Travelling together: Jesse Clegg and Msaki collaborated on Entropy, which is due to be released in January. Photo: Marty Bleazard
When Msaki met Jesse Clegg in June 2022, she didn’t know she was meeting a friend who would help shape the next three years of her creative journey.
What began as a simple meeting to reimagine some of Johnny Clegg’s classic songs has evolved into Entropy, a six-track EP alchemised from friendship, curiosity and an almost accidental artistic chemistry.
Both Msaki and Clegg are musical forces in their own right.
Msaki, the genre-bending composer and singer-songwriter from East London, has spent over a decade crafting some of South Africa’s most soulful and compelling music, from her debut EP Nal’ Ithemba (2013) to the South African Music Award-nominated Zaneliza: How The Water Moves (2016).
Clegg, a platinum-selling artist and multiple South African Music Awards nominee, has carried his late father’s torch of cross-cultural storytelling into the modern era, producing chart-topping singles and albums like Life on Mars (2011) and Things Unseen (2016), while collaborating with Grammy-winning producers in Los Angeles and New York.
So when these two powerhouse musicians first crossed paths, it was inevitable that sparks would fly, just not in the way either expected.
“I remember when we met,” Msaki recalls. “It was around mid to end June 2022. Jesse reached out saying he was reimagining his dad’s music and thought my sound would make sense for that idea.
“We spoke on the phone and met the next day. He pitched up at my house and it feels like we’ve been friends ever since.”
Their first collaboration was Hoping for a Miracle, a song that fused Johnny Clegg’s classics into a tribute performance.
“That’s kind of how we became friends,” she says simply.
From there, the two found themselves in each other’s orbit, sometimes halfway across the world, creating music neither had planned to make.
“Me and Msaki met each other at a very specific time in both our lives,” Clegg explains. “We were going through different kinds of challenges and there was a lot that we resonated with, personally and artistically.
“The album is kind of a snapshot of that time. We didn’t sit down and say, ‘Let’s make an album.’ It just happened to us.”
And “happened” might be the best word for it. Over three years, the pair recorded across continents — in Cape Town, Johannesburg, Los Angeles and New York — with songs taking shape in fragments before being completed elsewhere.
“Wayside Lover started in LA, continued in Joburg and finished in Cape Town,” Clegg says.
“Some songs existed in multiple studios and countries. The space and energy of each place influenced the music. That’s why it feels like a reflection of that period, geographically and emotionally.”
That effortless flow is what gave Entropy its name.
“In science, entropy is the tendency of a system to break down, to self-destruct,” Msaki explains.
“It’s about accepting that decay and asking: ‘Do you see beauty in that? Do you fight it or do you let it be?’ It’s sad, but also natural. Things fall apart but that’s part of life.”
“And the act of creation,” Clegg adds, “is a defiance of that decay. The joy of life is to make something despite entropy; to connect, to create, to fight against the natural order that everything falls apart.”
It’s this dance between connection and loss, tension and release, that runs through the EP’s first single Wayside Lover, a haunting collaboration with Sjava that debuted last month.
“That song was chaos,” Clegg laughs. “We’d just come back from Coachella — dehydrated, hungover, half-dead — and started writing the next day in LA. My friend Nick Petricca laid down some piano and drums and then we sat outside piecing lyrics together in that delirious haze. But somehow, out of that chaos, something true emerged.”
Thematically, Wayside Lover explores love’s near-misses and the bittersweet art of letting go — a motif that runs through the rest of the EP.
Sjava’s verse, Clegg says, was an unexpected gift: “I played him the song while we were working on something else and he just said, ‘I want to do a verse on this.’
“It was a beautiful contribution from one of our favourite artists.”
For Msaki, the organic evolution of the music mirrors her creative philosophy — that art is best born from friendship, not formality.
“The way that we spend time together, the byproduct of that is music,” she says. “I often experience music as a byproduct of friendship. That’s how this happened.”
Their collaboration will take the stage for the first time on 19 October at the Walter Sisulu botanical gardens in Johannesburg, where they plan to debut material from Entropy ahead of its full release in January. The timing, Msaki insists, is deliberate.
“We could drop the album right now,” she laughs. “But we wanted a quiet moment for it. January feels right. People are a little more introspective, maybe a little broke, ready for a complicated story.
“We also want to give people time to understand the collaboration, the ‘how’ and ‘why’ of it.”
Between now and January, fans can expect another single, How Dare You, and a series of music videos that tell a story across six tracks.
“We’ve shot a video for every song,” Clegg says. “They form one narrative — a kind of tragic love story, like Bonnie and Clyde — set across South Africa. The first one starts at Chapter Four, so people will be a bit disoriented at first, but it’s all breadcrumbs leading to the full reveal in January.”
If the music emerged effortlessly, the collaboration itself was a study in balance.
“I’m very meticulous,” Clegg admits. “I’ll mix a song 55 times and drive my manager mad. Working with Msaki taught me to trust instinct — to feel rather than overthink.
“She has this deep sense of what the song is and whether a detail actually serves its truth or just makes it sound prettier. That’s been a big lesson for me.”
Msaki smiles when she hears this.
“To his credit, he’s done really well at letting go,” she says. “And I’ve also learned from him. I come from this very live, old-school approach; three takes and you’re done.
“But when it comes to details that affect emotion, I lean on his ear. There’s been a real cross-pollination of method and a bit of madness too.”
That mutual respect extends to their shared love of songwriting.
“Jesse’s a brilliant songwriter,” Msaki says. “He’s intentional, poetic, always thinking about how to tell the story better. It’s rare to find someone who geeks out over songwriting like I do. That’s been one of the strongest connection points between us.”
They also discovered that both were chasing similar dreams abroad, immersing themselves in songwriting cultures in LA and New York, where collaboration is part of the rhythm of the cities.
“We’re both serious about growing as songwriters,” Msaki says.
“In LA, there’s a system for that you can meet a new producer every day and walk away with a new song. I’d love for that kind of infrastructure to exist here. But for now, that’s where some of the best collaborators are: in LA, Nashville, Sweden. It’s part of growing.”
The result of all this cross-pollination is an album that feels neither like a “Jesse Clegg” record nor a “Msaki” one — but something new, something that could have belonged to an entirely different artist.
“When we had the first two songs — Untimely Disclosure and Wayside Lover — I remember thinking, ‘This doesn’t sound like me or Msaki. It sounds like something new,’” Clegg says. “It wasn’t me featuring on her song or her featuring on mine. It was its own world. That’s when I knew we were onto something.”
Msaki agrees: “At some point I realised that this project was letting us go places we couldn’t go alone — emotionally and artistically.
“It needed its own space. It’s a testament to what happens when there’s friendship and safety. You can go deeper.”
For Clegg, the process has echoes of another iconic partnership — his father Johnny’s legendary collaboration with Sipho Mchunu in Juluka.
“I think of my dad and Sipho,” he says. “Their friendship created something greater than either could have made alone — something culturally transformative.
“In a different way, I think that’s what this project is about too — friendship giving rise to great art.”
And perhaps that’s the most fitting description of Entropy — a beautiful defiance against decay, a collection of songs that grew quietly from friendship into art. Or, as Msaki puts it: “We didn’t plan it. We just followed the music — and it led us here.”
• Msaki and Jesse Clegg will perform music from their EP Entropy on 19 October at the Walter Sisulu National Botanical Garden in Johannesburg. The full EP is scheduled for release in January.