Ray Wylie Hubbard's 2020 collaborations album, Co-Starring, was a testament to the weight his name carries in the country music community; the album's successor, Co-Starring Two, only underscores the point.

"I feel so very fortunate and grateful to even know these people," Hubbard professes to The Boot, offering a specific example in the form of Wynonna Judd, who lends her vocals to one of the album's marquee tracks, "Pretty Reckless."

"I said, 'Would you sing on this song?' She goes, 'Sure.' I go, 'Well, do you wanna hear it [before you say yes]?' She goes, 'No, I trust ya,'" he recounts. He'd first gotten to know Judd at one of his shows in Nashville. He heard a big, booming, familiar laugh, looked up, and there she was sitting in the balcony. Ever since then, they'd kept in touch, but he never expected her to sign on to a duet sight unseen.

"And that just validates me somehow," Hubbard adds. "All this old road dog stuff. It's worth it, just to have somebody of that caliber be a part of it."

It's easy to see why musicians of every corner of the genre -- and beyond -- would be filing up to put their name next to Hubbard's on a project. A venerated Texas Heritage Songwriters' Hall of Famer known best for his gruff, acerbic pen on songs like Jerry Jeff Walker's "Redneck Mother," Hubbard became a sherpa for a whole new generation of country outsiders when he co-wrote Eric Church's 2018 hit, "Desperate Man."

A new version of "Desperate Man," featuring the Band of Heathens, makes its appearance on Co-Starring Too, stripped down to what Hubbard describes as a "roots thing." He patterned it after the kind of music he likes to listen to: Real and raw, with minimal overdubbing and a spotlight on the instruments being played. Hubbard name-checks some of his favorite rock 'n' roll records as influences for his recording process, adding that the guitars were tuned to the piano, "just a smidgeon, just enough to make it cool."

Hubbard's always had something of a rock 'n' roll vision. More than ever, that aspect of his musicality gets the spotlight on Co-Starring Too, especially in songs like "Texas Wild Side," "Naturally Wild" and "Only a Fool."

But, crucially, Co-Starring Too isn't only about Hubbard's vision. It's a true collaborations project, and he offers ownership to his duet partners at every turn. "Hellbent for Leather," a duet with Steve Earle, is at least in part an homage to everything Hubbard loves about Earle's own musical style.

"The song was gonna start off with kind of an acoustic bluegrass riff, and I love Steve's album he did with Del McCoury -- it's just such a terrific record. But Steve also has that full-tilt rock 'n' roll Dukes attitude," he explains. "So I said, 'Pat, I need you to put some teenage caveman drums on it. Like a kid got a drumset for Christmas. That's what we want in there, put drums on it, because it's Steve, and I so admire his rock stuff he does."

On other songs, he captured the attitude of his guest artists, too. "Fancy Boys," a track that bemoans country music's turn towards poppier stylings, finds Hubbard at his grouchiest; therefore he called up three of the most cantankerous traditionalists he knows: James McMurtry, Hayes Carll and Dalton Domino.

"Because those guys are just ornery. They're like Waylon [Jennings]. Ornery, lonesome and mean," Hubbard continues.

The song was a solo write for Hubbard. "There was all this controversy about 'bro country,' and...I was just thinking about the whole thing, how that really isn't country music," he says. "I hate to be the old guy sitting out in the front yard, yelling 'You kids get off my lawn,' but to me, country music is of course Lefty Frizzell, Willie [Nelson], Waylon, John Anderson. I started thinking about these kinda guys, that are on a stage where Waylon once stood, and I got to get my digs in, a little bit. Some of these guys are just kinda doing dance moves."

His lyrics are cutting -- "Willie said roll him up and smoke him, it'd be easier with a bong / Just throw my ashes in the face of whoever's got this week's No. 1 country song," he sings in the final verse. But Hubbard's still plenty self-aware, and his kindness still shines through, even when he's talking about some of his bleaker opinions on country music's new crop.

"When we're finished here, I'm going to go out to the yard to yell at clouds," he jokes.

The oldest song on Co-Starring Too is four decades old, and it's "Stone Blind Horses," a song that Hubbard imagined Willie Nelson's voice on back when he first wrote it. Now, that dream is a reality. "I think we went through Willie's management, called them up and said, 'I have this song that Willie would be great on, and I'd love to have him be a part of it...Willie said, 'Oh, I'll sing whatever he wants me to sing.' So we sent the song, and he loved it," Hubbard remembers.

That running theme of artists saying yes to a duet with Hubbard, even before they've heard the song in question, dominates the track list of Co-Starring Too.

"I'm fortunate and grateful that that's where I am with this record," the singer acknowledges. He's quick to pass the credit to his wife Judy, who runs Wylieworld Music, LLC, the parent company of his publishing catalog and other facets of his career.

"I'm very fortunate, too, that I sleep with the president of my publishing company. That's a good place as a writer, because Judy will say, 'You write the songs you wanna write, you make the record you wanna make, and I'll try to sell the damn things," he says. "I tell people, if it wasn't for Judy, I would have everything I own in a shoebox, because she really makes it work. As a writer, I have the freedom to write about what I wanna write about."

Creative freedom and talent go a long way towards longevity, but to assemble the kind of all-star guest list featured on the Co-Starring projects, you need grace and generosity of spirit. Hubbard's got both. His kindness and care for his duet partners is what keeps them signing on to sing with him, and it's what is allowing him to continue to amass more duets. When asked if there's a Co-Starring Three in the offing, Hubbard replies with enthusiasm.

"Yeah, I got seven done. Seven that are done with certain people," he relates. "Seven done, and I got a bunch more on the cutting room floor. So to answer your question -- maybe so, yeah."

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