The Road Goes on Till September: Robert Earl Keen Talks Surprise Retirement

Robert Earl Keen was in his tour bus, riding down the interstate from D.C. to Charlotte in the early morning hours of Dec. 7, 2021, when he realized it was time to come to terms with a major life change. Lying awake in his bunk, Keen couldn’t stop thinking about a scene in Training Day where Denzel Washington’s character repeatedly tells a criminal to “make a decision.”

“I thought, ‘That’s what I have to do. I have to make a decision,’” recalls Keen, who began racing through the next year’s calendar in his mind. 

Thirty-eight days later, Keen posted a video to his social-media channels titled “Time Flies.” In his prepared speech, the 66-year-old singer-songwriter announced he’d be permanently retiring from live performing.

After running through the details, Keen began to choke up: “Although it might not be apparent here, I promise,” he said, his voice breaking before he quoted his most famous song, “the road goes on forever, and the party never ends.”

For Robert Earl Keen, the road now goes on until September, when the Texas cult legend will conclude four decades of touring with a final run of shows at Floore’s Country Store in Helotes, Texas. His last show will be Sept. 4 — fittingly, the day before Labor Day.

Before then, the wry troubadour will play a feverish final summer tour that’s already proving to be the most in-demand Robert Earl Keen ticket in decades. “I’m experiencing something I haven’t experienced in years,” he says, “which is what to do with all the friends and family I didn’t know I had.”

As Keen winds down his touring operation, he still plans to ramp up activity in just about every other facet of his creative life. 

He’s recording a studio album of originals due for release in 2023. He’s excited about his forthcoming multimedia project called Western Chill, which he describes as “a record, a video, a graphic novel, a songbook, and sort of a play.” He’ll be building sets and working on video production for future livestreams. He wants to start a consulting business of sorts where he can advise younger musicians on the pitfalls of the music industry. And he’ll be doubling down on the singer-songwriter interview podcast he works on with his daughter Clara Rose, who’s exposed Keen to an entire new world of music.

“I realized I was living in this fucking echo chamber on the bus, listening to Jackson Browne and Ray Price and Tammy Wynette all the time,” says Keen, calling from his home in Kerrville, Texas. 

During the conversation, Keen seemed at peace with his decision and happy to be at home, where birds were audibly chirping in the background. “There are a lot of things I want to do in music, but I’m not going to keep going on the road until I just wear out,” Keen tells IndieLand. “I have friends, like the folk singer Bill Morrissey, who died in horrible hotel rooms in nowhere, Georgia. I’m not doing that.”

Was this decision to stop performing something you’d been contemplating for a long time?
I had considered this for a couple years prior, but I had always stacked up all the obstacles to get through: How is this going to work out for my family? Am I going to have enough money? How am I going to deal with the band and make sure they’re OK? There would always be one or two things where I’d go, “I can’t do it now because this or that is happening.” Maybe there was a show on the calendar, or I’m stuck with a bus lease. 

Why now, then?
2021 was the roughest year I ever had across the board: career-wise, music-wise, touring-wise. The whole thing was really, really, really hard. Touring has really fallen apart. There was a big hole in the promotion business, so everyone said, “We can have this show in our backyard.” We ended up playing a bunch of barbecue joints, where they’d put a crappy wooden fence around it and sell food, in Texas and out in Montana. But you know how it is: live music is the last thought when these places are being built: “We’ll build an eight by eight plywood stage six inches off the ground, and get some Fisher Price speakers.” That’s what was happening. The sound was horrible. We would show up at noon and wouldn’t get to soundcheck until 7. It just flat wore us out. There were some [gigs] where I’d look at the numbers prior to the show and say, “These aren’t any good, we’re just going to bolt.” And then I had a couple guys who actually said they were going to pursue legal action. I had never dealt with that, ever, someone pursuing legal action if I don’t come and play to the ten people you sold tickets to. 

It just became a whole other world, a new world, and it wasn’t a fun world. There were places that were like, “Oh yeah, we do have a bathroom: It’s 300 yards from the stage and you have to walk through the restaurant to use it.” I’m sorry, we don’t do that. It was tough.

Do you think you’d be making the same decision to stop performing if it hadn’t been for Covid and everything it brought upon the live music industry?
That’s a good question. I’m not positive I would have. It had such an effect on my mental state. I’m very protective about my band and all the people who work for me, and I was ashamed to be dragging these guys into some of these shitholes we were playing. It made me feel bad, and then I got into a lousy mood, and I got cross with the guys I was trying to protect. If we would have just gone on and been moving in the same direction that we were [before the pandemic], I may have well stuck with it.

Not many artists get to retire from touring on their own terms. How have your peers reacted to your decision?
They’ve been very supportive. I got a lot of people thanking me for creating a map or some kind of exit strategy, because it’s tough. More than half of them aren’t staying on because they need the money. Let me say this: I’m not a spotlight hog, and I don’t need that much attention, so I don’t know what that exactly feels like. People say, “How’s it going to feel?” I can guarantee you, it’s not going to feel like I lost a whole lot. I’ll miss the bus as much as I’ll miss the spotlight. 

What can you share about the record you’re making in May?
They’re original songs. I have been working under this cloud of expectation of, “I’m supposed to put out my masterpiece or some kind of revelation about what it feels like to come out on the other side,” but I’m not really hitting it there. I’m actually just working on some really fun narrative songs, wordplay kind of stuff. That’s what I’ve been hitting lately.

Are you reserving the right to change your mind about this decision, like so many artists who say they are retiring from touring eventually do?
When I was a kid, I was a huge rodeo fan. My all-time sports hero is a guy named Phil Lyne, he won the all-around national championship two years in a row, and after he won his second all-around cowboy championship, he quit. He went back to the ranch and he’s still down there in George West, Texas, probably up at six in the morning drinking coffee and bitching about taxes. 

When I was a kid I thought, “That’s dignity. That’s how to walk away.” I got a hold of Phil’s family and I told him I would like to have Phil come up [to a show] and just stand there and let me tell that whole story and he can just wave his hand and walk away. And they said OK! So I’m looking forward to that: On the 3rd or 4rd of September I’m going to have Phil Lyne, my all-time sports hero, standing up on the stage, and I’m going to tell them about how Phil Lyne walked away from it all. 

Let’s say there’s a tribute show to an old friend of yours somewhere in Texas and you were asked to play a song. Are you ruling something like that out?
No, no, I don’t think that’s off the table. If we wanted to put a boundary around it, I’m just not going to play for pay. That’s it.

Have you thought about the last song you want to play on September 4th?
[Laughs]. No, actually, I haven’t. My mind just exploded. Really, I have to think about that? Maybe I should. 

How did you initially feel right after you filmed and posted your announcement that you were retiring?
For the next three days, I was in a weird fog like, “What have I done? How is this going to play out?” And then we went on a little seven, eight-day tour, and man, that was just the biggest release I ever had in my life. It was unbelievable. We usually play 100 minutes, and all of a sudden, we were bumping up against three hours. I was just up there talking about these songs and talking about shit I had never talked about, vomiting out this information feeling like I was in a confessional booth. It was the best time. I was completely unchained. 

What’s the worst gig you ever played?
I played one house concert that was a full-blown cross between Green Acres and David Lynch. It was awful. It was in Sacramento, which was not the greatest city. That was a terrible one. One show that would be more common, I would say, was one I played up in Indiana — I never had a strong following in the Midwest — and I was trying to get the audience’s attention, and I finally stopped. I don’t misbehave often onstage but I just yelled into the microphone and said, “Look, I’m going to play you one song that I think is a really good song, and if you don’t like it, you can keep talking. If you do like it, please let me finish my set.” I played “The Road Goes on Forever,” and they just kept talking, so I walked off.