After hearing Elizabeth Cook and her aces three-piece backing band Gravy (guitarist Andrew Leahey, bassist Steve Duerst, drummer Herschel Van Dyke) play some of the new material on her upcoming album, its still yet-to-be-announced release can’t get here soon enough. Greasy rumblers like “Thick Georgia Woman” and “Bones” were well-suited for a boat full of outlaws, with Cook, in her dynamite fringe jumpsuit, cutting the most outlaw figure of all. The high point, though, was her reading of the new waltzing, classic-country song “Two Chords and a Lie,” a phrase that feels way more relevant today than the one that inspired it.

Chicago by way of Wales country-punk Jon Langford led the rowdiest group aboard the ship, the Waco Brothers. Whether they were playing a small interior stage or high-kicking their way across the pool deck (with guest Lee “Scratch” Perry, no less), Langford’s twang-rock band of brothers were mesmerizing. Evoking the best and baddest sides of the Clash and Johnny Cash, the Wacos steamrolled through shout-alongs like “Building Our Own Prison,” “Going Down in History,” and a cover of “I Fought the Law.” Both political and celebratory, the Wacos are essential listening for our current conflicted moment.

Lucinda Williams just announced her new album Good Souls Better Angels, due in April, but on the Outlaw Country Cruise she was already playing songs off the rock-forward LP, like the Trump-eviscerating “Man Without a Soul.” The biting, fresh material clearly invigorated Williams, who was as energized onstage as she’s been in years, even when tearing through live-show staples like “Joy” off her iconic Car Wheels on a Gravel Road album. 1989’s “Changed the Locks,” in particular, was a revelation, a combustive mix of Williams’ droning vocals and the stomp and grind of her band Buick 6. Williams, who recently turned 67, looks and sounds reborn.

Sixthman and the Outlaw Country folks know how to curate a guitar pull. No less than four writers rounds were held over the course of the voyage, with artists like Jon Langford, Laura Cantrell, Jesse Dayton, Ted Russell Kamp, and Jesse Malin all trading songs. The final assembly was worth the price of the cruise alone: Steve Earle, Lucinda Williams, the Mavericks’ Raul Malo, and Son Volt’s Jay Farrar all sharing the same stage. An Americana outlaw’s dream.

Carlene Carter brought along her trusty autoharp and a catalog of songs to the boat, carrying on the legacy of the Carter Family with inspired, folksy performances. She also sat with Sirius XM Outlaw Country host Elizabeth Cook for a candid Q&A, in which she talked about growing up the daughter of June Carter and Carl Smith, and the stepdaughter of the man she called “Big John” (that’s Johnny Cash, to you and me). Carter even guided a field trip to Johnny and June’s vacation home, Cinnamon Hill, in Jamaica, leading a group that included Kris Kristofferson in a sing-along of “Will the Circle Be Unbroken.”

Kris Kristofferson was the legend-in-residence on OCC5, joining Merle Haggard’s band the Strangers to deliver a knockout set of country classics. He didn’t just lean on the hits either: along with the ubiquitous “Me and Bobby McGee,” the 83-year-old Kristofferson offered a stark reading of 1970’s album track “Darby’s Castle.” He was also the subject of an all-star tribute concert from writers he’s influenced like Lucinda Williams, Shooter Jennings, and Steve Earle — whose onboard songwriting workshop, Camp Copperhead, Kristofferson attended to fine-tune some song ideas.

Jesse Malin’s Outlaw Cruise was his first cruise in general, but the New York sidewalk poet took to it like an old salt. Over two solo performances with his right-hand man Derek Cruz on piano and guitar, Malin played songs off his Lucinda Williams-produced album Sunset Kids and told wry, often self-deprecating tales of life as an aging punk. The cruise crowd, many of whom hadn’t heard Malin before, ate it up, especially when he guested with Williams on the pool deck to sing their blistering collab “Dead On” and a defiant rendition of Neil Young’s “Rockin’ in the Free World.”

As soon as the reggae and dub music living legend hopped on the boat in Falmouth, Jamaica, Lee “Scratch” Perry was turning heads. Dressed in loud colors with a red beard and carrying a phone and a lighter, he hung with Kris Kristofferson, led a painting demonstration for cruisers, and hopped onstage with artists like Waco Brothers and Jesse Dayton to re-create the classics “War ina Babylon” and “Police and Thieves.” At one point onstage, he flicked his lighter’s flame directly into his microphone, proof that, even at 83, the producer of Bob Marley and the Clash is always searching for fresh effects.

On last year’s Outlaw Country Cruise, Jesse Dayton was bringing his brand of crunchy guitar-rock and winking lyricism to the smaller stages of the boat. This time, the outspoken Texas songwriter packed the vessel’s largest venue, the Stardust Theater, for a rip-roaring night of covers off 2019’s Mixtape Volume 1 project and fan favorite originals like “Possum Ran Over My Grave” and “Daddy Was a Badass.” Dayton is a wild live performer, slashing at his guitar like a serial killer, and he’s just as impassioned of a raconteur — at one point imploring his audience to not judge Jamaica by its sanitized, tourist ports. “Go to the cliffs of Negril,” he said, “It’s fucking paradise, man.”

After midnight, the Norwegian Pearl’s casino becomes the epicenter of the boat, with artists and cruisers mingling, gambling, and drinking. And the late-night DJ sets provide the ideal soundtrack. This year’s stop in Falmouth, Jamaica, allowed guest DJ Jesse Malin to lean hard into a theme of reggae and punk, a combo that was all but perfected by the Clash. Shooter Jennings, meanwhile, dug into an eclectic, inspired mix of country and experimental music, making the case that the Grammy-winning producer’s natural state may be in front of the laptop.