Aaron Watson

It’s a frigid, gloomy Saturday morning in Houston. Mist hangs over the damp track grounds of the Sam Houston Race Park, where tonight Texas country singer-songwriter Aaron Watson is scheduled to take the stage. A crew works on constructing the stage for the evening’s headline act. Jockeys trot their derby horses around muddied red dirt for a warm-up.

“It’s a neat place, isn’t it?” Watson says as he takes in the view from behind a round table in the luxury suite section of the venue.

But this big-ticket setting is not what drives him. No matter how significant top billing is to his career status, tonight’s performance is going to be like every other he’s given throughout his career — he’ll be playing his heart out for his devoted fans and, most important, his family.

A Yeti tumbler of black coffee, a navy blue T-shirt, worn blue jeans, a signature charcoal-and-black Vaquero album logo baseball cap over his dark crew-cut hair, and a pair of tan square-toe Tony Lamas that have a hint of cow manure on their well-worn leather: It’s a style that skirts the line between distinguishable cowboy and seasoned country artist on tour. Watson’s demeanor? He certainly seems geared up for an exciting night onstage, but also laid-back and comfortable in his own skin.

The singer is in a good place after years of career and creative struggles, the kind that build character and lead any thoughtful artist down roads of self-discovery. At certain points, after discouragements and unsatisfactory breaks, he’s been ready to hang up his Stetson for good.

“In my very early stages, I had the opportunity to meet with some record labels,” Watson says. “They flew me up to Nashville and they were very interested in me as an artist, but once I got up there I realized that they were more about changing me into something they wanted, rather than making me the best version of me. ... I think in the beginning, I took that as some serious rejection. [And then] I had the president of one of the largest record labels in the world tell me that I’m not a star and I would never be a star, but that if I continued to work on my songwriting maybe I could write a song for a star. [It] kind of sent me packing, kind of crushed me.”

Watson credits his father, Ken, a disabled Vietnam veteran and former custodian, for putting him back in the game mentally.

“A few days later, I was at home in Amarillo, and I was drinking coffee with my dad at the kitchen table. He said, ‘So how did the meetings go in Nashville?’ And I said, ‘Well, they didn’t go real good. ... And I remember Dad said, ‘Well, that’s all right. That’s what those idiots said to Willie Nelson for all those years.’ And I was like, yeah. ... And then Dad said, ‘You know Willie finally really made it big-time when he was about 45.’ And I was like, whoa. ... I said, ‘Dad, are you telling me I’m gonna have to grind it out for the next 20 years if I’m gonna make it?’ And I remember he took a sip of coffee and kind of had this little grimace of a grin and he said, ‘Yeah, if you want it bad enough.’

“Looking back, I realized that [the rejection] was a very pivotal moment in my career where I stood up for who I am and my brand of music, and that really set me on this path, this path of independence,” Watson says.

Watson has since stepped out and developed his own company, cleverly dubbed Big Label Records, to distribute his music. It was a big step for a guy who’d worked dance halls and released countless local hits. He’s now amassed more than a dozen releases in the last two decades and has enough songs under his well-polished Rodeo Houston belt buckle to last a lifetime.

Born in Amarillo, Watson first displayed his love of singing with his supportive parents, Ken and Andra, at their local Church of Christ. His focus on music intensified after a back injury forced him to give up his aspirations of becoming a professional baseball player and enroll at Abilene Christian University. At age 18, he purchased his first guitar at a pawnshop with money he earned mowing lawns.

“I remember that very first moment when we recorded our first little demo, then we got done with it, and they had burned the song on a CD,” Watson says. “I put it in my truck and I got to listen to it all the way home, just hearing my voice sing words that I wrote, with a fiddle, a steel guitar, and a band behind me. I’ll never forget that feeling. ... I was driving on Judge Ely Boulevard in Abilene, Texas, and it was a little dream come true.

“And I think for me along the way it’s just been little dreams, little dreams coming true. It’s never been about, ‘Have I made it yet?’ It’s just reaching or achieving those little goals that I set before myself.”

A couple of decades’ worth of little goals later, his 13th album, Vaquero — the highly anticipated follow-up to his critically acclaimed The Underdog record — debuted at No. 2 on the Billboard Top Country Albums chart. “Outta Style,” its first single, quickly climbed the country rankings, earning Watson his first Billboard Top 10 single.

“It literally took us 20 years to get our first Top 10, and it’s funny that [‘Outta Style’] was the one that was a hit because I probably wrote it in three minutes. But I just wrote my story. That song is the story of my life, my music, and the relationship with my wife,” Watson says.

“I enjoy playing shows, but I think where I’m living life is when I’m at home with my wife and my babies. I kind of just exist on the road. I know that sounds kind of sad, but it’s not where my heart is. So, it’s like I’m excited about today because ... after the show tonight, I get to go home.”

Home nowadays is on a lush, open piece of land in Buffalo Gap, Texas, where Watson, wife Kimberly, and their three kids, Jolee Kate, Jack, and Jake, spend their free time lounging at the pool, playing catch in the yard, and visiting their neighbors across the way at the Perini Ranch, home of famed cowboy cook Tom Perini.

As is the case with any traveling troubadour, though, Watson’s restorative home days are a rarity. High-profile gigs and public appearances such as the CMA Awards have kept him from spending much time soaking up the sun. He’s working harder than ever. His first live album in nearly a decade, Live at the World’s Biggest Rodeo Show, was recorded on the opening night of the 2017 Rodeo Houston and released in August 2018, one year after Hurricane Harvey made landfall in Texas, with a portion of its proceeds going to the Rebuild Texas Fund. Then there was the October 2018 release of his holiday album, An Aaron Watson Family Christmas. And he’s been writing and recording for his next studio album.

Though his schedule is a struggle at times, when it comes to writing songs, his mind often returns to the happiest places in his life. A recent single, “Run Wild Horses,” is a romantic ode to his wife, and each of his children also have songs dedicated to them.

Until his journey home to gain inspiration, Watson is focused on tonight’s performance. And when the sun finally comes out of hiding, while the winning jockey is celebrating, Watson will trade out his casual look for his signature black felt cowboy hat, a classy long-sleeve pale rose button-down, and his custom “Three Wooden Crosses” acoustic guitar. When he steps onstage, as he does no matter the state, venue, or set list, he’ll hook listeners with his contagious energy and humble persona, expanding an ever-growing fan base.

“I’m very excited about my career. I feel like I’m just getting started,” Watson says. “We still go places and they call me up-and-coming and I kind of love that. ... We’ve been doing it for a long time. And to be this far in my career and people think that we’re just getting started, man, that’s really cool.

“We’re not up-and-coming. We’re just slow and steady.”

What's Up With Watson?

What is something your fans might not know about you? — My first love was baseball.
Favorite team: — I saw Nolan Ryan’s fifth no-hitter September 26, 1981. I grew up loving the [Houston] Astros but then when Nolan went to the [Texas] Rangers, I started loving those Rangers. And now ... I know some of the boys on the Astros. I love both those teams. I love the fact that I take my kids to those teams. Great role models.
Favorite place in the West:  — Home: Buffalo Gap, Texas
First song you look for on a jukebox:  — “The Way I Am” by Merle Haggard
What is a staple in your wardrobe? — Well, boots [Tony Lamas] and I’ve got my Rodeo Houston buckle, but my staple is to never have a staple.
If you weren’t a singer you would be ... — A songwriter.
What other artists would you recommend that your fans would love? — It’s funny about a lot of my heroes: the younger generation is not familiar with them. So anytime I can tell kids about Townes Van Zandt, Guy Clark, Rodney Crowell, those legendary songwriters, those are the ones that I love.
A band that’s been on repeat: — There’s this one band I’ve been listening to and they’re out of San Marcos, Texas, called The Oh Hellos.
Favorite Western word: — Y’all.
Favorite western book or movie: — I love All the Pretty Horses.

Visit cowboysindians.com to listen to an Apple Music playlist that spans Watson’s entire career. Find out more about the artist at aaronwatson.com.

Photography: (lead image) Joseph Llanes/courtesy monarch publicity, CK dirks photography/courtesy monarch publicity.

From the January 2019 issue.