How Msaki and Jesse Clegg Found Trust in the Middle of Grief

Msaki and Jesse Clegg have had a packed week. In addition to fulfilling duties for their solo work, there’s the not-so-little news of the short film for their collaborative EP, Entropy, finally releasing to the public in its entirety, after living as fragments on YouTube, starting with the Sjava-featuring “Wayside Lover” in October last year, and concluding with “Awake In The Nighttime” as March got in motion.

The week also saw them announce the Scatterlings Festival, named after Clegg’s father, Johnny, whose imprint on South African music — first as one half of the duo Juluka alongside Sipho Mcunu, then as a solo artist — remains a masterclass in how to build and sustain a career. The festival will feature friends and close collaborators, from Zakes Bantwini to Zolani Mahola to Simmy, Jabulile Majola and more. It will be held in Johannesburg on August 1st, and it’s something the younger Clegg admires about their collaboration.

“We have a very productive partnership. In the short four years that we’ve known each other, we’ve launched an album, launched a short film,” he says, while Msaki adds, “and A&R’d an album with four other artists that are our friends, trying to manage the creative process of other artists and be there for them.”

We speak on a Saturday morning, which is unusual, but their schedules haven’t allowed for much free time. Msaki flies to Japan the following day, while Clegg is still recovering from playing one of South Africa’s longest-running music festivals, Splashy Fen, and preparing for a trip to New York later in the month. 

The two met in 2022, during tectonic shifts that reconfigured their worlds and, in a way, changed their modalities of operation. It was the year Msaki announced her hiatus from music, while navigating a divorce; and the year Clegg lost his wife to cancer, leaving him the sole carer of an 8 month-old baby. It was a time of heavy loads and difficult decisions, but also an opportunity to begin anew, a window to imagine a different outcome.

Entropy — a scientific concept meaning a measure of disorder or randomness in a system (a tidy room has low entropy, one specific arrangement; a messy room has high entropy, countless ways to be messy) — felt fitting for the decay they were both experiencing: having to exist as public-facing individuals while chaos unfolded in very intimate corners of their lives.

The six songs on the EP took three years to shape. They developed a life of their own across Johannesburg and Cape Town and New York and Los Angeles — in between studio work and festival performances and tribute shows; in between school runs and visits to the jungle gym; in between trying to keep it together in a world that is going to shit. The material comprising the album is anything but in-between.

We speak at length about their creative approach, their songwriting chops, the care and commitment they lend toward creating something grand and all-encompassing — entirely removed from their individual sonic identities, yet reflective of a specific time and feeling. Can they hear the imprint of that time with the benefit of hindsight, OkayAfrica wonders.

“It’s like the universe reveals people to you in the moments in life when you’re meant to meet those people. Meeting someone who was also facing loss, someone who is a parent in the music industry—which felt absolutely terrifying to me, especially by myself; someone I respected as a songwriter, as an artist, and someone who’d held a cultural space in South Africa that resonated with me, that reminded me of my dad in a way,” says Clegg.

“This album, for me personally, was a quiet space to sit with a friend and reflect on loss: on how to hold hope, and how to allow new connections and new relationships into your life. How do we let go and still hold on to the things that make us who we are?”

It’s a vulnerable snapshot into attempts at rebuilding, held through the trembling hands of people learning how to walk again, made possible by a world of collaborators who believed in the work and saw it through. But what does newness look like when one is trudging through the shadows? How does one imagine newness in the midst of earth-shattering, body-dissolving, rapturous pain?

“I don’t understand the timing of how and why things happen, either. But I did meet Jesse, and it instantly felt like family, and I was very trusting of that from the get-go. It was also things like, you meet someone, and then you realize they live seven minutes away from you, around the corner. All of a sudden, it feels like they’ve always been there,” says Msaki.

“More than anything, it was an in-the-eye-of-the-storm kind of feeling. It’s not like life ceased to fall apart, but I think the blessing there was that the stillness came with a very profound connection — but also a place to create, when I felt betrayed by the place that I had put my faith in. So to me it was also like, I’m not really interested in the industry right now, but somehow there’s a tender space and a friendship that’s making me want to write. And I wasn’t really trying to be in the studio at the time.”

In using the city as its backdrop, the film doubles as a tale of two worlds, but also as a visual anthology of its many corners: the shifting shapes, textures and contours that inform the pulse of inner-city and downtown Johannesburg, a city dealing with its own grief, assessing its own decay, measuring its disorder and randomness — against neglect, against people moving through it with reckless abandon; defending itself against being the primary target, the one to blame when those people fuck their own lives up.

The colours are warm, the angles wide — angels with wings watching over a city in constant motion. The actors, Ditebogo Mandita and Ally Damon, indeterminate love bugs with undetermined futures, guide us through this world: anchors in a maze, stripping away the confusion and re-centering the album’s emotional core through movement.

It’s in moments like Mandita saying, “I have a crazy idea. Let’s just leave this place,” during an outside scene set on Juta Street in Braamfontein — the culture capital of a city that has died a thousand deaths and come back more determined to live — that the conceptual treatise of the project links to its aural and visual embodiment.

There is, at once, a desire and a resolve: to leave the present, to become something else, to abandon the claustrophobic, messy city for the open country.

There’s also a scene at the famed Kwa Mai-Mai, located adjacent to the Maboneng Precinct, itself a symbol of what happens when a city’s natural process of decay gets glossed over and gentrified. Director Marty Bleazard imagines it differently from, say, hip-hop videos that show the place in its daylight glory, in all its braai-having, crowd-containing detail.

Here, warm colours contrast against cold, luminous tones that flushes the background. The detail of police sirens is not incidental; it’s how the city’s violence extends to the people who inhabit it, follows them indoors on their way from work, and keeps haunting them come sleep time.

So when Clegg sings, “Entropy / everything I ever wanted wasn’t meant to be / everything that I tried to build just fell apart,” on “Awake In The Nighttime,” it punctuates a scene, acknowledges an end, but understands that the conclusion is not pre-determined; that it’s still up to him to figure life out.

This interplay — between darkness and light, willing and unwilling — is one level that guides Entropy’s coherence. Another is a set of collaborators who, on some level, were able to connect so deeply, without hearing each other’s work, that they emerged with the same ‘80s aesthetic that shapes the project’s big, expansive sound. Peter Gabriel gets named, as does Kate Bush, as some of the album’s sonic ancestors, but only from a feel perspective.

“The production was decided on with different producers and different spaces. The coherence is almost accidental; because everybody’s doing their own thing in their own pockets,” says Msaki.

Clegg adds: “Also, the guy who mixed the album, Damian Taylor — he’s a student of the ‘80s, he was Björk’s keyboard player for a decade. He’s a noise-maker, a sample guy. He’s also produced some of my favourite contemporary bands —Temper Trap, The Killers, Arcade Fire. He’s got a very eclectic palate.”

“Jesse introduced us in L.A., and he’s probably one of the album’s biggest champions,” Msaki says.

In L.A., in Johannesburg, in Cape Town and New York, they tinkered on songs, geeked out over the songwriting process, their absolute favourite part of creation, and emerged with a cohesive, solid, representative body of work that is rooted and considered, crafted to exacting standards.

That "Wayside Lover" was chosen as the lead single was fitting, if anything for the lyric "are we trapped inside of Plato's cave/ .../ just dancing shadows to be named," which, even without the additional context of the Greek philosopher's allegory, still manages to stick. It set the tone, sounded the first note, and communicated that we're dealing with serious songwriters before us. 

Co-written with Petricca, its backstory starts at the tail-end of four days spent at Coachella. Regular Msaki collaborator Sun-El Musician was around, as was actress and television personality Pearl Thusi. "We went back to [Petrricus'] house, and it was our first moment of calm. He just started playing [the chords to the song], and the whole song was written that night," says Clegg. 

He goes on to explain the philosophy that underpins their process: "The great thing about the experience writing the album is that we're both very committed songwriters. We love melody, and we love lyrics, and playing in that world. I had the melody ("talking about a wayside lover, I wish you well"), and I felt that maybe it was a bridge or something, and Msaki was like, that's the chorus, but we're gonna change the timing. So she split the phrasing up. It's that back-and-forth; sometimes you're the soundboard to the other person, trying to pick up their ideas. Other times, you're coming up with something, and just throwing it into the mix, and they run with it. That was the funnest part of the whole experience—trying things." 

It's details like the Plato's cave reference that get Msaki excited to write songs. "[It's] just so nice to have someone to geek out with," she says. "[Jesse] is such a meticulous songwriter; he's doing zen on each line, on each rhyming phrase, on each metaphor. It's very refreshing. It's very challenging, as wel."

The lyrics on "Untimely Disclosure" hit different with the context of what she was going through. One almost wishes they were beside her when she sings, "sow up these fault lines, can these wounds disappear?/ where do we go from here?/ I'm not yours, you're not mine." It's rendered poetically, yet remains relatable; she mines the core of the matter and hands it to us unfiltered, guts and all. 

All of this collaborating, and opening oneself up in untested ways, requires a level of trust that is rare, especially in professional music industry circles.

“I guess it’s just showing up, whether you’re in your best form or not. It’s consistency, and being willing to — like any relationship — have ways to deal with good moments, and healthy ways to deal with not seeing things the same way. It’s interesting how the creative process catapults you into a masterclass in how to navigate that within two people’s dynamic. The creative process will show you the difficulties very fast, and how you solve those conflicts," says Msaki. 

“We’ve also had real-life testing, in how we solve conflicts and how we handle moments of highs and lows. The ease is still there, even though life is not easy. We’re still figuring out what our dynamic is. I guess that’s the blessing, there’s definitely something to preserve. There’s a friendship, there’s a human that I care about, there’s a person that holistically matters to me, not just because we’re trying to finish an album,” she concludes.