The End Of The Road: Robert Earl Keen Maps Out His Next Chapter

Shortly after announcing Jan. 14 that he would retire from touring in September, Robert Earl Keen read an essay in The New Yorker by David Sedaris titled “Lucky-Go-Happy” that described the author’s return to the speakers’ circuit after sitting idle for months thanks to the lingering COVID pandemic.

“Boy, I’ll tell you what, he nails it on touring … as good as anything I’ve read or heard by anybody,” Keen says of the piece. “I mean, he’s so funny, but it was like from A to Z, you know? From the very beginning to all the way through.”

Keen thought back to when he was just a kid and the concept of retirement – though not necessarily his own – entered his young head.

“I’ve always thought, since I was a little kid and I saw Roy Rogers at the rodeo, what’s the deal? Why do people keep going on like that, you know?,” Keen rhetorically (and maybe a little blasphemously) asks.

After more than four decades of touring, Keen – a beloved, deeply Texan artist whose best-known hit is titled “The Road Goes On Forever” – still doesn’t have a good answer for that. He also doesn’t intend to find out.

Instead, he’s jumping off the road – or at least taking a detour on a less traveled fork of it – at the peak of his artistic powers. It’s a well thought-out plan and potential roadmap for others yearning to exit but seeking an off-ramp.

“People get to a point … where they’re going to be bored to death singing the same couple of hits over and over. And I thought that’s not the way I wanted to do it,” Keen, only 66, says. “The last couple of years, and not related to COVID at all, did give us all some time to pause and reflect. During that time, and even before that, I had been toying with the idea of how to exit from this business. It was always, ‘I gotta get through this’ or ‘I gotta put out this record’ or ‘I have to do whatever deal I have with this record company or publishing company or whomever.’”

In late 2020 and into 2021, at first in Texas and then throughout the Plains States and Southwest, Keen found himself playing some of the worst gigs in his long memory. He’d mortgaged his house to keep his band and team on salary and with benefits. He did livestreams and shot videos for sale from his home studio to help supplement that income.

Keen is one of a class of Texas born and bred singer-songwriters including former college roommate Lyle Lovett, James McMurtrey, Steve Earle, Charlie Robison, and the late Guy Clark, Jerry Jeff Walker and Townes Van Zandt who are rightly hailed for their literary songcraft but not part of the Nashville country music machine.

“In the state of Texas, they had this loophole where if you served food, nobody had to mask up or any of that stuff,” Keen explains of the unique, if peculiar, Texas touring landscape in 2021. “They have these barbecue restaurants, and I mean shacks way out in the country, where they have like two acres of fenced-in area. And the last thing the promoters think about is music.

“They’d have pallets pushed together [for a makeshift stage] and a price that’s terrible. I’m not saying that they weren’t lucrative, but there were a lot of people that would show up that weren’t there to see [the show]. They just like to go out on a Friday or Saturday night, drink beer, eat some barbecue and pretend the pandemic didn’t exist. Everyone was an amateur promoter and everything was underpowered and there was a problem every day.”

Keen, REK to fans, peppers stories with cultural references. He says he kept going back to the film “Training Day” – there’s a NSFW prison yard scene in which “make a decision” became a catch phrase – “and I thought, what I need to do is ‘make a decision.’ I just need to pick a date and go with it.’”

He is nearing the end of his final circuit of favorite venues before retiring from the touring life after one last, month-long “World Tour Of Texas” leg, ending with a three-night stand on “home turf:” Floore’s Country Store in Helotes, Texas, Sept. 4.

“The news of his retirement was truly out of the blue,” Wasserman Music agent Seth Malasky tells Pollstar. “Robert set a call with us mid-January and just dropped the news. He’d told his family and his internal team and band, then let us know. We were all frankly shocked. We quickly realized we had this one moment to rethink the next nine months and put together a final run of dates that truly honors his legacy.”

His upcoming release, Western Chill, may offer a glimpse of what’s to come. It isn’t a traditional album so much as it is a multimedia project, complete with an 80-page graphic novel, a short film and, of course, new music. It is expected to be released Aug. 26, digitally and on vinyl (though shortages may delay delivery).

The final tour is titled “I’m Comin’ Home,” and it’s apt. Home is his ranch between Kerrville and Medina, Texas, just northwest of San Antonio. It’s also where his home studio, which he calls the Snake Barn Movie Ranch, is located.

As the name implies, it’s not just a music studio and, by all accounts, Keen will be spending a lot of time there charting his next path and creating new art in a space that touring never allowed much time for until now.

After all, Keen has been a road dog his entire career. Manager Cindy Howell and her husband leased tour buses to Keen in the 1990s but, after about 10 years, Keen’s then-bookkeeper called to tell Howell that she was leaving, and Howell applied for the job. She learned the business of REK and is now his day-to-day manager with Keen Productions.

Pollstar first put Robert Earl Keen on its cover as an emerging “Hotstar” in February 1998, but he was already well-established as a prodigious touring artist by then. The first box office report submitted to Pollstar was for a June 1989 gig at Canal Street Tavern in Dayton, Ohio: 36 tickets sold for a gross of $216.

In the early days, Keen was booking himself – and admittedly not very good at it. “I was more kind of the Brute Force of Ignorance Booking Agency,” Keen told Pollstar at the time.

Having released his self-funded debut album, No Kinda Dancer in 1984, he began playing just a few small venues around San Antonio. Realizing that probably wasn’t going to provide much of a career trajectory, he cast his net wider – sometimes to the chagrin of the club bookers with whom he’d developed some history.

“I have had some serious knock-down, drag-out fights about the whole thing,” Keen said in 1998. “And as a matter of fact, in 1991, we had an argument with a bunch of little-bitty-deal promoters around San Antonio.”

But the strategy paid off, with Keen drawing 1,000 fans and more, finding audiences beyond San Antonio at places like Austin’s Cactus Café, New Braunfels’ famed Gruene Hall, and even Kuumbwa Jazz Center in Santa Cruz, Calif., where he sold 400 tickets – mostly to college students – as early as February 1991.

He put those cities and more, where he’s built strong fan bases over the years, on his “I’m Comin’ Home” itinerary.

“There were clearly markets and venues that were important he visit one last time,” Malasky says. “And Robert, after 41 years on the road, knows better than anyone else what those rooms are and where the fans want to see his shows.”

But he was, and is, especially loved in Texas – his “I’m Comin’ Home” tour ends with a monthlong barnstorm through his home state.

“The idea of ending his touring career by playing every major market in Texas was the first idea Robert had about how to close out this remarkable chapter,” says Noah Plotnicki, Wasserman Music senior coordinator. “He wanted to send a love letter to the state and to the fans throughout whose support has propelled his career. Robert selected the venues most important to him and we routed it. The cherry on top is the revival of his festival brand, Texas Uprising, at the Cynthia Woods Mitchell Pavilion in Robert’s hometown of Houston.”

Though Keen is indelibly identified with Texas, he did leave his home state, briefly, and relocated to Nashville but two years later moved back, having decided Music City was not as interested in live music as it was in recording and publishing. He’d signed with Keith Case & Associates there but eventually he moved to Monterey Peninsula Artists and, after bouncing around a bit, returned and found stability with agent Jonathan Levine, now EVP and executive partner at Wasserman Music.

In the meantime, albums like Gringo Honeymoon, Gravitational Forces and The Rose Hotel followed, as did a slew of live albums. His songs tell stories from the drunken yet joyous trailer park Christmas party of “Merry Christmas From The Family” to the down on his luck but not out of friends protagonist of “Feelin’ Good Again.”

Thanks to that mother lode of literate and loveable songs, and a staunch work ethic, Keen built and maintained a career well into the aughts as a touring performer and on festival stages.

Since January 1999, he has submitted 552 headlining and 41 supporting box office reports to Pollstar, totaling 640,029 tickets sold and a gross of more than $18.9 million. That doesn’t include soft-ticket events like Stagecoach, Hardly Strictly Bluegrass, Railbird, Willie Nelson’s Fourth of July Picnic, Austin City Limits, MerleFest, Tin Pan South and many, many more.

Keen credits Levine with guiding him through the horrors of 2021, and Keen will remain on the agent’s roster as he plays the occasional tribute show or benefit one-off.

The full-service agency will support his new endeavors, whether they be film, visual art, music or wherever his creative juices take him.

“We are here to support Robert in all of his creative pursuits,” confirms Wasserman Music’s Lynn Cingari, another member of the agency’s Keen team. “While we’ve mainly been focused on REK’s touring for the past years, we regularly aid clients in other artistic and business pursuits. We are excited to champion Robert as he enters this next phase of his career.”

Of his Wasserman team, he’s worked with Levine the longest and the agent numbers Keen among his friends, as well as a client.

“I love Robert dearly. I love the friendship that we’ve cultivated that extends beyond our working relationship,” Levine says of Keen. “A conversation centered around his decision to retire from touring is something we respect immensely.

“Robert wants to do it right, while he’s still relevant. The quality of everything he stands for, combined with this approach to his art and retirement before the flame diminishes, defines the word ‘dignity.’” Levine adds. “It’s bittersweet, but I think what he’s doing, and how he’s going about it, like the man himself, speaks to the grace and style that’s been the hallmark of his career.”

Howell will remain with Team REK as well.

“Right now, we’re just getting through the tour, and this is something that not many people have done. He has such an outline and a map of how other artists actually can do this, because sometimes the music business is like the Mafia – you can’t just leave!”

As for the end of the current phase for Keen, “It’s going to be joyful and sad at the same time,” Howell says.

“I have shed more than a few tears since Jan. 14, and I’m sure I will shed some more. But I’m so happy he is doing this for himself. He’s going out at the top of his game, which we all want to do. He’s not going to just sit on his rocking chair. He has so many things going on in his mind that he’s never actually had the time or opportunity to pursue.”

Keen seems pleased with the way his plan turned out.

“My plan was to announce my retirement and to go as far as I could with it. We’ve done a pretty good job of it.”

It took more than luck to get Keen to this place in his career, but one thing is certain: with his determination and the support of his loyal fans and inner circle, he’ll go to the next phase happy.