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‘Sad-Cowboy Songs’ Made Ryan Bingham an Oscar Winner. Now He’s Singing About Love

‘Sad-Cowboy Songs’ Made Ryan Bingham an Oscar Winner. Now He’s Singing About Love

“I’ve always been afraid of losing that human connection with fans,” Ryan Bingham tells me. We’re holed up in the green room at Cain’s Ballroom in Tulsa, Oklahoma, where he is preparing for the second of back-to-back nights headlining the historic honky-tonk. “If I don’t really believe or feel what I’m singing about, how do I expect them to feel anything?”

Bingham has been thinking a lot about his fans these days. How crowds show up early in an artist’s career out of curiosity, and then, through a combination of good songwriting and engaging stage presence, start to return time and again.

“Over the years, people coming and wanting to hear those songs and share their story of why it’s important to them reminds me that ‘I’m out here for you guys,’” Bingham says.

Few art forms are as intertwined with the chaos of the American psyche as country music, and its current pivot back toward authenticity makes it ripe for an artist like Bingham. The 44-year-old exudes realness, which the former rodeo cowboy, New Mexico native, and Texas resident could exploit if he so chose. But the problem, as he sees it, is that any run at country music superstardom would likely mean alienating his longtime fans, the people who, after nearly a quarter century of following his career, have come to take possession of the songs that Bingham has written.

That transfer of power, so to speak, from artist to audience is what rekindled Bingham’s love of songwriting. With the support of a new backing band — the sublime Texas Gentlemen — Bingham is writing again. He’s also making peace with “The Weary Kind,” the song for the 2010 film Crazy Heart, which won him an Oscar and a Grammy, and, for a time, he refused to play live.

Today, the song is back in his set list, and will soon join tracks off They Call Us the Lucky Ones, his new album, out May 15. It’s Bingham’s first studio LP since 2019, his first with the Texas Gentlemen, and his seventh since his seminal debut, 2007’s Mescalito.

A concise 10 songs, nine of them written by Bingham, They Call Us the Lucky Ones contains a love song for his wife, Hassie Harrison, as well as a tale of narcotics trafficking in Mexico (“Cocaine Charlie”). At times, Bingham gets introspective; at others, he sings about eating marijuana gummy bears “in our underwear” (“Americana”). It’s as complete of a record as Bingham has ever recorded.

But for as naturally as it fits into his catalog, They Call Us the Lucky Ones almost never happened. 

Bingham hadn’t been writing much, save for 2023’s Watch Out for the Wolf, a concept EP he created while wandering the Montana wilderness. Then, the following year, he was invited to join the Last Waltz Tour, which features a rotating cast of musicians playing the music of the Band. Spending time in close proximity to supremely talented artists like members of Tom Petty’s Heartbreakers sparked something in Bingham.

“I’d met Don Was on the Last Waltz Tour, and we became good friends,” he says. “It was me and him and Mike Campbell and Benmont Tench all on a bus for a while. Talking to them and playing music every night, I just got inspired to write.”

In the process, he also realized he had accidentally become a member of a band: He and the Texas Gentlemen were now one.

The last time Bingham had a proper backing group was early on in his career, around Mescalito, with the Dead Horses. They parted ways in 2012, but Bingham had enough connections to find musicians when he needed to tour or record. When he landed the role of Walker on Taylor Sheridan’s juggernaut Yellowstone in 2018, he all but put music on hold.

However, in late 2021, Bingham decided to book a show at Billy Bob’s Texas in Fort Worth and sold it out. Quickly, he realized he couldn’t do it alone. His friends Nathaniel Rateliff and Charlie Sexton suggested the Texas Gentlemen. By that time, the all-star collective of Lone Star State musicians was well-established as a bar band and session group, and they jumped at the chance to play with Bingham.

“I hadn’t played in months,” Bingham says. “I hadn’t done any shows and had never played with these guys. No rehearsal. No nothing. We just showed up and winged it through this sold-out show at Billy Bob’s, and it was so much fun. It was so easy. They had my back.”

Bingham rang up the Gents again, for one-off gigs at Stagecoach, the Two Step Inn festival, and some National Finals Rodeo appearances in Las Vegas. He and the band couldn’t deny their chemistry, nor the friendship they were forging.

“It was vibey, right from day one,” Paul Grass, drummer for the Texas Gentlemen, tells Rolling Stone. “Ryan’s so laid back, and he’s such a great songwriter. It was just an easy relationship.”

THE TEXAS GENTLEMEN ARE BASED IN North Texas, most of them in or near Dallas, and have been playing together since 2014 — with a few lineup changes over time. The ones backing Bingham are Grass, keyboardist Daniel Creamer, guitarist Ryan Ake, and bassist Scott Lee. They also added Richard Bowden, who built a reputation as one of the best fiddle and mandolin players in Texas. Cody Huggins, a musician and longtime friend to Bingham, rounds out the group that played on They Call Us the Lucky Ones. The title track, the only song not written by Bingham, is a Huggins composition.

But it’s a song that Bingham came up with on the fly that underscores the bond between frontman and band. Near the end of his run on the Last Waltz trek in 2024, Bingham started making up a stream-of-consciousness song about his tourmates.

“I was literally just naming guys in the band,” he recalls. He called it “The Ballad of the Last Waltz Band” and played it once at a sound check before forgetting about it. Then, while recording what would become They Call Us the Lucky Ones at 7013 Sound studio in Fort Worth with the Texas Gentlemen, Bingham started playing his ballad, replacing the Last Waltz artists with the names of the Gents: “A guitar man on one side, a piano’s man’s left hand/Scott and Paul gonna hold it down, we’re the Texas Gentlemen.”

It was a band’s musical origin story and, on Tuesday, Bingham released “The Ballad of the Texas Gentlemen” as the latest song off They Call Us the Lucky Ones.

“It just made me think about being on the road with the band, which always makes me smile,” Grass says.

When Bingham finally had free time in his schedule, he and the Gents set out on a real, extended run. They called it the All Night Long Tour, modeled after Bingham’s time with the Last Waltz, and crafted an “evening with” concert: no openers, a 45-minute set, a half-hour break, and a 90-minute marathon. They decked out venues with cowboy imagery and stocked bars with Bingham’s Bourbon — one of his side ventures. During intermission, video screens played a series of outtakes featuring Bingham and the Texas Gentlemen.

By the time they rolled into Cain’s the day after Halloween 2025, the show was fine-tuned, and Bingham in particular was having a blast. He had Harrison in tow, along with two of their dogs, and the gig was a highlight of Cain’s year-long centennial celebration.

Before taking the stage, Bingham passed the time backstage at a pool table. A few feet away, Harrison put on a Marty Supreme-level clinic in table tennis, casually dispatching challenges from the Texas Gentlemen. When tour manager Joel Matzinger informs the gang that they’re due on stage in three minutes, Bingham fires back, “Nah, we’re on Tulsa Time tonight.”

Late in the first set, Bingham calls back to that “Tulsa Time” remark and launches into an impromptu cover of the song that Danny Flowers wrote and Don Williams made famous. “It might be a train wreck, but we’re gonna have fun,” Bingham tells the Tulsa crowd. He gestures for Harrison to join and she takes a verse, before wishing Cain’s a happy birthday.

Harrison spends most of the night in spirits as high as those of the band. Watching from the wings, she gives Bingham a good-luck kiss and an ass-grab before the house lights dim. During intermission, she spies a stagehand dressed in a white, Christ-like robe — likely left over from Halloween the night before — and insists on taking a picture. After the show, she floats around as Bingham holds court backstage. “He’s the most green flags I’ve ever seen,” she says of her husband.

The actress met Bingham on the set of Yellowstone in 2020 when Harrison took on the role of Laramie. For a while, they were little more than costars. Bingham’s first marriage to producer Anna Axster ended in 2021, and they shared parenting of their three children. Bingham, at least initially, was ok with being a single dad.

Two years later, though, he found himself at a charity event in Texas during a break in Yellowstone filming and met Harrison’s mother. They hit it off and she encouraged him to ask out her daughter, whom he married in 2024. Harrison’s impact on Bingham’s music has been, in his words, “a lot.”

“Writing songs, I would always think I needed to have a concept or a through line, and I’d put so much pressure on myself,” he says. “With Hassie and the kids, they’re all so present and in the moment. They’re not worried about the ifs and the afters. Between them and her, they put me in this headspace where I can just … write a song.”

Bingham insists the songs on They Call Us the Lucky Ones came about by happenstance, but he’s bluffing. Harrison challenged Bingham, whose catalog is rich in heartbreaking ballads like “The Weary Kind” and “Hallelujah,” to write a love song for her. He obliged and offered “Blue Skies.”

“She goes, ‘You got a lot of sad-cowboy songs. You need to write a few more glad-cowboy songs,’” Bingham recalls. “And I went, ‘You mean like this?’ and played, ‘I wouldn’t trade a blue sky, honey/For the way I feel for you.’”

“Blue Skies” is Bingham in his element, turning the rawest of feelings into simple lyrics impossible to misconstrue. It’s also the point on the record in which the Texas Gentlemen step back and yield the song to Bingham. It’s musicianship, sure, but it’s also an acknowledgment that Bingham changed their lives. They’ve got a good thing going, and they aim to keep it that way.

“It’s a great gig that we love,” Creamer says. “We’re playing these world-class songs to these big-time crowds that are loving what we’re doing. In some backing gigs, you hear, ‘Why are you playing that? You’re not sounding the way I want you to.’ Ryan is so happy with the sound that we make. Yeah, he’ll give broad-stroke comments, but it’s very open and extremely fulfilling. This is a time in our lives where we’re really locking in. Now that we’ve made an album together, it’s even more so.”

Bingham has that effect on a lot of people in his orbit. For his Cain’s shows, he invited rising songwriter Calder Allen to join him. Calder’s grandfather is Texas songwriting legend Terry Allen, a friend and mentor to Bingham, and he’s seen his own career take off over the past two years, landing opening slots for Shane Smith and the Saints and Jack Ingram.

At Cain’s, Allen sits in on guitar and swaps verses with Bingham on “Wolves.” It’s a cool moment, but it pales in comparison to the invitation he gets when the show ends. Bingham asks him to cancel his plans and jump in the bus for the week instead. On the spot, Allen accepts.

“That was one of the best weeks of my life,” Allen says of the tour. “I have looked up to Ryan as a songwriter for as long as I can remember. Every time I’m with him, I feel inspired to keep going. As a younger artist, having him as a mentor and reference has meant everything to me.”

Such an appraisal is the rule, where Bingham’s influence is concerned. There’s a perception, mostly in music business circles, that his time on Yellowstone transformed him into a Hollywood bigshot. It’s a perception in conflict with a man motivated more by seeing Calder Allen or the Texas Gentlemen taste success over himself, or the man who dropped everything last summer when Robert Earl Keen asked him to be a part of his flood benefit.

Bingham admits that he’s better suited for music than the screen. Maybe, he says, if the director Paul Thomas Anderson has a great music story to tell, he’d take another role. But acting, and the specific sort of fame that comes with it, doesn’t move him the way music does.

“I don’t have that bug for acting. I don’t have a passion for it,” he says. “I gotta do the music stuff.”

A lot has happened since Bingham last did music the way he is right now. It took finding his soulmates — personally in Harrison, musically in the Texas Gentlemen — to remind him of its place in his life.

Even when he wrote the song that brought him his biggest success to date, Bingham wasn’t as connected to country music as he is now. That happened in 2009, when he and T Bone Burnett co-wrote “The Weary Kind” for Crazy Heart, the Jeff Bridges film about a country singer, alcoholism, and journalism. It’s a song that arose from a pit of grief in Bingham’s heart.

“I wrote that about my dad,” Bingham says. “He committed suicide right about that same time. It was really heavy for me to play. I couldn’t hardly get through it.”

“The Weary Kind” went on to win the Academy Award for Best Original Song in 2010. The following summer, Bingham performed at Willie Nelson’s Fourth of July Picnic, and Nelson’s lighting director, a man named Budrock Prewitt, was taken aback when Bingham didn’t give fans the live rendition of “The Weary Kind” they were expecting.

“I didn’t play it,” Bingham recalls. “I was with Budrock after the show, and he says, ‘Why didn’t you play that song?’ I said I couldn’t do it. He goes, ‘It means a lot to a lot of people out there. It means a lot to me. I love it when you play it.’”

Bingham began adding the song back into his set.

“It really helped me heal so much, because I realized it’s not about me,” he says. “It’s about all these wonderful folks that are coming out here wanting to hear music and wanting to feel something. Once it helped me process that, it changed everything. Even what we’re doing now, it’s not about me. It’s about all these folks that are sharing this emotion. It’s helping them heal.”

Those folks will get that chance again when They Call Us the Lucky Ones arrives this spring. Bingham and the Texas Gentlemen are reprising their “evening with” run in celebration of the record’s release and calling it the “Still Gettin’ Away With It” tour. It kicks off May 22 in Pittsburgh.

When the tour is over, Bingham will return home to Texas. He and Harrison moved back there from California in late 2025, the result of yet one more realization Bingham had about what inspires him.

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“I’m back,” he says. “We’re living in Texas. The whole band’s in Texas. We’re getting a warehouse in Fort Worth where we can build a fucking jam place. This feels like I’m home.”

Josh Crutchmer is a journalist and author whose book (Almost) Almost Famous will be released April 1 via Back Lounge Publishing.

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