Golden Age 2.0

The Million Dollar Cowboy Bar and the Silver Dollar Bar & Grill are intimate venues that bring in big country names thanks to the late owner’s vision and love of music.

// By Richard Anderson

// photography by bradly J. boner

It’s a cold and windy night in October of 2021, with snow on the ground and more on the way. But inside the Wort Hotel’s Greenback Lounge, it’s warm and cozy—and about to get warmer.

The Del McCoury Band has taken the stage in the historic downtown venue. The 100-plus capacity audience is finishing dinner—included in the $150 ticket price—and the 82-year-old bluegrass patriarch is tuning up his guitar and chatting and laughing with his younger bandmates. He’s also glad-handing with nearby guests and his hosts: Jim Waldrop, general manager of both The Wort and the Million Dollar Cowboy Bar; Steve Robinson, the Nashville-based music broker instrumental in making the evening possible; and another guy who is grinning ear to ear like a kid who just had his fondest wish come true—the owner of both The Wort and the Million Dollar Cowboy Bar just around the corner, Bill Baxter.

Tonight is a special night: a Silver Dollar Showcase Session—a casual, intimate, occasionally rowdy evening of live music from a top star, one of the many brainstorms Baxter had to restore The Wort and the Silver Dollar to their original glory.

Bill had a vision of a new Golden Age of music in downtown Jackson.”

—Justin Smith, entertainment manager at The Wort and the Cowboy 

In 2008, Baxter—a noted Tennessee businessman, philanthropist, and “ubiquitous board member,” according to KnoxNews.com—became the sole owner of The Wort, the downtown hotel that was conceived by Charles J. Wort, a homesteader who arrived in the valley in 1893, and was then built and opened by his sons in 1941. Baxter immediately set about making extensive but sensitive upgrades, starting with the renovation of every guest room. However, “He quickly learned that the bar was not sufficient to entertain at the level we wanted to make it more of a locals’ venue,” Waldrop says. “The critical part from day one was to get locals back into the Silver Dollar, and we felt we could do that with good music.” Baxter died in August 2024 at the age of 71.

The Wort Hotel and Silver Dollar Bar & Grill have hosted an impressive array of musicians over the years: Roy Clark and The Sons of the Golden West, Waylon Jennings, Glen Campbell, Jerry Jeff Walker, Arlo Guthrie, Doc Watson, and Leo Kottke. Rusty Draper, a singer and TV and radio announcer, booked two full weeks there so he could bring his wife and children on a family vacation. In the 1960s, bandleader Garn Littledyke invited a young fellow named Willie Nelson to play a few of his originals. However, while the hotel was rebuilt after a devastating fire in 1985, the Silver Dollar was diminished; guest rooms, a banquet room, and a small merchandise shop took over about half of its original space. 

After Baxter finished the remodel of The Wort’s 55 guest rooms, he turned his attention to the Silver Dollar. The Silver Dollar’s original footprint was reclaimed, the stage restored, the sound system improved, and a second bar that mirrored the details of the historic bar, down to its inlaid 1921 Morgan silver dollars, was built. 

“It would have been a lot easier and a lot less expensive to put in a regular bar as opposed to an exact replica,” Waldrop says. “But [Bill] was adamant about that.” The space was also made to be flexible; it can be one large room that stretches from the bar and grill’s main entrance on Broadway Avenue, or removable, soundproof panels can be installed to create the cozy 350-square-foot Greenback Lounge.

“Bill had a vision of a new Golden Age of music in downtown Jackson,” says Justin Smith, entertainment manager at The Wort and the Cowboy, which Baxter acquired in 2017 and also upgraded. “We came in and spent a lot of money keeping it the same,” Waldrop says. “We loved so many things about that, but we put different lighting in to highlight different aspects of what’s behind the bar and some of the architectural pieces that we felt were so much a part of the Cowboy.” The burled pine, the taxidermy critters in glass cases, the Western kitsch, and the culture all stayed the same, but removable segments were designed for the stage to accommodate larger ensembles, and tens of thousands of dollars went into the sound system. “We wanted to have top-of-the-line equipment for when we were recruiting some of the bigger names,” Waldrop says.

And the big names came, with the help of Steve Robinson, who at one point in his career was tour manager for Randy Travis and remains well connected in Nashville’s music scene. Robinson had gotten to know Baxter in the late 1990s when Baxter, as commissioner of economic and community development for the State of Tennessee, went looking for quality musical artists to entertain bigwigs he was courting to move to his state.

“When they had a visiting delegation—VW, Nissan, or whoever—in addition to the real nuts-and-bolts business they were attending to, we would do little private shows for a group of 50 or 200 in a ballroom or venue,” Robinson says. “They would hire us to produce these shows,” folks like Kenny Chesney or Jo Dee Messina. “That’s where Bill and I first started working together.”

With Robinson’s help, the Cowboy has brought in the likes of Clint Black, Riley Green, Luke Grimes, and Ned LeDoux. Hank Williams Jr. played there in 2020, the first big act after the COVID-19 pandemic, and Kevin Costner brought his band for the only gigs he had played in four years, Waldrop says. “He was weighing that against four shows in California and opted to come to Jackson. He stayed a full week, played two shows that sold out in like eight minutes. We sold tickets to buyers in 41 states—that really exemplifies Bill’s vision.”

The Silver Dollar’s Showroom Sessions were the result of a “simple conversation,” Waldrop says. “Bill loved songwriters and was enamored with songwriting. So, one day he said, ‘I want to bring in songwriters,’ and somebody said, ‘Let’s call it “The Sessions,”’ and I said, ‘Let’s do dinner.’”

Robinson produced the first Showroom Session on October 18, 2018, with Steve Wariner, a Nashville country singer, songwriter, and guitarist whose string of hits dates back to the 1970s. Since then, the Greenback Lounge has hosted Doc Powell, Mac McAnally, Tommy Emmanuel, Jerry Douglas, Scott Emmerich, Dailey and Vincent, Rob Ickes and Trey Hensley, Blue Highway, and a young songwriter named Jenny Tolman, who greatly impressed Baxter.

Tolman met Baxter when she played a Showroom Session in October 2020. “I played the show, and after, he came up to me and wrote me a check on the spot because he felt that he didn’t pay me enough after he had seen the show,” she says. “I was blown away—I’m some unknown artist that he’s taking a chance on.” She came back the following year to open for the band Midland. “At the end of that, he comes up to me and he says, ‘You know, I really want an all-female festival … and I want you to be the face of it. Will you help me put it together?’” Tolman says.

“He became such a huge supporter of me. He honestly gave me the biggest blessing of my career, to host and curate Cowgirls at the Cowboy,” says Tolman, who, like Baxter, fell in love with the Tetons. She got engaged on the shore of Jenny Lake and then got married here; filmed the video for her song “Married in a Honky-Tonk” in the Cowboy; and has returned each October to organize, host, and perform at Cowgirls at the Cowboy, a three-day showcase at the Cowboy Bar that is still the only all-female country music festival in the country.

Another bright idea Baxter had was the Million Dollar Music Fest, a free day of country-rock by stars and up-and-comers held over Memorial Day weekend on Town Square since 2019, which in 2025 drew about 6,000 people. “He said, ‘I want a festival, a big fest,’” Waldrop says, “‘And I want to do it outside.’” They accepted some funding from the Jackson Hole Travel & Tourism Board, but only for one year. Baxter wanted the community to know that this was a gift, Waldrop says.

“He put so much of his time and love into the Cowboy and Silver Dollar, into making sure people had a good time,” Tolman says. “You can tell by how the music scene has blown up … the type of artists we’re able to bring in is unprecedented.”

It’s not accidental but the result of a well-thought-out strategy: bring artists in, let them enjoy a few nights or a week at The Wort, with their family if they wish, like Rusty Draper did back in the day. “They go see the Tetons, go on a wildlife tour, whitewater raft, and play a show, too,” Waldrop says.

Like so many who experience Jackson Hole, they fall in love with Jackson Hole.

“It works,” Smith says. “They go back to Nashville and talk it up: ‘You got to go!’ That was the vision—give them such a good experience that more want to come and do it.”

“Why would Hank Williams Jr. come here to play?” Smith asks. “It was the promise of a unique time in this mountain hamlet. And then that picks up momentum. Other famous musicians see pictures of Steve Wariner and Larry Gatlin on the wall and say, ‘OK, I see what you’re doing.’” They build trust within the relatively small circle of Nashville-centered artists, Smith says, and among regulars, who come to trust that whatever The Wort or the Cowboy offers, it’s going to be good.

COMING THIS WINTER

January 22: Grammy-nominated country-rock singer/songwriter  ERNEST makes his debut at the Million Dollar Cowboy Bar. Tix at milliondollarcowboy.bar.com

Find additional concerts at:  @milliondollarcowboybar @worthotel worthotel.com JH