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Six days at sea with 1,200 Outlaw Country fans, two years into a pandemic

Stars, coronavirus tests and an endless buffet do their part as the cruise and music industries make a return

From left, Steve Earle, Roger Alan Wade, Elizabeth Cook and Mojo Nixon as the 2022 Outlaw Country Cruise kicks off in Miami. (Will Byington)
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SOMEWHERE IN THE CARIBBEAN — It’s just past 4 on a Friday in February when Carlee Thomas takes to the pool deck stage to lead the opening toast of the Outlaw Country Cruise. Steve Earle is playing the first set, branded the “Sail Away,” but the Norwegian Pearl won’t be leaving port for two more hours. Carlene Carter’s flight to Miami is late; the ship is standing by so the singer can hop on.

“Thank you for being here!” screams Thomas, who serves as “senior warrior” for Sixthman, which is owned by Norwegian Cruise Line and presents everything from wrestling to music festivals on the company’s fleet. “Thank you all for sticking with us.”

Servers circulate plastic shot glasses containing a pinkish substance.

“It looks like they’re bringing us our psych meds,” says David Mansfield, the multi-instrumentalist who played in Bob Dylan’s Rolling Thunder Revue.

After the toast, Earle takes the stage with the Dukes, his band, and kicks into a grinding version of his anthem, “Feel Alright.”

On paper, this might not seem like the golden ticket. Take 1,200 country fans weary from two-plus years of pandemic and put them on a six-day cruise with a buffet, a booze package and masking rules that just aren’t going to be enforced. And do this when the surge of omicron might be subsiding but has not disappeared.

Some are clearly leery. After five straight sellouts, Outlaw Country Cruise 6 is only about 60 percent full. Even those aboard have doubts.

Singer Laura Cantrell, who is married to SiriusXM satellite Outlaw Country programmer Jeremy Tepper, says that she was expecting a “s--- show, and that 20 percent of the bands at least would have band members that didn’t get on board.” Then she arrived at the Port of Miami that Friday. Whether you were Emmylou Harris or a first-time cruiser in a room without a porthole, you had to show a vaccine card and take a coronavirus test. And if you tested positive — as did Waco Brothers mandolinist Tracey Dear — you were shuttled off to a cheap hotel and not allowed to sail. In the holding room, waiting like everyone else for the results, Cantrell began to feel better about the Pearl.

“Maybe we’re emerging from whatever the latest wave was,” she says, a few days into the cruise. “Between vaccines and good practices, maybe we can move forward. I mean, I’m still not totally sure.”

The pandemic has been a slog for everyone, but it’s been particularly brutal on the two industries represented on the boat. In the early days, cruises teeming with infected passengers were kept at sea, which was miserable for the passengers and a public-relations nightmare. Then the industry shut down.

Norwegian Cruise Line started back last July, and in the fall Sixthman returned with events, including cruises with Kiss, Melissa Etheridge and Joe Bonamassa. Outlaw Country, originally set for February 2021 and co-organized by SiriusXM’s Tepper, had been postponed to this year. With omicron surging, Norwegian offered ticket-buyers a chance to bump their cabins to a future festival, including 2023’s “Outlaw Country Cruise” or “Outlaw Country West!,” which will sail from Los Angeles in November. Hundreds took up that offer. A few weeks ago, Tepper found himself texting friends and musicians with offers of free cabins. (A berth can cost anywhere from $1,580 to $5,300 — excluding a drink package.) That’s how Josh Kantor, a talented musician who is the organist for the Boston Red Sox but also plays with Wilco and other bands, ended up hauling his accordion onto the Pearl. During the cruise, he sat in with multiple acts, from Cantrell to the punkier Waco Brothers.

As hard as the pandemic’s been on the cruise industry, it’s been just as brutal on musicians. The ship’s headliners — Lucinda Williams, Earle and Harris — have been able to play gigs while maintaining a safe, social distance from crowds. Others have been more desperate.

Linda Gail Lewis, 74, the younger sister of Jerry Lee, says there were times she couldn’t make the $549-a-month payment on her Nissan Altima.

“It financially ruined me,” says Lewis, on her first Outlaw cruise. “I had four tours in Sweden that were canceled. I lost so much money and I had no money. I get little piddling gigs around Texas. You can’t make huge money playing locally because everybody wants to. And of course, Texas is wide open. And as scared as I was of that virus, I went out and did gigs before I could get the vaccine.”

Albert Lee, 78, the guitarist who has played with Harris, Eric Clapton and the Everly Brothers, ate through his savings. Lee’s inactivity also took a physical toll. He doesn’t practice offstage and keeps loose through a lifetime of steady gigs.

“Over the last two years, my hands just weren’t working like they did before,” he says, bending his fingers as if to show how they were stiffened.

And Sarah Borges, 43, who has recorded seven albums and had an eighth ready for release, spent the pandemic using the band’s Ford Econoline making courier trips from Boston’s Logan Airport. She was crushed when Tepper didn’t invite her to cruise for a third time. Then her fans began to post on the Outlaw Country Facebook page and make memes and tag Sixthman. Eventually, Tepper called. She would be a late add.

Borges brought enough clothes to change three times a day, from a purple sequin-and-ostrich-feather dress she got for $19.99 on eBay to a black Boston T-shirt in deference to her hometown. Then Sarah Shook, the North Carolina-based singer, came down with the coronavirus. Borges got bumped onto a special SiriusXM program onstage with singer and radio host Elizabeth Cook.

Tepper sat in the front row, nodding and laughing as Borges and Cook talked. “This isn’t a DJ talking to an artist,” he tells a reporter. “This is an artist talking to an artist. Just two girls talking.”

Later, Tepper was asked whether Borges had earned a spot on next year’s cruise.

“I don’t know,” he says.

But wasn’t she great?

“She’s awesome,” Tepper says. “But everybody’s awesome.”

You hear it over and over, from passengers and also musicians: I’m not a cruise person. I’ve never been on a cruise before. Normally, I’d never do this.

Which is to say they’re not here for the unlimited buffet or overpriced trinkets at the touristy port stops — Costa Maya, Mexico; and Harvest Caye, Belize — or to drink icy margaritas until they can’t tell Willie Nelson from Willie Mays. Most say they are music fans and blown away by the program.

“If you told me in 2015 that I’d be going on a cruise once a year, I’d have said, ‘You’ve got the wrong person here,’ ” says Marie Lekumberry, 61, who owns a restaurant in Gardnerville, Nev. “Now there’s nowhere else I’d rather be at this moment.”

That goes for the performers, as well.

“I don’t want this to sound the wrong way, but is this work?” says Lucinda Williams, sitting in her suite on the 14th floor of the Pearl. “We’re on this ship, which still blows my mind when I open up the curtains when I get up and see the ocean.”

Jon Langford, the Welsh-born punk veteran of the Mekons and Wacos, remembers coming on board in 2020 for the first time.

“We had our guard up and we were just like, ‘I need a room to get away and hide,’ ” says Langford. “But after a couple of days you realize all the people on this boat are all music lovers and they’re respectful, really polite. I was never in my room.”

For cruisers, the slate can be overwhelming. You wander out of a Williams show in the Stardust Theater and find Linda Gail Lewis banging out “Whole Lotta Shakin’ Goin’ On” in a crowded bar, or the Beat Farmers, on the pool deck, playing an amped-up cover of Neil Young and Crazy Horse’s “Powderfinger.” There are shows recorded for SiriusXM, home of the Outlaw Country channel, and there are the guitar pulls, during which Williams, Harris, Rodney Crowell and Earle sit onstage and trade stories and songs. On this cruise, there’s a tribute to Crowell, 71, which he caps by leading a star-studded cover of Dylan’s “When I Paint My Masterpiece” that includes Mansfield on mandolin. (Known for his musical exploits, Mansfield once played miniature golf with Gram Parsons.) Characters like cowpunk instigator Mojo Nixon and legendary road manager Phil Kaufman, who famously stole and then ritualistically burned the body of Parsons in Joshua Tree back in 1973, are given plenty of mic time.

And when the music finally wraps, nobody’s hopping in a van to drive through the night to a gig in Millersville.

“I’ve been playing music professionally since 1980 and I’ve never been treated better as an artist,” says Eric “Roscoe” Ambel, the producer and guitarist who has been in bands with Joan Jett and Earle. “There’s no real distinction between the absolute top tier. This artist pass gets you in anywhere you want to go. As a professional musician, even if you’re on a big festival, you never get to see this.”

That goes for the late-night artist parties. On the 14th floor, starting at midnight, they gather in a spacious suite that includes an open bar, a piano, and guitars and basses leaning against the wall. At the first gathering, Pete “Wetdawg” Gordon, a high-energy pianist who plays with Nixon, coaxes Lewis over to the keyboard, where she sings “You Win Again,” a 1958 hit for her brother. Keith Coleman, 65, a fully adorned Elvis impersonator from Tampa Bay, takes the microphone to churn out “Jailhouse Rock,” and grizzled Supersuckers guitarist “Metal” Marty Chandler picks up an acoustic. Eventually, Williams arrives to catch up and keep time with a shaker.

Tepper plays down his role, but by all accounts, he’s responsible for curating this cruise. At 58, he’s a kind of benevolent schmoozer, albeit with a fan’s ear and a music geek’s knowledge. He played in the World Famous Blue Jays, launched a record label, and served as editor of Vending Times and Wrestling’s Main Event magazine. In 2000, as DJ RigRocker, Tepper began spinning vinyl in clubs.

He won’t put down commercial country, but he doesn’t take to songs about short-shorts, pickup trucks and bros, favoring the harder-edge twang pioneered by Willie Nelson, Waylon Jennings, Billy Joe Shaver and later Williams and Earle. In 2004, after a set at Irving Plaza, Stevie Van Zandt, Bruce Springsteen band member and SiriusXM programmer, tapped on his shoulder and recruited him for Sirius. Today, he’s program director for Outlaw Country and Willie Nelson’s Willie’s Roadhouse channels on the satellite network.

On the boat, Tepper is a constant presence, his long hair tucked into a bun under a trucker cap, roaming the crowd and backstage areas.

“He’s a musical genius,” says Anthony Diaz, Sixthman’s chief executive. “These aren’t just concerts on a cruise ship. These are environments where you set the stage for collaborations and moments that do not happen on land.”

In 2020, that meant bringing reggae icon Lee “Scratch” Perry on for a cruise to Jamaica, featuring a tribute to Kris Kristofferson. For 2022, Tepper cooked up a reunion of Harris’s 1970s “Hot Band” with guitarist Lee and singer Crowell. In another theater, guitarist Bill Kirchen held a tribute for his pioneering country rock swing band, Commander Cody and His Lost Planet Airmen. The cruise’s musical highlight may be the return of Williams, who has been recovering from a 2020 stroke.

On the first night of the cruise, Williams’s road manager, Travis Stephens, walks her onto the Stardust Theater stage and positions a chair next to her so she can lean on it for support. But then Williams, the queen of richly detailed story songs that drove the rise of alt-country in the 1990s, begins to sing. The 2020 stroke has clearly hobbled her — she can’t play guitar and tires more easily — but her artistry remains intact.

“Her voice is completely there,” says Harris, who will share the stage with Williams twice during the week. “Her soul, her genius is still there, and nothing will ever take away the things that are still unimpaired.”

During a second performance, on the pool deck, Williams has to deal with a wind so strong it blows over her monitor. Stephens races onstage to tape a set of lyrics to a music stand. Still, Williams manages to deliver a scathing criticism of Russia before a pitch-perfect performance of “Man Without a Soul.” Afterward, in her suite, she will admit that she was touched by the way the cruise crowd responded after she talked about her recovery.

“I just told the audience what was going on and was honest with them,” says Williams. “It’s heartwarming. The audience applauded as I walked out, like kind of welcoming me back, and they had their arms open to me.”

The one thing this boat isn’t showcasing is politics.

That’s surprising, considering that country music is, as an art form, a microcosm of America. There’s the Steve Earle branch of the country party, which leans hard to the left, and the Travis Tritt axis, which strongly supported Donald Trump.

At the beginning, this latter group seemed more visible. In 2016, the first Outlaw Country Cruise launched as a partnership between Norwegian’s Sixthman and Renegade Circus, the live event division of Van Zandt’s company. It came after Lynyrd Skynyrd’s “Simple Man” cruise had wrapped in 2014. Some of the passengers seemed to be holdovers.

Steve Goldberg, who runs a cybersecurity company in Newton, Mass., remembers sitting at a cafe with his wife, Carol.

“And a guy had a giant Hillary T-shirt with bars and, like, ‘Lock her up’ and a MAGA hat,” says Goldberg. “And we’re like, ‘Oh, gosh, get me out of here.’ ”

By the next year, the shirts were gone. So were the flags.

“I ran all the f---ing Confederate flags off almost single-handedly, trust me, by refusing to sign their s--- and bad-mouthing Donald Trump,” Steve Earle says over lunch in the artists’ lounge. “And they all just went away and they got replaced by other people because there’s waiting lists for all these cruises.”

On the Pearl this time, some wondered whether the vaccination requirement cut out those on the far right. A few past cabin holders had posted angry comments on the Outlaw Country Cruisers Facebook page. Others told their friends they weren’t going if they had to get the shot. Lee’s regular drummer, Jason Smith, wouldn’t get vaccinated, so he was replaced on the boat by keyboardist John “J.T.” Thomas’s son, John. Lee’s wife, Karen, got vaccinated only because she wanted to be on the ship. She was not happy about it and, in her cabin, proudly shows off her Trump bracelets and books she brought onboard about Anthony S. Fauci and Democratic fundraiser George Soros.

“I did a Johnson & Johnson and I can do some blood treatments with ozone to purify my blood later,” she says. “And hopefully that will take me back to where I was before I had the vaccine.”

Then there was the case of Texas singer Dale Watson, an Outlaw Cruise regular. In December, he announced on social media why he wouldn’t be going. He felt he already had natural immunity and pledged to take a test before every gig, but “that’s not enough for this administration.”

Reached by phone after the cruise, Watson says he wasn’t sorry he missed out.

“It was totally Norwegian Cruise Lines, and they have to do what they think is best, but the Outlaw Cruise got stuck in the middle of that,” he says, and pauses. “It didn’t feel very outlaw to do something because you’re made to do it.”

The Waco Brothers, started in Chicago in 1994, have never been chartbusters. And though the band will throw an amped-up George Jones or Johnny Cash song into the set, it’s mainly country in spirit. The band sings of union workers and environmental disaster and are led by Jon Langford, a punk prankster who delivers jagged guitar lines on his sea-green Stratocaster.

It’s playing the final set on the pool deck. The week has been almost flawless, though the Beat Farmer’s bassist had to stay in his cabin after coming down with the flu, and a drunk cruiser did take a header on the floor by the Atrium bar during Bill Kirchen’s set. But that’s barely a blip on a boat occupied by so many.

Langford wears a Waco Brothers sailor hat, has Kantor play the set and calls up Sally Timms, his Mekons partner, for a few songs. (She was one of Tepper’s late, unbilled invites.) He also asks Shinyribs singers Alice Spencer and Courtney Santana to hop onstage.

Two years ago, before the shutdown, Langford and the Wacos took the pool deck with Lee “Scratch” Perry for Jimmy Cliff’s “The Harder They Come.”

“Probably the best night of my entire life,” Langford tells the crowd.

Perry died last year, but Langford, as a kind of informal tribute, decides to do the song again. He calls for Texas legend Joe “King” Carrasco to come to the stage.

“Where’s Joe the King? Release the King!”

Crowell, wearing a dark blue T-shirt and checkered Vans, leans against a post to the side of the stage. He spent last year feeling conflicted about his decision to tour behind a new album. He wore a mask and, as soon as he could, got vaccinated. But was his album promotion somehow contributing to the spread?

On this cruise, he has played gigs, been celebrated with a special tribute, and performed with friends Harris and Lee in the “Hot Band.” On the boat, Crowell talks of trying to be more understanding of differing viewpoints. The vaccine doubters got under his skin.

“And no, I don’t want them on a boat with me in the middle of Belize,” he said. “But I’ve grown weary of us and them.”

Even here, among the vaccinated, there are probably people who don’t share his political views. So what? After a few days at sea, with nobody arguing and a fully vaccinated crowd thrilled to be seemingly free to laugh and dance, Crowell has begun to think of the cruise as more than a paycheck. Maybe it’s part of how we move forward.

“Music has always had a transcendent function,” he says. “And that’s one of the things that are brought on this boat. I’m going to let go and I want to let go of this divide that I see because somewhere we’ve got to find some unity.”

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