearly to the day — that she moved to Nashville, her debut single, "Things a Man Oughta Know," hit No. 1 on the Billboard and Mediabase country radio charts. (Thanks to her 2022 Cole Swindell collaboration, "Never Say Never," she's already notched her second chart-topper.)

"I've been blessed with several milestone 'pinch me' moments, especially within the last year, and I feel like I'm always going to be a work in progress," Wilson suggests. "I don't know if I'll ever feel like I've fully arrived. But I will say, when my deddy [sic] called the first time he heard my song on the radio, that was a pivotal moment."

Wilson first performed in public at her kindergarten graduation. Even at just 5 years old, she knew she wanted to sing for the rest of her life.

"I wrote my first song at 9 years old and took a family vacation to Nashville," she recalls. "I remember exactly where I was on the interstate with my family when I said, 'This is home.' I knew in my heart I was going to be a part of the country music family in some way. I've never had a doubt."

Shy Carter

Hometown: Memphis, TN

Arrived in Nashville: 2011

Signed label deal: 2020

Big break: 2021's The Rest of Us EP, which has garnered more than 12 million streams on Spotify

As a songwriter, Shy Carter has co-written countless country hits like Kane Brown's "Heaven" and "Good As You," Keith Urban's "Never Coming Down" and "God Whispered Your Name," and Sugarland's "Stuck Like Glue." While he knew he wanted to be an artist from a young age, singing along to songs in his bedroom, it took years of writing hits for other artists before his artist dream came to fruition. 

In 2020, he released his spirited debut single, "Good Love" and landed on MusicRow's "Top 100 Songwriters of 2020" list. The Rest of Us EP followed in 2021, and included the raucous ode to a night out with his buddies, "Beer With My Friends," featuring Cole Swindell and David Lee Murphy. To date, he has amassed 35 million streams worldwide across all on-demand DSP platforms.

"I've had a particular vision for how I want the music to feel and how I want to bring people together from all different walks of life," Carter says of his artist career. "There have been a lot of wonderful things happening in my career, and I'm so grateful for all of it. But there's a lot more to me as an artist, and I'll be arriving live in living color very soon."

While Carter agrees that Nashville is a 10-year town, as it has taken him a decade to launch his artist career, he says there are exceptions. "I have seen some people blow up really fast, and I'm glad to see it! I'm happy to take the journey slow and steady and soak up every moment."

Tenille Townes

Hometown: Grande Prairie, Alberta, Canada

Arrived in Nashville: 2014

Signed label deal: 2018

Big break: "Somebody's Daughter" reached the Top 30 on Billboard's Country Airplay chart in May 2019

When Tenille Townes was 9, Shania Twain pulled her up on stage to sing. "That lit a fire in me and made me believe anything was possible," she remembers. 

By 14, Townes was traveling back and forth to Nashville. Ten years later, in 2018, she signed with Columbia Nashville and caught attention with her thoughtful songwriting and powerful story songs "Somebody's Daughter" and "Jersey On the Wall (I'm Just Asking)." 

Both tracks topped the Canadian Country Airplay charts while "Somebody's Daughter" peaked at No. 26 on Billboard's Country Airplay chart. Named the 2020 ACM New Female Artist of the Year, Townes' star has only continued to rise. By 2021 her Jay Joyce-produced debut album, The Lemonade Stand, was named Country Album of the Year at the JUNO Awards in her native Canada. A believer in the 10 year town adage, Townes says Nashville continues to embrace and inspire those who are brave enough to keep showing up.

"It's a welcoming community, and at the same time it's also hard to not bend and shift your shape to fit in," she says. "I also believe there's validity in the 10,000-hour theory, and that arriving to a solid foundation of your craft is connected to the time you put in — however many years that amounts to in any town."

Walker Hayes

Hometown: Mobile, AL

Arrived in Nashville: 2004

Signed label deal: 2017

Big break: "Fancy Like" hit No. 1 on the Billboard and Mediabase country charts in July 2021

"Nashville, to me, is a 17-year town," Walker Hayes says. "It is not a town you come and conquer overnight. There's really no such thing as an overnight success. 'Fancy Like' did pop overnight, but it took multiple jobs, a lot of heartbreaks, financial woes that I don't ever want to go back and relive."

It took nearly two decades and three record deals before Hayes achieved a No. 1 single with "Fancy Like." Hayes (who had moderate success with 2017's "You Broke Up With Me" which peaked at No. 10 on Billboard's Country Airplay chart), admits his story isn't the norm, as he didn't play his first show until he was 23 at local Mobile bar the Yacht Club — a night he says "changed my life." 

When he and his wife came back from their honeymoon, the couple drove their U-Haul to Nashville. Two weeks later, Hayes found himself at Nashville's preeminent listening room, the Bluebird Café, where he was introduced to the magic of songwriting. He walked out of the venue having written his first song and hasn't stopped since.

"I wouldn't change my journey for the world," Hayes says. "To me, the adventure is what's priceless. That's what shapes us. I'm so grateful for how the journey has unfolded."

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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.

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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." 

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From commanding stages to blasting through stereos, countless women have globally graced the music industry with their creativity. And though they've long been underrepresented, tides are changing: in just the last few years, female musicians have been smashing records left and right, conquering top song and album charts and selling sold-out massive tours.

This year, Women's History Month follows a particularly historic 66th GRAMMY Awards, which reflected the upward swing of female musicians dominating music across the board. Along with spearheading the majority of the ceremony's performances, women scored bigtime in the General Field awards — with wins including Best New Artist, Record Of The Year, Song Of The Year, and Album Of The Year.

Female empowerment anthems, in particular, took home major GRAMMY gold. Miley Cyrus' "Flowers" took home two awards, while Victoria Monét was crowned Best New Artist thanks to the success of her album Jaguar II and its hit single "On My Mama." As those two songs alone indicate, female empowerment takes many different shapes in music — whether it's moving on from a relationship by celebrating self-love or rediscovering identity through motherhood.

The recent successes of women in music is a testament to the trailblazing artists who have made space for themselves in a male-dominated industry — from the liberating female jazz revolution of the '20s to the riot grrl movement of the '90s. Across genres and decades, the classic female empowerment anthem has strikingly metamorphosed into diverse forms of defiance, confidence and resilience.

No matter how Women's History Month is celebrated, it's about women expressing themselves, wholeheartedly and artistically, and having the arena to do so. And in the month of March and beyond, women in the music industry deserve to be recognized not only for their talent, but ambition and perseverance — whether they're working behind the stage or front-and-center behind the mic.

From Aretha Franklin's "RESPECT" to Beyoncé's "Run the World (Girls)," there's no shortage of female empowerment anthems to celebrate women's accomplishments in the music industry. Listen to GRAMMY.com's 2024 Women's History Month playlist on streaming services below.

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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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