As we continue to celebrate 20-year anniversaries of great albums from 1999, one can't help but reflect how different the music industry is today.

For instance, instead of purchasing a physical copy of an album from your go-to music chain, nowadays audiences primarily consume music via streaming services like Spotify or Apple Music. And if they want to hear something new, they simply turn to computer-generated algorithms that can recommend what you might like based on what you've already listened to. Artists, meanwhile, can simply upload their music straight to streaming services, effectively cutting out industry gatekeepers and middlemen who once offered exclusive access to distribution.  

But just because it's easier to hear and share music with the world in 2019, that doesn't mean it's become simpler to write a great song or keep people's attention.

That's where A&R—which stands for "artists and repertoire"—is still highly relevant. An A&R team's goal is to not only bring in the talent to a label or publisher, but to also help the artist develop their sound, find new collaborators and make sure they have all the tools and support they need to continue to succeed.

We spoke with seven women working in A&R-related roles across labels and other music organizations to learn about what A&R looks like in 2019, creating safe, fairer spaces for women in the music industry, helping artists capture audiences' ever-waning attention, and why, even with streaming dominating the industry, their jobs are more important than ever.

Artists Matter, And A&R Does Too

One thing is clear: With an abundance of choice comes the danger of oversaturation. When A&R professionals step in, they help artists navigate details of the industry and make sure their voices cut through the noise.

As Latoya Lee, VP of Creative Services at Atlas Music Publishing (which has offices in the musical hotspots of New York, Los Angeles, Nashville and Atlanta) puts it: "More so than ever the market is very oversaturated, and I think we're in this space where everyone thinks they're well equipped for everyone's job and that's not the case… most of the time it's the team behind that person that really helps you stand out."

Meanwhile, Taylor Lindsey, VP of A&R at Sony Music Nashville, explains how the shift in country music, where more now performers are also songwriters, has moved the focus of their work to encourage more creative collabs. "I think that where before A&R was really just about finding songs and giving them to artists now it's more of an opportunity for us to help go 'okay, here's a writer that you haven't thought to write with yet. We need to get you in a room with them,'" she said.

Stephanie Wright, who also works in country music as the VP of A&R at Universal Music Group Nashville, made the same point about the shifts in country. She added that A&R "is a different process for a new artist or one that is three or four albums in, then it's more about how they're staying relevant."

Gelareh Rouzbehani, CEO of Rouz Group, an A&R and artist management company she founded in Los Angeles after her time working on the label side, speaks to the vital role of A&R within the greater structure of a label. "I think A&R is the nucleus of the record label; without the right song, the right music, you don't really have a product to push, and other departments can't do their work. I think it always starts with the music... and then from there we build on."

Allison Jones, SVP of A&R at Big Machine Label Group, another major Nashville label, echoed this. "A&R is the funnel through which music gets sent whether it be to a record label or a publishing company or to an artist directly. The term artist and repertoire means the artist and the repertoire of songs that they sing. So as long as there's music there has to be someone that is going to make sure it gets funneled to the right place."

She continued, highlighting that even as the digital music era makes music discovery easier, it is still important to have an A&R team focused on finding the gold. "I think now more than ever it's really key to have that front line of A&R that's scouring all those [music and social media] platforms, in addition to the good old fashion meetings and the good old fashion going to shows and showcases," Jones added.

Data Helps, But It Can Only Reveal So Much

Speaking of the digital music age, sometimes when an artist's streaming accolades are shared, it can sound like someone reading random numbers off a spreadsheet. But with some context, streaming numbers and other data can show us a lot and help an artist and their team test out what resonates with listeners and what doesn't. As several women pointed out, streaming numbers come from real people listening to your music, which is, of course, important to pay attention to.

Everyone seems to agree that while looking at various data points available across streaming and social platforms can help an artist and their team make more informed decisions, it is important to take it with grain of salt and balance it with the irreplaceable gut instinct. Barbara Sealy, who is the Managing Partner at SB Music Management in Los Angeles, pointed to exactly that.

"Data is hugely helpful but it could also be a hindrance. Data can tell you what's popular now, but not necessarily tell you what's good and that's where you have to have go along on gut instincts. I have to really take that data and know how to break it down, but also know how to balance it," Sealy says.

She points to different ways you can look at data, like comparing streaming numbers for songs before and after an artist tours and to dig into website data to see where people are listening to their music, as they should be touring there.

Quality Always Matters

While the current musical landscape may make it easier for artists to share music and potentially snag a blip of listeners' attention with a viral moment, as Wright points to, they still need to be ready for this moment, and to have what it takes to keep their attention. "Attention comes quicker; streaming gets your music out and exposure can come fast, but they may not have been prepared for it."

She added that as someone working in A&R, "With the vast amount of music that is out there now, I think it's going to become important, as far as A&R goes, to really suss out what things are authentic and have that true artistry about them, that will have lasting power."

Wright continued, "You want to invest in the long haul…[to ask yourself] how do you get the consumer the authentic things that they're going to want to follow and to continue stay engaged with?"

Rouzbehani underscored the power of quality music. "I think music is cyclical, and it comes in waves. I'm a firm believer that great artists and quality products will always win in the end. I hope that we continue to work toward elevating those that are actually putting out amazing bodies of work," she said.

Sealy echoed this as she talked about the difficulty she has seen some of her artists face that don't fit neatly into genre boxes. Even though it may take time, she firmly believes that in the end, quality music will always see its time of day. "When good music comes out, everybody will absolutely support it. And we've seen that time and time again," she said.

A&R Is Still About Opening Doors...

Ashley Calhoun, VP of A&R at Pulse Media in Los Angeles, spoke to the importance of opening the door for others to help continue to create a more equal playing field across the music industry.

"I think everyone who's in a position and who has the ear to the executives and consultants that make those decisions should speak up. I think that's super important because if we don't say anything about it, nothing's going to change," Calhoun explained.

She continued, emphasizing the importance of practicing what you preach. "We just really have to have each other's backs because if we don't, we can't expect men or someone else to. Even though there's a lot of great men that really support this vision, we have to just be proactive."

…To Keep Moving The Music Industry To Be More Inclusive & Fair

Lindsey said that while she is proud of the many female artists on Sony Nashville, she and her colleagues recognize that representation in country music is an issue. "It's definitely something that we're paying attention to and we are pushing harder and we are pushing back at because there are female artists in town that deserve to be here."

She added to this point; "I would really love to see more diversity especially in country music…There are so many great artists out there that really kind of don't necessarily fall into a genre. They have country sensibilities or they might have some pop melodies, or they have pop sensibilities and country lyrics…So because of those things I think that it would be really great just to see country open up a little bit more and have more diversification."

Lindsey also stressed the importance of the music industry as a whole coming to a decision as to "what the fair and just compensation needs to be for songwriters and artists across the board," an important point which came up in all of the conversations.

Lee shared her biggest hope for the industry is to see "more black women in positions to make decisions." She continued, underscoring what she sees as her role to help make this happen.

"And A&R more so than anything, because we have lots of women in marketing and lots of women in promotions and radio, and we have lot of women in publicity and those positions, but we don't have enough black women in A&R. That is very important to me, because that's going to be the defining moment in my career, being able to say that I molded the next generation of young women music executives, but also young black women executives."

Like Lee, each woman we spoke with clearly saw a key part of their role in A&R as not only opening doors for the artists they work with, but for other women looking to get their foot in the door on the other side of the music industry. They all spoke of who helped champion them to get their start in the industry, with several pointing out they didn't have female mentors to work with or look up to on their teams. This is why they see female to female mentorship as another important part of their career.

The Importance Of Female Mentorship

Sealy emphasized the importance of making the time for other women, even if it's just a few minutes to answer a few questions. "We all need to be talking to each other…And mentoring is really, really important…We really need, as women, to stop and make a little bit of time for that next girl coming up. Even if we've kind of got to the top of where we are, we need to ensure opportunities are there for others, and especially create an opportunity to be that woman mentor."

Each of the women echoed the importance of mentorship and dialogue in some way during our conversations. Rouzbehani eloquently summarized the importance of empowerment and encouragement.

"I think it's so powerful when women come together," she said. "We've seen it happen time and time again in history, and in the industry now we're seeing more of it, and it's really making an impact. Younger girls, whether they're on social media or they see if from afar, they're a part of this, I think are influenced and inspired by that."

Jain On How Coachella Helps International Artists, Honoring Miriam Makeba's Legacy & 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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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.

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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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