New Wave of Road Retirees Hope to Fare Well in Their Golden Years

Tom Roland
·6 min read
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In recent weeks, The Nitty Gritty Dirt Band, Doug Stone, John Michael Montgomery, Ray Stevens and Lee Greenwood have all publicly announced plans to wrap the road portion of their careers. They’re hardly alone.

The Oak Ridge Boys started their farewell tour this past fall, though tenor Joe Bonsall, suffering from a neuromuscular disorder, was forced to hang it up at the end of December. Dolly Parton recently revealed that she had decided not to return to the road since she wrapped her last tour in 2016. Additionally, country/rock band The Ozark Mountain Daredevils and the Eagles, whose current lineup includes country artist Vince Gill, are also concluding their regular concert routines. (Gill will continue to work as a solo act.)

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Retirement is a well-earned rite of passage for most people in later life, though there are plenty of musicians — Willie Nelson and the late Tony Bennett and B.B. King are good examples — who maintain a road life until their bodies give out. They find it difficult to stop, spurred by fan adoration, good paychecks and/or the simple joy of performing.

But this new wave of retirees is generally finding it easier to hang it up after experiencing an extended home life during the pandemic. Once their tours were canceled in 2020, most country artists found themselves anchored for 12 to 24 months. Artists in their prime couldn’t wait to get back out, but those on the back end of their careers began to recognize that if they ended their road-warrior phase, it wasn’t necessarily the end of the road.

“We got a dose of our real life,” Nitty Gritty Dirt Band co-founder Jeff Hanna says.

The benefits include the kinds of everyday events that can’t be experienced from 1,000 miles away: dinner with a spouse, attending a daughter’s graduation or playing with the grandkids in the backyard. Making music for a living is attractive — none of the retirees wish they’d dug ditches or balanced books instead — but it involves sacrifices, and they discovered the opportunity exists to stop and smell the roses at home.

“We’ve got enough to retire on, so why not enjoy the rest of my life with my family?” asks Stone, whose 13-year marriage has produced a 7-year-old daughter. “We love going to Disney. I want to go see the redwoods and stuff like that.”

That yearning to explore the world is part of the attraction for young musicians, and in the early years, America’s topographic diversity can help keep a touring job interesting. But heavy concert  schedules don’t usually allow much time to play tourist. Stone remembers one trip in upstate New York when the bus came within a 10-minute drive of scenic Niagara Falls. They had to bypass it stay on time, and he has never been back.

“I didn’t get to see America,” he says. “I got to see the back seat of a bus.”

The current wave of road retirements is actually a sign that some of Nashville’s structural changes have worked. Many of country’s previous legends — Hank Williams, Jimmie Rodgers or 1960s/1970s-era George Jones — faced financial problems after spending lavishly during their peak commercial years. Since then, business management companies have sprouted, helping modern acts plan their financial futures. Where many of their predecessors were required to tour until they couldn’t stop, modern acts have options.

“Most of them over the decades have gotten smarter in terms of managing their finances,” says Action Entertain Collective booking agent Travis James, who represents Montgomery and several other ’90s-associated acts. “Are there exceptions to that? Sure. There’s always going to be people that piss their money away with divorce or drugs or whatever the case may be. That’s in accounting and that’s in the NFL — it’s in everything. But by and large, the artists that were viable enough to have long careers and a show full of hits, even if they didn’t do it right the first half of their career, they figured out how to do it right the second half.”

Not that everyone is thrilled about hanging it up. During the COVID-19 break in the concert schedule, The Oaks missed the stage, missed seeing their fans and longed to make music again.

“That’s all we do in our lives,” bass singer Richard Sterban says. “We go out and entertain people and help people with our music. And we were not able to do that, so we didn’t necessarily like that feeling.”

Still, long rides on a sedentary tour bus and the repetitive motion involved in making music take a toll. Greenwood has titanium knees after several surgeries and had back surgery in 2020. Hanna blew an Achilles tendon in 2019 and now walks for exercise instead of running. And he has experienced some issues with his left hand — “which is kind of the money hand on the guitar,” Hanna says. “I have to play a little differently now.”

The body sort of makes retirement inevitable for most — “Like [Jimmie] Fadden says, ‘Do the math,’ ” Hanna quips — but modern artists’ money management makes it easier to take that step.

Greenwood, Stevens and Stone all plan to conclude their regular concert schedules in 2024, while Montgomery expects to wrap in 2025. The Oaks and Nitty Gritty Dirt Band could go on for years, in some cases picking the venues based on sentiment rather than income.

“We would prefer to go back to familiar places, to go back to people that we know,” Sterban says. “Basically, we want to perform in front of people that have helped make us who we are today.”

But the demand goes up once promoters and fans realize the artist’s shows are coming to an end, which also increases the price for many bookings. That’s the good news for the agents, though farewell tours are bittersweet for them, as they lose valuable clients.

“When they tell me they can cut back, that doesn’t help my financial bottom line,” James says. “I can’t sit here and tell you that I’m necessarily happy about it, but I sure am proud that I was part of the solution in helping them fulfill their goals professionally.”

If they retire early enough, the artists may be preserving themselves, too. Extended travel is physically challenging at any age. They’ll very likely miss the stage, but maybe not the wear and tear required to get there.

“I want to be on the planet,” Stone says, “not in it.”

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