meta-script5 Black Artists Rewriting Country Music: Mickey Guyton, Kane Brown, Jimmie Allen, Brittney Spencer & Willie Jones | GRAMMY.com
5 Black Artists Rewriting Country Music: Mickey Guyton, Kane Brown, Jimmie Allen, Brittney Spencer & Willie Jones

(L-R): Willie Jones, Kane Brown, Mickey Guyton, Brittney Spencer, Jimmie Allen

Photo credit for source images (L-R): Matthew Berinato, Matthew Berinato, Phylicia J.L. Munn, John Shearer

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5 Black Artists Rewriting Country Music: Mickey Guyton, Kane Brown, Jimmie Allen, Brittney Spencer & Willie Jones

Despite inventing country music, Black artists have historically been marginalized in that sphere. That's all changing in the 21st century with the help of country music stars like Mickey Guyton, Kane Brown, Jimmie Allen, Brittney Spencer & Willie Jones.

GRAMMYs/Jul 26, 2021 - 10:30 pm

2021 has introduced a dynamic change to American life that has aggressively called into question stereotypes surrounding race, gender and culture. And there may be no better lens through which to examine this development than in country music. 

For almost a century, the Appalachia-born genre, more than almost any other subset of American popular music, has largely excluded Black artists and performers. However, the roots of country music lay in the hands of banjo-playing Black slaves and minstrel-show performing sharecroppers. 

Still, for well over 50 years, the only Black artist significantly represented in the country music industry was the late Charley Pride, who died last December. The Mississippi-born sharecropper turned All-Star Negro League pitcher's ability to navigate his way around a country song led to four dozen-plus top 10 Billboard Country chart hits (including the 1971 classic "Kiss An Angel Good Morning") and worldwide appeal.

Today, in an era partly defined by reparational justice toward African-Americans nationwide, country music contains numerous performers whose tireless efforts in the genre are now being rewarded. Of the growing crowd, Mickey Guyton, Kane Brown, Jimmie Allen, Brittney Spencer, and Willie Jones have all received Pride-level applause for their successes within country music.

Read More: For Charley Pride, Black Country Music Was A Self-Evident Truth

Country's Next Great Torch Singer: Mickey Guyton

From Patsy Cline to Carrie Underwood, country music has a tradition of white female vocalists whose impressive vocal control and electrifying histrionics elevate superb songwriting to award-winning levels.

Comparatively, warm, soulful singers like Linda Martell and Rissi Palmer have opened doors for Black female country performers.

For those looking for a marriage of the two, Mickey Guyton—a veteran country artist buoyed by the pained yet profound inspiration of the Black Lives Matter movement—married her multi-octave superstar vocal instrument to the poignant ballad "Black Like Me" and has soared to top-tier country acclaim. Her new album, Remember Her Name, drops on September 24.

Country music is often maligned because of its inability to address issues of race and gender in a manner that befits the tenor of progressive times. However, Guyton's now-signature song overcame the genre's historical slights against marginalized communities. What's more, it reflects country music's slow, continued moves toward justice for them.

A "Worldwide Beautiful" Superstar In The Making: Kane Brown

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Kane Brown is the type of artist as comfortable making modernized trap-style country ballads (2020's "Be Like That," featuring Swae Lee) as he is covering the neo-traditionalist Randy Travis' classic "Three Wooden Crosses."

His head—frequently topped with an adjustable trucker hat—has growing ears, eyes and music-biz savvy. Recently, the trailer-park-raised Chattanooga, Tennessee, native launched a new label, Sony-backed 1021 Entertainment—plus a song publishing company, Verse 2 Entertainment. 

However, if looking for the accurate measurement of Brown's cross-cultural reach, "Worldwide Beautiful" drives home why Brown is a star of note, with an extraordinarily passionate social media following to boot.

When he sings, "At every show I see my people/They ain't the same, but they're all equal/One love, one God, one family," his rich tenor conveys a unifying message that supersedes today's American frustrations and antagonism.

The Hometown Hero: Jimmie Allen

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Country music loves stories of self-made small-town boys with humble dreams that shine under Music City's downtown Broadway lights.

To wit, rising country star Jimmie Allen is a native—and still, proudly a resident—of Milton, Delaware, a town populated by a hair below 3,000 people. His new album, Bettie James Gold Edition—an expansion of his Bettie James project—dropped in June.

Within the first five years of his country career, Allen's achieved two platinum-selling, number-one Billboard Country Airplay chart singles (2018's "Best Shot" and 2019's "Make Me Want To"), plus recently became the first Black artist to win the New Male Artist of the Year award at 2021's Academy of Country Music Awards.

It's also notable how Allen carries forth Charley Pride's legacy. In a 2020 interview for Holler, the vocalist noted that the Country Music Hall of Famer taught him that if he made the music he loved, "It'll land on the ears and hearts of the people who are supposed to hear it."

"[That advice] clicked," he replied. "Ever since, I really got the confidence to just kind of fall in my groove of what I do."

Your Favorite Singer/Songwriter's Favorite Singer/Songwriter: Brittney Spencer

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Baltimore, Maryland's Brittney Spencer writes from a place of deeply ingrained spiritual inspirations, and her style is borne from years spent as a churchgoing Episcopal church choir member and musical arranger. 

Equally, it's inspired by having a friend introduce her to the music of the Chicks as a teenager. Just like the band whose 1998 song "Wide Open Spaces" is a crossover country classic, Spencer's music is cut from the same cloth.

On songs like the 2020 Compassion EP single "Sorrys Don't Work No More," lyrics like "I called you up in August, hoping I could be honest/But you never let me speak" hurt more than they rhyme—which is a rare talent. 

That skill is not only apparent in Spencer's forthcoming material, but in writers' rooms with the likes of a diverse slate of country performers including Allen, Maren MorrisBrandy Clark and Jason Isbell.

Overall, it's simply a case of if—and not when—Spencer's acclaim will grow.

The Country-Trap Iconoclast: Willie Jones

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No artist in the pop-country realm more uniquely highlights the diverse presentations allowed when welcoming more artists of color into the mainstream conversation than Shreveport, Louisiana's Willie Jones.

Suppose a Venn diagram space existed wherein early 2Pac's blend of earnestness and braggadocio blended with Kenny Chesney's desire to kick off his shoes and relax with a drink. In that case, the 26-year old singer-songwriter would occupy it.

From one side of his mouth emerges "American Dream," his critically-acclaimed 2021 civil rights anthem that includes the lyrics, "When you're livin' as a Black man/It's a different kinda American dream."

However, on the other side of the coin, you've got "Down By The Riverside," his Southern, countrified 2021 party track about corn, cotton and crawfish.

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A Brief History Of Black Country Music: 11 Important Tracks From DeFord Bailey, Kane Brown & More
Kane Brown performing at the 2023 iHeartRadio Music Festival in Las Vegas.

Photo: Denise Truscello/Getty Images for iHeartRadio

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A Brief History Of Black Country Music: 11 Important Tracks From DeFord Bailey, Kane Brown & More

While the world anticipates the arrival of Beyoncé's 'Act II: COWBOY CARTER' on March 29, revisit these 11 songs by influential Black country musicians throughout history, from a Charley Pride classic to a Mickey Guyton statement piece.

GRAMMYs/Mar 22, 2024 - 10:24 pm

In February, Beyoncé added to her record-breaking legacy by becoming the first Black woman to top Billboard's Hot Country Songs chart with her single "TEXAS HOLD 'EM."

"I feel honored," she shared on Instagram in a countdown post to her RENAISSANCE sequel, Act II: COWBOY CARTER, out March 29. "My hope is that years from now, the mention of an artist's race, as it relates to releasing genres of music, will be irrelevant."

Since she first dabbled in country music with "Daddy Lessons" in 2016, the icon has received consistent backlash about whether she belongs in the genre. That same year, audiences campaigned for a boycott against the Country Music Awards for her performance of the track alongside The Chicks, later resulting in its erasure from promotional advertisements. And eight years later, the conversation returns as radio listeners question if her music should air on country stations.

Ironically, if you look back through music history, you will quickly discover that Beyoncé isn't the first (and certainly not the last) Black musician doing country music. 

In fact, the genre plants its sonic roots in negro spirituals and field songs, written on slave plantations. African American Vernacular English continues to influence contemporary chart-topper's lyricism and vocal twang. The banjo, which descends from the West African akonting lute, remains one of the quintessential instruments of the genre. Whether Beyoncé or the many artists who came before her, nothing sits at the heart of country music more than Black art.

To understand the full scope of Black creatives' impact in country, GRAMMY.com examines some of the influential tracks and moments of those who have made their mark on the genre and the music industry — from DeFord Bailey's Grand Ole Opry debut in 1927, to Darius Rucker's post-Hootie & The Blowfish country foray in 2008, to Breland's 2021 fusion of country and hip-hop.

DeFord Bailey — "Pan American Blues" (1927)

Before there was Mickey Guyton, Darius Rucker, or even Charley Pride, there was DeFord Bailey, the "harmonica wizard" from Tennessee.

After performing locally, another musician introduced Bailey to Nashville powerhouse radio station WSM's manager, George D. Hay, who later invited him to join the Grand Ole Opry — making Bailey the first Black member. He quickly rose to become one of the program's highest-paid players at the time, largely thanks to his iconic instrumental tune, "Pan American Blues," which imitated the sounds he heard from the railroad during his childhood.

As of press time, the only other Black inductees in the Grand Ole Opry are Rucker and Pride.

Lead Belly — "In The Pines" (1944)

"My girl, my girl, don't lie to me/ Tell me, where did you sleep last night?/ In the pines, in the pines/ Whether the sun don't ever shine/ I would shiver the whole night through," Huddie "Lead Belly" Ledbetter questions in the Appalachian folk song, "In the Pines."

Though Lead Belly isn't the original writer of the song, his chilling vibrato on the recording inspired singers for years to come, including Kurt Cobain, who later covered the track in Nirvana's 1993 MTV Unplugged performance under the title "Where Did You Sleep Last Night?" and named the '40s country blues legend his "favorite performer."

Linda Martell — "Color Him Father" (1969)

In "Color Him Father," Linda Martell narrates the heartfelt tale of a stepdad who embraces his new paternal role to a widowed mother and her seven children. It's also the song that propelled her to stardom, landing her a historic performance as the first Black woman on the Grand Ole Opry stage and later opening the door for debut album, Color Me Country.

After the project was released, Martell stepped away from the limelight, but her impact lived on. She was the inspiration for contemporary luminaries like Mickey Guyton: "The fact that she was there was groundbreaking ... She gave me the courage to be here," Guyton told Rolling Stone in 2020.

Charley Pride — "Kiss an Angel Good Mornin'" (1971)

Through his nearly seven decades-spanning career, Charley Pride became a certified hitmaker and one of the most renowned pioneers of his time. By 1987, he amassed more than 50 Top 10 hits on Billboard's Hot Country Songs chart, with 30 peaking at No. 1 — including his most notable single, "Kiss an Angel Good Mornin'."

After Pride passed away from COVID-19 complications in 2020, the response to his death highlighted the magnitude of his legacy, receiving condolences from Dolly Parton, Billy Ray Cyrus, and perhaps the most personal from Darius Rucker.

"I couldn't have done what I do, I don't think, if there hadn't been Charley before me," Rucker said in an essay for Billboard. Pride served not only as an icon but also as a mentor to Rucker, and his kindness ultimately gave Rucker the courage to do the same for the next generation.

Cleve Francis — "You Do My Heart Good" (1992)

As a cardiologist and songwriter, Dr. Cleve Francis certainly knew a "good heart."

In his 1992 track, "You Do My Heart Good," Francis sings about a budding love that shows him how to see life in a beautiful light. The song eventually became the second single from his Liberty Records debut LP, Tourist in Paradise.

Francis later founded the now-defunct Black Country Music Association in 1995 to foster an inclusive environment in the Nashville music scene and provide resources to aspiring singers. Under his advisory, the BCMA, with the help of Warner Bros., produced From Where I Stand, a record book of Black artists' contributions to the genre.

Darius Rucker — "Don't Think I Don't Think About It" (2008)

Before 2008, many knew Darius Rucker better as Hootie, thanks to his remarkable '90s run as frontman of jangle pop band Hootie & the Blowfish. But with his second album as a solo act, 2008's Learn to Live, the world met Darius Rucker, the country artist.

Fittingly, he chose a heartbreaking ballad for his first country single — "Don't Think I Don't Think About It," a heartbreaking ballad about a man who wonders what could have been in a previous relationship. The choice resonated with country listeners:  "Don't Think I Don't Think About It" debuted at No. 1 on Billboard's Hot Country Songs chart, making Rucker the first Black country artist to have a chart-topper since Pride in 1983. 

Kane Brown — "Heaven" (2017)

Since his major label debut, Brown has possessed a unique boy-next-door charm, less "Western" than his peers. "Not laced up in a tight belt and buckle hat," but proof that "you can be who you want to be, and you can still listen to country music," his manager, Martha Earls, told Variety in 2018.

Take "Heaven," a romantic ballad with the Southern drawl and instrumentation of a classic country tune. But when you add Brown's R&B influence and natural swagger, the track invites audiences both in and outside of country.

Though Brown now has 12 No. 1 songs on the Country Airplay chart, "Heaven" is undoubtedly the country star's biggest song to date thanks to its crossover qualities and romantic resonance. And just last year, "Heaven" became only the seventh country artist in history to receive a diamond certification from the RIAA; Brown is the second Black country artist to achieve the feat, as Rucker's anthemic cover of "Wagon Wheel" reached diamond status in 2022.

Mickey Guyton — "Black Like Me" (2020)

In a 2020 interview with Rolling Stone, Mickey Guyton recalled that she wrote "Black Like Me" at a writer's retreat in 2019, thinking, "There is no way that anybody is going to accept this." But at the height of the Black Lives Matter protests after the murder of George Floyd in 2020, there was no doubt that it was what the industry, especially the country genre, needed to hear.

"It's a hard life on easy street/ Just white painted picket fences far as you can see/ If you think we live in the land of the free/ You should try to be Black like me," she croons on the chorus.

The single made Guyton the first-ever Black woman nominated for Best Country Solo Performance at the 2021 GRAMMYs, and also helped her earn nominations for New Female Artist Of The Year and New Artist Of The Year at the Academy of Country Music Awards and the Country Music Association Awards, respectively, in 2021..

Guyton continues to use her voice for advocacy, from speaking out on racial issues to chronicling the Black experience on her 2021 album, Remember Her Name

Breland — "Throw It Back" (2021)

Since making his debut with "My Truck" in 2019, Breland has been praised for his innovative fusion of country, gospel, hip-hop, and R&B. But beyond his sonic landscape, he's also inviting some unlikely choreography into the genre: twerking.

"If she got a shot of whiskey, she know how to throw it back/ She turn up for Elvis Presley, told the DJ, 'Throw it back,'" Breland cheers in the chorus of the trap-infused track.  "If you sexy and you know it, make it clap."

"Throw It Back" features Keith Urban, whoappreciates Breland for his confidence to go beyond the mold of country music's expectations. "He's one of the only artists I've ever met that does not care at all what something sounds like or what box it fits. If he likes it, if it catches his ear, he wants to be a part of it in some way," Urban explained to Taste of Country in 2021.

The War and Treaty — "Blank Page" (2022)

The War and Treaty are making the most of their "Blank Page."

The husband-and-wife pair — Michael Trotter Jr. and Tanya Trotter — began their musical journey together in 2016.  Seven years later, thanks to their first major label EP, 2022's Blank Page, they also started making history. The War and Treaty became the first Black duo to receive a nomination for Duo Of The Year at the 2023 Academy of Country Music Awards, where they also delivered a stirring performance of the EP's title track, a heartfelt song about a new slate in love. 

Six months later, they made history again as the first Black pair nominated for Duo Of The Year at the 2023 Country Music Association Awards; they took the stage there as well, performing"That's How Love Is Made" from their 2023 album, Lover's Game

They added to their growing legacy at the 2024 GRAMMYs as well,  receiving their first GRAMMY nominations. "Blank Page" earned the duo a nod for Best American Roots Song, and they also were up for the coveted Best New Artist.

Tanner Adell — "Buckle Bunny" (2023)

When Beyoncé dropped "TEXAS HOLD 'EM" and "16 CARRIAGES" in February, country newcomer Tanner Adell readily tossed her cowgirl hat into the ring to become Queen Bey's next collaborator. "I hope Bey decides to sprinkle me with a dash of her magic," she pitched in a tweet that has now garnered more than four million views.

Adell's music is reminiscent of Beyoncé's own empowered narratives, particularly the 2023 single "Buckle Bunny," which even declares that she's "Lookin' like Beyoncé with a lasso." Like Breland, Adell brings a hip-hop flair to country music, exemplified by the thumping beats and rap-inspired singing of "Buckle Bunny."

As artists like Adell, Breland, Kane Brown, and more continue to push the boundaries of the country genre, they'll also remind listeners of its rich lineage in Black culture — past, present, and future.

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Everything We Know About Beyoncé's New Album, 'Cowboy Carter': Two New Singles, Tracklist, A Shift To Country & More
Beyoncé at the 2024 GRAMMYs.

Photo: Kevin Mazur/Getty Images for The Recording Academy 

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Everything We Know About Beyoncé's New Album, 'Cowboy Carter': Two New Singles, Tracklist, A Shift To Country & More

Beyoncé released two new singles and announced a forthcoming new album after teasing the new music during a Verizon 5G commercial during the 2024 Super Bowl. Here's everything we know about the 'Cowboy Carter' album dropping March 29.

GRAMMYs/Feb 12, 2024 - 05:23 am

Editor's Note: This article was updated on March 12, 2024 with details about the album title and again on March 19, 2024 with more information about the album.

"OK, they ready: drop the new music." With those seven words, Beyoncé announced new music during a commercial for Verizon 5G during the 2024 Super Bowl.

As the Beyhive clamored frantically to discover what, exactly, their queen was teasing, the answer soon became clear as the superstar unveiled two new tracks titled "TEXAS HOLD 'EM" and "16 CARRIAGES."

But that's not all! The two new songs not only follow Beyoncé's seventh album, Renaissance, and her mega-successful concert tour of the same name, but also build on the single "MY HOUSE" from last year. The dual ditties appear to be components of a larger project, potentially marking the next phase of Beyoncé's ongoing Renaissance.

Below, GRAMMY.com rounded up everything there is to know about Queen Bey's surprise drop and what cards she may have up her sleeve.

Beyoncé's Long-Awaited Country Era Is Upon Us

While Beyonce's Super Bowl LVIII commercial paid homage to 2016's Lemonade, introduced the world to the possibilities of "Beyonc-AI" and even sent her to space, the surprise singles signal a new direction for the living legend into bonafide country territory. 

"TEXAS HOLD 'EM" is a twangy, two-stepping joint addictively tailor-made for a night of line dancing and lassoing, with Bey singing, "This ain't Texas, ain't no hold 'em/ So lay your cards down, down, down, down/ So park your Lexus and throw your keys up/ Stick around, 'round, 'round, 'round, round" before she flirts, "And I'll be damned if I can't slow dance with you/ Come pour some sugar on me honey, too/ It's a real live boogie and a real live hoe-down/ Don’t be a b—, come take it to the floor now."

Meanwhile, "16 CARRIAGES" balances out the yee-haw groove of its jauntier sibling by turning out a slow-burning power ballad as Bey spins a tale of lost innocence and grinding away in the name of a better life. "Sixteen carriages drivin' away while I/ Watch them ride with my dreams away to the/ Summer sunset on a holy night on a/ Lone back road, all the/ Tears I fight," she rhapsodizes over sparse acoustic guitar before slide guitar and pounding percussion crash over her gentle vocals like a wave.

The Tracklist Has Been Announced

On March 27, Beyoncé teased the 'Cowboy Carter' tracklist on Instagram, two days before its release. The post revealed a "Jolene" cover with Dolly Parton, a collaboration with Willie Nelson, and hinted at a partnership with Linda Martell, the first Black female country artist to perform at the Grand Ole Opry, through the track "The Linda Martell Show."

It's Already Shattering Expectations And Making Chart History

In an Instagram post marking the 10-day countdown 'til Cowboy Carter, Beyoncé expressed gratitude and gave deeper insights into her album's journey, a sequel to RENAISSANCE. She reflected on how navigating the criticism and resistance surrounding her foray into country music fueled her evolution as an artist and fortified her resolve to transcend constraints placed on her creative expression.

"I feel honored to be the first Black woman with the number one single on the Hot Country Songs chart. That would not have happened without the outpouring of support from each and every one of you," Beyoncé wrote. "My hope is that years from now, the mention of an artist’s race, as it relates to releasing genres of music, will be irrelevant."

It All Started With A Super Bowl Ad

Beyoncé started all this ruckus with an epic Super Bowl commercial for Verizon. The ad began with the two-time halftime show headliner filming a music video for her 2023 one-off "My House." Clad in a red sequined ensemble and surrounded by faceless backup dancers in the same shade of scarlet, Bey bursts from a giant house (also red) as she pronounces, "Who they came to see? Me! Who rep like me, don't make me get up out of my seat. OK!"

From there, Beyoncé hatches a plan with Tony Hale to break both the internet and the service provider's 5G with a number of viral stunts — including starting her own "Hold Up"-inspired lemonade stand (baseball bat and yellow gown included), climbing to the top the Sphere in Las Vegas, starring in a Bey-ified Barbie redux titled "Bar-Bey"and announcing her uncontested run as "Beyoncé of the United States." You've got our vote, BOTUS!

This One's For The "Daddy Lessons" Fans

Of course, it's a known fact that Beyoncé can sing, well, literally anything, but the sonic shift is particularly gratifying for fans of her zydeco-tinged cut "Daddy Lessons" from 2016 or the even more countrified version she recorded with Dixie Chicks after performing the Lemonade fan-favorite with the group at the 2016 CMA Awards.

Beyoncé Cowboy Carter Art

The Songs Herald The Arrival Of Act II: Cowboy Carter

The two tracks aren't just a one-off, either. The landing page of Beyoncé's official website updated once the songs were released into the world, promising, "act ii…3.29." The promise of a second act refers to the megastar's GRAMMY-winning album Renaissance, which has been billed as "Act I" since its release in the summer of 2022. 

Many fans suspected a full visual album might be the second act of the house-inspired era, but it appears that much like Beyoncé herself, the Renaissance won't be limited to a single genre.

Could Visuals (Finally) Be On Their Way?

Along with the pair of singles, Beyoncé dropped a teaser for "TEXAS HOLD 'EM" on social media. In the clip, the superstar drives an old-fashioned yellow taxi with a Texas license plate reading "HOLD EM." Opting not to write a caption, the post left the Beyhive buzzing at the possibility that a visual component might accompany Cowboy Carter in some form or another. Though given that fans are still eagerly waiting for any sign of OG Renaissance visuals, don't hold us (or Queen Bey) to this hypothesis.

On a completely unrelated and entirely speculative note, the last time Beyoncé was spotted driving a bright yellow vehicle through the desert, it was the same one Uma Thurman drove in "Kill Bill" for the iconic "Telephone" music video with Lady Gaga. Take that tidbit from the P—y Wagon for what you will, Honey Bee…

The Clues Were In Plain Sight At The GRAMMYs

*Beyoncé at the 2024 GRAMMYs in a western-inspired custom Louis Vuitton look.* (Photo: Kevin Mazur/Getty Images for The Recording Academy)

Turns out Beyoncé's been dropping hints for a while! At the 2024 GRAMMYs, the superstar wore a western-inspired outfit — a variation of the closing look from the fall 2024 Louis Vuitton menswear collection —  to support her husband Jay-Z, who was awarded with this year's Dr. Dre Global Impact Award. During his off-the-cuff speech, the Roc Nation mogul recognized his wife's success as the most-awarded artist in GRAMMY history while having yet to win Album Of The Year as Bey looked on from underneath her spotless white cowboy hat. We should've known!

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Remembering Toby Keith: 5 Essential Songs From The Patriotic Cowboy And Country Music Icon
Toby Keith performs at the 2021 iHeartCountry Festival in Austin, Texas.

Photo: Michael Hickey/Getty Images

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Remembering Toby Keith: 5 Essential Songs From The Patriotic Cowboy And Country Music Icon

After a two-year battle with stomach cancer, country star Toby Keith passed away on Feb. 5 at the age of 62. Revisit his influence with five of his seminal tracks, including his debut hit "Should've Been a Cowboy."

GRAMMYs/Feb 7, 2024 - 04:39 pm

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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Charles Esten On How Procrastination, Serendipity And "Nashville" Resulted In 'Love Ain't Pretty'
Charles Esten

Photo: Kirsten Balani

interview

Charles Esten On How Procrastination, Serendipity And "Nashville" Resulted In 'Love Ain't Pretty'

For the first time in his career, Charles Esten is fully focused on music. But as the actor/singer details, his debut album, 'Love Ain't Pretty' is much more than another venture — it's a lifelong goal achieved.

GRAMMYs/Jan 3, 2024 - 10:40 pm

Like many of his peers, Charles Esten has known music is his calling since he was a kid. But at 58, he's just now getting the opportunity to do what his contemporaries are long past: release a debut album.

As fans of the beloved ABC/CMT series "Nashville" or the hit Netflix drama "Outer Banks" know, Esten first established himself in the acting world. But as his "Nashville" role revealed, the actor also had some strong singing chops, too — and it wasn't a coincidence.

Due Jan. 26, Love Ain't Pretty is a testament to both Esten's patience and his passion. Combining his soulful country sound and emotive songwriting, Love Ain't Pretty poignantly captures his years of loving and learning. And with a co-writing credit on all 14 tracks, the album is the purest representation of his artistry possible.

"Being the age I am, and the difference of what this album is to what maybe my first album would've been if I was 28, is the intentionality," he tells GRAMMY.com. "I can chase what's thoroughly me, and the facets of that. And in the end, that, I think, makes better music anyway."

As the title suggests, Love Ain't Pretty mostly focuses on finding the beauty in life. Along with several odes to his wife, Patty ("One Good Move," "Candlelight"), Esten delivers tales of self-reflection ("A Little Right Now") and simply enjoying the moment ("Willing To Try"), all with a grit that's equal parts inspiring and charming.

Perhaps the most fitting sentiment on the album is "Make You Happy" — not because of its lovestruck narrative, but because it captures Esten's goal with Love Ain't Pretty and beyond: "Wanna make you happy/ Wanna make you smile."

"I know that musical superstardom is not an option," he acknowledges. "I don't even seek it. So, what do I seek instead of perfection? Connection."

Below, Esten recounts his fateful journey to Love Ain't Pretty — from his first taste of stardom to finally fulfilling his lifelong dream.

This interview has been edited for clarity.

All the way back in third grade, our elementary school had a contest to write the school song. They said, "Find a Disney song and use the melody and then put new words to it." I did it to "It's a Small World." I probably wrote little doodles on my own [before that], but that was the first one with any bit of fame. 

I went back, like 10 years later, and they were singing that. They actually made it as part of all the assemblies and everything. That feeling, to hear people singing words that you thought of, I'm sure that was the beginning of this path.

Eventually, when I went to college, I was in a band. But, even before I was in a band, my grandmother passed in my sophomore year of college. And, I didn't get back in time to see her. She had helped raise me when I was little, after my parents' divorce, so it hit me hard. I somehow was able to put what she meant to me in a song, and that made a big impact in a lot of ways. Whereas that third grade little ditty made everybody laugh and smile and everything, this made my mother and my aunts and uncles [cry] in a warm, loving way. I could see it affecting them. 

I could [also] feel it help me process what I was going through. That was another bit of an aha moment, like, "Oh wow, writing a song can do that also."

Right after that, I started a band. That experience of hearing a band bring your song alive — it was so much more full, this experience, and hearing somebody else add a thing you hadn't thought of, that was another true revelation, the power of that. So I got hooked rather quickly. 

Honestly, I probably would've stayed in that world if my band had stayed in that world. They all made the decision to graduate and go be doctors and lawyers and stuff, as the song says. When that finished up, I didn't know what I was going to do next. But, having experienced that made it clear to me that I was not cut out for a desk job — even though I had an economics degree. 

I had some friends that had gone to L.A. and started becoming actors. I thought, "Maybe I'll give that a try." But the long and the short of it is, if you had asked me, "Will you continue in music?" I'd be like, "Absolutely. I'm going to go out there and I'm going to meet another bass player and a drummer and another band will come."

It didn't happen. I went to London and played Buddy Holly for two and a half years in the musical "Buddy." When I went back to L.A. after that, then the family started to come, and so the band just never happened. But I had a piano, had guitars — I never stopped writing or playing.

At one point, I had the thought, "Well, I might have missed the boat in terms of ever getting to be a performer myself, but I can write songs." And by this point, I was really listening to a whole lot of country, '90s country, 2000s and all.

So, I decided I was going to start writing in a more formalized way, in a more intentional way, instead of just whenever a song came to me. And, as soon as I sort of said that, things started happening.

I met my friend Jane Bach, who is a great Nashville songwriter. She was going back and forth between LA and Nashville at the time. She invited me to sing at the Bluebird [Cafe in Nashville], which I knew very well, and I said yes. And twice, I had to cancel because I got other work. And at a certain point, I literally said to my wife, "When am I going to get to go to Nashville? That'll never happen."

[That] maybe was two or three years before "Nashville." And then I get this script that says, "Nashville." Next thing I know, I'm here and I'm literally doing my first scene in the Bluebird.

I understand, very cleanly, that ["Nashville"] opened all these side doors that most people don't have access to. But, I also know that there's a chance they could have all been opened and I could not have been ready. 

When it finally [happened], for a lot of people, just looking at an actor who's playing a singer/songwriter, I get the feeling that it was a pleasant surprise — I like to think that there was a little more there than they expected. It was actually more authentically who I was than the actor.

I never really quite verbalized this, but the feeling [of landing "Nashville"] was one of — it'll make me emotional — completion. I felt like the show was an answer to so many unsolved things in my life. And that's, I think, why we haven't left. And it's also why the album meant so much to me.

It meant so much to me that I didn't just get here and do an album. I got here at 46. To be that old and not really know who you are as an artist — I never had to define myself. So, I didn't chase that immediately. I just wanted to make music in Music City and make as much as I could. 

I always felt behind, because all my contemporaries that had been here, very many of them were already incredibly famous and already had done so much. But you can't [focus on] the road not taken. 

I have to admit, there's some part of me that would be like, "What if you were putting out your first album at 28?" That's nothing I sort of worry about. I know that it wouldn't have been this. I wouldn't change anything. I have this wife and this family and this career that brought me here. It feels like this was the way it was meant to happen, as strange as it all is.

I felt more prepared than people might expect. And I had something that most people didn't have, which was, Deacon walked in places before I did. Deacon sang at the Bluebird before Charles did. Deacon was at the Grand Ole Opry before I was.

That began what I would call my 10,000 hours in this town. Between the number of hours I've been able to be on stage at these incredible venues, and play music with these incredible people, and all the singles I was able to put out over the last 10 years, I now feel like that, in some ways, I have as much of a catalog as people that have been here for those 30 years. But, it's still my first album, which I've held onto for something special, and I'm so grateful for the way it turned out. I couldn't be happier.

I knew that I wasn't emptying the whole toolbox to play Deacon. But, having said that, I'm so moved by how much playing that guy influenced my music and my songwriting. A song like "A Little Right Now," it roars at the top and rages a little bit, but in general, that is a Deacon song through and through. "I'm a farmer praying for rain/ I'm a gambler that needs an ace of spades/ I'm a sailor hoping for a gust of wind/ I'm a singer looking for that song/ I'm a prisoner that ain't got long/ I'm a dreamer waiting for my ship to come in/ But lately all my roads have been running out/ There ain't no silver linings in these clouds/ Help me, Lord, and show me how to find the kind of faith that I once found/ 'Cause I could sure use a little right now." When you watch the show, you'll go, "That's the Deacon-est thing I've ever heard."

There's other songs on this album as well. "Maybe I'm Alright" — Deacon's journey was from utterly broken to "maybe I'm alright." As I look at it, he informs this album.

I'm a procrastinator. That's why I released so many singles in 2016, that world record. [Editor's note: Esten released 54 original songs once a week for 54 straight weeks, earning a Guinness World Records title in 2018 for the "Most consecutive weeks to release an original digital single by a music act."] 

That was a mind hack — a life hack — to arbitrarily create deadlines. And, my God, did that work, because I just started putting it out. [After that,] I started thinking about an album, and I even made an early attempt at it, and then COVID hit. 

They felt like songs from a thousand years ago [after the lockdown]. I pretty much scrapped it and didn't use any of them, and said, "I've just got to do this again in a different way. It's a different me. It's a different world."

My wife is not a procrastinator. And I'll show her, sometimes there's an upside of procrastinating. It's like using a crockpot when there's a microwave right there — it stews in all the ingredients. 

Deacon's a major ingredient, but if you just put that major ingredient on it and cook it real quick, it's too pronounced. Stew it in there with all the other ones until it's a new flavor, a new thing in its entirety. And that's what happened.

It's also interesting that, being the age I am, and the difference of what this album was to what, maybe, my first album would've been if I was 28, is the intentionality in terms of radio success or chart success — or chasing something that might not be thoroughly you, but might be a little more popular than thoroughly you. There's no reason for it at my age, so I can chase what's thoroughly me, and the facets of that. And in the end, that, I think, makes better music anyway.

There's a video I put out for "Somewhere in the Sunshine." Already, the impact of that song is sort of blowing my mind. The video is full of quotes from people that commented on YouTube about who they lost, and how it's giving them a little moment of peace, and how it's blessing them. That's my radio play. That's my GRAMMY.

I try to always realize how blessed I am to be able to do this. It's so much more precious later in life. I think people sometimes meet me and I have an enthusiasm for it that is younger than my years. And, maybe [that's] just because I've been waiting at a distance so long and it finally came true. I might get jaded someday, but it hasn't happened yet.

There's still an outsider mentality. I also feel like an anomaly. All the great artist friends I have, I'm not like them. They've been on the radio, they've had cuts, they've had hits. And then, all the new ones starting off doing their first album, I'm not in their group either — they have a whole career and future ahead.

On the other hand, I feel warm and welcomed in all of those arenas, and in everyone in this town. It always has been unusual for me here. All the reasons I'm here, all the why's, all the how's — but I guess, in the end, that's how I fit, and that's how I belong.

I was blessed that I was able to take my time. I think, once you let go of the outcome, freedom is available. It's just really hard to let go of that outcome. But, as I said, I'm a different beast. What I am means I better let go of that outcome, because the odds of me getting a No. 1 smash off this, they're not great. But the odds of me moving somebody with this music? I think they're pretty good.

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