Matt Sweeney and Will Oldham are two of indie music’s greatest collaborators. For proof, just listen through the two 51-year-olds’ recent discographies, the latest chapters in each artist’s decades-long history of playing well with others. In particular, make time for the new album they’re about to release together, as brilliant a collection of songs as any these two have ever worked on.

Sweeney — an NYC-based guitar master who came to underground prominence fronting the cult-beloved Skunk in the ’80s and math-rock staples Chavez in the ’90s — helped fellow Matador Records veterans Kurt Vile and Stephen Malkmus get in touch with their rootsy sides on a pair of 2020 releases, Vile’s EP Speed, Sound, Lonely KV and the Pavement/Jicks leader’s album Traditional Techniques. Before that he worked with veteran Nashville recording engineer David Ferguson on music for the hit Western video game Red Dead Redemption 2. Clean cut and distinctly mustachioed, with the slim frame of a distance runner, Sweeney is so gregarious that he once hosted a talk show for Vice called Guitar Moves that consisted of shooting the shit and trading riffs with legendary players like J Mascis, St. Vincent, and Keith Richards. He is what happens when a guy who can’t stop collecting records also can’t stop collecting friends.

Oldham, the eccentric and robustly bearded Louisville singer-songwriter best known as Bonnie ‘Prince’ Billy, is more standoffish than Sweeney, but he clearly knows how to connect with kindred spirits. He just dropped a shapeshifting folk EP called Three Feral Pieces with Nathan Salsburg and Max Porter. He also spent a good chunk of the pandemic collaborating on covers with his legendary Drag City singer-songwriter peer Bill Callahan, with a rotating assortment of friends, tackling songs by Leonard Cohen, Billie Eilish, Steely Dan, and many more.

“We wanted to utilize our unique positions in life and music to occupy and preoccupy as many people as we could during the uncertainty and confusion of lockdown and distancing (including ourselves),” Oldham explained over email in the run-up to a Zoom conversation between Sweeney, Oldham, and me last month. “It was a fantasy idea, a shot at the moon, that couldn’t have happened in another time. I thrive on communication and community; that’s why I do what I do. We were essentially being advised to sacrifice or at least compromise those aspects of our lives. But we make records. We have friends who make records. We know what it is to communicate over time and distance and to use time and distance as strengths.” After confirming there are talks of combining the covers into a physical release, he continued, “As much as I take issues with social media and streaming musics, this series of collaborations was specifically designed to infiltrate the feeds and remind people of some of the truly cool shit that is not going to go away.”

More truly cool shit is imminent. Oldham and Sweeney have spent their whole lives engaging in fruitful collaborations — with Iggy Pop, Björk, Cat Power, Johnny Cash, Tortoise, Baby Dee, Andrew W.K., the Chicks, Charlie Louvin, Jim O’Rourke, El-P, and many more — but they may be at their best when teaming up with each other. This much was evident in 2005 when the duo joined forces for an album called Superwolf, an instant-classic pairing of Sweeney’s six-string prowess and Oldham’s surrealist warble. The friends’ superior chemistry is further confirmed on Superwolves, their first full-length collaboration since then, out next week on Drag City.

“It’s a given collaborator’s uniqueness that makes joining forces feel necessary in the first place,” Oldham emailed. “There are ways that Sweeney thinks and works, musics that he loves and audiences that he reaches, that I could never grasp on my own. And that’s the same for all of the successful collaborations I’ve been a part of, whether it’s with Meg Baird, or Dawn McCarthy, or Jacob Duncan. The other party must be similarly needy! And drawn to the idea of co-owning the task.”

With that in mind, both artists took the task of following up Superwolf very seriously, working in fits and starts over five years and never losing the thread no matter how many other commitments intervened. For two distinguished talents who’ve been tight bros since the late ’90s, the chance to surprise and inspire each other again was a labor of love, one the rest of the world now gets to benefit from. If it feels outrageous to suggest this latest LP is the best album either Sweeney or Oldham has ever worked on, it’s only because both of them have such stacked catalogs already. But please trust that Superwolves is a staggering achievement, one that will appeal to longtime fans and send newcomers scurrying to catch up on each man’s discography. Tender, virtuosic, and unpredictable, it is one of the most engrossing collections of music set for release this year.

Just as Aliens followed Alien, Superwolves is the sequel to Superwolf. But as with most epic franchises, there was plenty of story ahead of the first official installment. This saga’s Prometheus era dates back to 1980s Louisville. Oldham came of age with the members of the post-rock band Slint; among other points of intersection, he shot the cover photo for their landmark 1991 album Spiderland, an iconic portrait of the four band members neck-deep in quarry water. After Slint’s breakup, drummer Britt Walford relocated to New York, where he ended up sharing a Bowery loft with Sweeney. “Britt I’ve known since sixth grade,” Oldham said near the start of our Zoom call. “At one point, he was living in New York for eight years, and was icing X-rated cakes.” (“Very realistic X-rated cakes,” Sweeney added. “Veiny.”)

Oldham came to New York in 1998 to promote the following year’s I See A Darkness — his first release as Bonnie ‘Prince’ Billy after years spent recording under various permutations of the Palace name, and probably the most enthusiastically canonized album of his career. Walking down Houston Street one day during that trip, he spotted Sweeney and urgently flagged him down. The two musicians had become loosely acquainted through Walford, but on this occasion they were both eager to discuss some development in their social scene, “mutual friend stuff” they now deem too inconsequential to share. This encounter evolved into hours of conversation, forging a bond that has lasted nearly a quarter-century. “It turned out that the publicist that I hired was where Matt was working,” Oldham recalled. “We just then started to see each other all the time. All the boundaries dissolved.”

Within a week, this connection led to collaboration. The French film director Bertrand Bonello had commissioned Oldham to record a new song for his movie Quelque Chose d’Organique, which Oldham recruited Sweeney to play on. They headed to a studio belonging to German “techno god” Can Oral and cut their first song together, “What’s Wrong With A Zoo?” Not long after that they recorded two songs for the Sub Pop Singles Club. Sweeney soon began touring as part of Oldham’s band whenever available, and he played on Bonnie ‘Prince’ Billy’s 2001 LP Ease Down The Road. (So did film director Harmony Korine, a longtime friend of this crew who did the Superwolves cover art.) The partnership was interrupted when Billy Corgan — a passionate fan of Sweeney’s old band Skunk — invited Sweeney to join his new band Zwan in the wake of Smashing Pumpkins’ breakup. But when that ill-fated project flamed out two years later, Oldham invited Sweeney to accompany him onstage at a concert in London. “Then he sent me some lyrics and said, ‘How about you write some songs using these lyrics, and we’ll do those as part of the show?'” Sweeney remembered.

Sweeney had fronted bands and played sideman, but this was his first attempt to write music to someone else’s words. Inspired by Oldham’s brother Ned and his band the Anomoanon — whose catalog includes albums soundtracking Mother Goose rhymes and Robert Louis Stevenson poems among other prompts — Sweeney leapt at the challenge. Some of the songs he and Oldham wrote for that London show, including “What Are You?” and “Beast For Thee,” became the earliest additions to the Superwolf tracklist. “Will would send lyrics, I would make a rough recording, get together with Will somewhere like New Orleans or New York, and then we’d work out the tunes during the afternoon then go to whatever venue and play them in front of people,” Sweeney said. “That continues to be the process — a process I would recommend other people trying. It’s pretty fun.”

The songs they ended up with for Superwolf were surprisingly minimal but often unflinchingly raw, almost mythic in their allusions to wild animals and brutal physicality. They were folk songs, basically, but Sweeney played them with the spindly curiosity of a post-hardcore lifer raised on classic rock, threading them with arpeggios and surprising chord changes. On opener “My Home Is The Sea,” Oldham sang of wishing he was dead “in a shark’s mouth”; two songs later he promised “to take you over my knee and spank you mercilessly.” In her 8.4 Pitchfork review, Amanda Petrusich concluded, “Soft and subtle, Superwolf is the kind of record that unwinds slowly, and is best enjoyed over multiple listens and, unsurprisingly, many glasses of wine. Oldham and Sweeney mew coquettishly, stroking their guitars, cawing bizarre stories about love, death, and body parts: theirs is a rancid and beautiful landscape.”

They did not linger in that landscape for long. Although Superwolf was somewhat of an underground sensation at the time, its creators gave no interviews promoting the record, and after touring it throughout spring and summer 2005, both soon moved on to other projects. They kept up their long-distance friendship, though, and about five years ago Sweeney announced he was ready for Oldham to start sending him lyrics again. The ensuing era has been one of unprecedented stability for Sweeney. “I’ve been with the same person for five years who’s really supportive, and I don’t have any kids,” he said. “It’s been fairly chill, which helps in that it gave me a platform to be there for Will if need be.” Sweeney puts it that way because Oldham’s half-decade has been far more tumultuous, which contributed to the lengthy gestation process of this new album. “Not long after the earlier Superwolf record, my father died and my mother began showing signs of Alzheimer’s, all of which rocked my world,” Oldham wrote. “Then I met the person who would become my wife, and we had a child. My mother died in January last year. So if the lyrics lean towards the momentous, I came by it honestly.”

In our spoken conversation, Oldham reflected further on all that personal upheaval, sharing one of those simple yet deep observations that have always dotted his writing: “One thing that I recognized — developmentally, there was this strange crossover where my mother was getting more and more like an infant and my infant was becoming more and more like a person.” It was a harrowing experience, but he forced himself to find the positives in it. “Five or six years ago, she would do something or say something or react to something and I would think, ‘Well, on the bright side, it is kind of cool that I feel like I’m spending time with my mother’s four-year-old self,'” Oldham said. “First it was like her 12-year-old self, and by the end it was her one-month-old self. That is kind of amazing because I got this nurturing training prior to my daughter being born.”

On Superwolves, Oldham channels these experiences into some of his most vulnerable writing to date. Several songs explore the toil of protecting and preparing children, often interwoven with stories about suffering and death and God and reincarnation. There is foreboding; there is romance; there are popsicles. As ever, Oldham tackles each subject with a blend of grim straightforwardness and destabilizing whimsy. His words are sometimes too oblique or obviously character-driven to qualify as autobiography — and in the case of “Good To My Girls,” the story of a stoic provider who toughens themselves against love and hate alike, you could really read it either way. Yet even at his most cryptic — say, the climactic “God Is Waiting” lyric, “God can fuck herself/ And does, hardcore!” — the emotion animating these songs is searing and unmistakable. “I’ve come to discover that there is a kind of clarity in the lyrics I present to Matt,” Oldham wrote, “maybe a frankness that I avoid were I to be claiming something resembling sole responsibility for a completed song structure.”

Superwolves hangs together remarkably well even as it spans many moods, from its ominously swaggering dirge-rock opener “Make Worry For Me” (think Radiohead’s “A Wolf At The Door” from the wolf’s perspective) to “Resist The Urge,” a gentle bluegrass-tinted ballad in which Oldham promises to remain with his child even after he dies: “I’m in your breath, I’m in your hair/ I haven’t gone away.” Similarly warm and intimate is “My Blue Suit,” a love song only Will Oldham could write, built around the refrain, “You look better in my blue suit than I do.” Yet there are also full-blown rockers like “Hall Of Death,” one of three songs featuring Tuareg guitarist Mdou Moctar and his band, on which Oldham reels in the face of his mother’s deteriorating memory: “Every so often/ When the tide is low/ My heart starts to soften and cry: ‘You must go/ And give her your tribute’/ Though she don’t even know.”

Oldham strove to present a unified body of work — in this case one centered on familial love, grief, and perseverance. But the album owes much of its quality and cohesion to Sweeney. He has an uncanny ability to unlock new levels of depth and power in Oldham’s lyrics, often with lead guitar lines that practically duet with those trembling, careening vocals. Like Oldham’s meditations, Sweeney’s arrangements can be knotty with ideas yet streamlined for maximum impact. “I will, in my mind, have an idea of where a lyric could go, but I don’t waste any time telling Matt anything about where I think it could go because the fun is seeing where he thinks it should go, not where I think it should go,” Oldham said. Figuring out where it should go is never easy, though. “When you get an email, it’s always like, fuck!” Sweeney said. “It’s always, ‘Wow, this is awesome, fuck!’ That’s the deal pretty much every time. It’s never been like, ‘Oh cool, I know what to do here. It’s always a challenge.”

Beyond all that diligent tinkering, the same camaraderie that initiated the project was also the force that brought Superwolves to fruition. Sweeney became pals with Moctar’s bassist Mikey Coltun, which led to Sweeney and Oldham collaborating with Moctar’s band on a still-unreleased project. Those sessions inspired Oldham to get serious about finishing his new batch of songs with Sweeney. “It was like, when are they coming into the country next?” Oldham said. “When can we play with them again? Let’s have some songs for them.” Sweeney said hearing Oldham’s country croon over Moctar’s spiraling Tuareg guitar was satisfying, in part because it helped him draw new mental connections between disparate traditions. “Celtic stuff sounds African, and I’ve heard African stuff that sounds really Celtic. That’s all country,” he said with a laugh. “I was really excited that it’s also 21st century sounding — Tuareg music, but still music by a dude from Kentucky who grew up listening to country music.”

Speaking of country music, the two covers that round out the new album are oldies steeped in Southern tradition, and both were chosen because they found their way into team Superwolf’s nexus of friendship. Oldham introduced Sweeney to the traditional “I Am A Youth Inclined To Ramble” early on in their relationship; come Superwolves time, he suggested they cover the song they’d bonded over all those years ago. As for the other cover, Oldham and Sweeney’s friend David Ferguson — the Nashville veteran Sweeney teamed with for Red Dead Redemption 2 — put them on to the Gosdin Brothers’ 1968 country single “There Must Be A Someone.” As Sweeney explained it, “There’s this tradition with Ferg blowing our minds with songs,” dropping obscure gems into their group chat once or twice a year without context or warning. This one so captivated Sweeney and Oldham that they felt compelled to include it on the new album with Ferguson on standup bass.

For an album that often plays like mythology, there sure is a lot of history behind Superwolves. The album has been a long time coming, but after five years — or 16, or maybe 23 — it’s finally seeing release next Friday. The bulk of recording was completed just before the pandemic set in. Once COVID-19 sent the world into chaos, Sweeney and Oldham worked separately in Brooklyn and Nashville to finish up the album. It’s been done for a while at this point, but the collaboration continues: Note the Cat Stevens cover Sweeney and Oldham performed remotely last December, or Sweeney’s contribution to Oldham and Callahan’s quarantine version of “OD’d In Denver.”

Also still going strong is the group chat, a more ephemeral document of the community that undergirds those lengthy Discogs pages. “It’s a very diverse group of people who kind of all have a similar sensibility somehow,” Sweeney said. “It changes around.” Oldham said “a lot of male things” come up. “Many times Ferg will throw a thing in there and then there will be icy silence,” Sweeney recalled with a laugh. Recent discussion topics have included Hilaria Baldwin and, the week of our interview, Jimmy Fallon’s failed attempt to mock former Slint bassist Ethan Buckler’s band King Kong on The Tonight Show. “What a fuckin’ dork Jimmy Fallon is,” Sweeney said. “He exposed himself so hard on that one. That was discussed in the group chat.”

Superwolves is out 4/30 on Drag City. Pre-order it here.