There were many contemporary western musicians who performed with South African artists, especially as Apartheid was winding down in the late 1980s.
But musicians like Paul Simon and Peter Gabriel never went to jail for playing with those artists. Johnny Clegg did. Clegg moved to South Africa as a boy in the late 1960s and was attracted to the culture and tunes of Zulu street musicians in Johannesburg. That was not legal in those days, but it didn’t deter him.
"I was totally curious and fascinated and wanted to learn it...I was shifted into a completely different world and reality," says Clegg.
Immersed in the hidden world of the Zulu migrant laborer, his early life and teens was infused with Zulu war dancing, fighting, praise poetry, language, and rhythms. However, even at a time when white kids didn't do those things - legally - Clegg didn't see his actions and arrests as particularly brave. "I was not a politically conscious adolescent. I did this through the love of the music and the language," he explains.
Zulu culture, Clegg explains, offered him a way to identify with the place he was living, but it was when he went to university when he began to view Apartheid differently. "I came to question why was my behavior being criminalized? Why did I always feel like I had to be a ghost getting from one place to another?" Clegg recalls.
In the 1970s, Clegg and Sipho Mchunu formed the band Juluka, which attracted both black and white audiences, and also the unwanted attention of security forces.
Clegg’s music became, in part, a symbol of what could be in South Africa, and it outlasted Apartheid.
In the mid-80s, Clegg wrote a song, "Asimbonanga," in honor of the then-jailed Nelson Mandela. He was performing it in 1997 when Mandela joined him.
"Who’d ever imagine that 11 years later, he would walk on stage and sing along with me? The universe is such a strange place. And it’s the pinnacle - as a singer-songwriter, that’s finest moment of my life."
Clegg says that Mandela had a true gift of communication. "He had that incredibly civilized and formal internal composure and he had a remarkable ability to listen and make you feel like you were the only thing in his universe at that moment."
South Africa is far from over the racial issues that has plagued its history, but Clegg sees their current issues much like the events and identity politics happening in the rest of the world.
"We're in a pretty touchy moment in South Africa, but if you look at Catalonia in Spain, if you look at Brexit, if you look at Donald Trump's appeal to people's sensibilities about how America has been sacrificed on the altar of globalization - this is a common theme that's running through many places," he notes.
What the future will hold for Clegg is potentially scary as well. For the past several years, he's battled cancer that has required several surgeries. The disease is currently in remission, but for how long is unclear.
But just as Mandela said music and dancing made him at peace with the world, Clegg continues to carry that message. "When I perform, I'm connected to my past, my present, and my future. And I bring with me a deep desire to connect with my audience in that moment," he says. "This particular show is really a kind of wrap up of my 40 years of music."
Clegg will play a concert at Park West in Chicago on Sunday as part of his farewell tour. His new album, King of Time, came out Friday.