Then there was his subsequent album, 2016’s This Unruly Mess I’ve Made, with producer Ryan Lewis once again riding shotgun. Featuring rap pioneers Melle Mel, Kool Moe Dee, and Grandmaster Caz, as well as up-and-coming stars like singers Anderson .Paak, Jamila Woods, and Leon Bridges, Unruly Mess was an aptly titled collection of half-baked wokeness meant to show listeners that Macklemore really did belong in hip-hop culture. Compared with The Heist, which sold millions of records and pushed him to meteoric heights, Unruly Mess was a critical and commercial failure, and—without explanation—Macklemore and Lewis didn’t submit it for Grammy consideration. A year later, Macklemore quietly released another album, Gemini, this time without Lewis as his producer. That album was far less political than anything he’d released. “I think it’s mostly the music that I wanted to hear,” the rapper told Rolling Stone. “I believe that music can be a form of resistance without having to hit the nail on the head in terms of subject matter. It can be something that uplifts, that makes you dance, that makes you cry, that makes you think.” Nowadays, Macklemore still tours, playing to thousands of fans in packed arenas, even if his star has dissipated in the States.
Meanwhile, following the 2014 Grammys, Kendrick traveled to South Africa to play a series of shows. The perspective he’d gain from the Motherland would prove invaluable for himself, the rap community, and the world at large.
For eighteen years, Nelson Mandela sat on a remote island in the middle of the sea. It was here—Robben Island in South Africa’s Table Bay—where the activist pounded rocks into gravel and wrote letters to his wife, close confidants, and children.
From afar, the island looked inviting, a secluded peninsula surrounded by crisp blue water. “It’s a very poignant place to be, because you can see South Africa, but you really can’t get there,” says Teresa Ann Barnes, an African studies professor at the University of Illinois who lived in South Africa when Mandela was freed from prison. Walking the land was something different: the struggle was baked into it; the souls of political prisoners loomed heavily above the threatening brick walls and looping barbwire. Robben Island was, in a word, hell, but Mandela—the South African philanthropist who was arrested and sentenced to life in prison in 1964—used peace as a weapon against daily hardship. He was a fighter who battled injustice of all sorts, whether it was the inhumane system of apartheid, or the censorship of his fellow inmates on the island. Mandela was a leader with incredible resolve, and though he spent twenty-seven years in prison, his thoughts remained with the oppressed people back on the mainland. The resistance sustained his spirit and kept him mentally sharp in his loneliest moments. He was the ultimate commander and parent, however tough it was to be those things from the isolation of a tiny cell. “Fight on!” Mandela once wrote in a statement made public by the African National Congress in 1980. “Between the anvil of united mass action and the hammer of the armed struggle we shall crush apartheid!” Apartheid would not be abolished until 1994, but anecdotes like these explain how Mandela became Mandela: he was just a man, but he cared most about the challenges beyond his immediate gaze. His aim was to unify communities, whether blacks and whites in South Africa or inmates and overseers in prison. He wanted to build a resonant voice that would influence equally resonant voices in the future. Nowadays, Robben Island is preserved as a monument to the friction endured by its prisoners, but it’s also a testament to the resolve of a person who’d rise from the shackles of oppression to mend a country wading through the uncertainty of life after apartheid.
Kendrick visited Robben Island in the winter of 2014, not long after the now-infamous Grammy Awards ceremony. He was in South Africa to play a trio of shows in Durban, Cape Town, and Johannesburg, and needed time away from the music industry machine to recharge and gain a new perspective. The trip was significant for Kendrick; he’d never been to Africa and wanted to absorb the culture for himself and his friends back home in Compton—roughly 9,960 miles away. “This is a place that we, in urban communities, never dream of,” Kendrick told comedian Dave Chappelle in a 2017 discussion for Interview. “We never dream of Africa. You feel it as soon as you touch down.”
Chappelle knew this pilgrimage: In 2005, he had left his highly popular Chappelle’s Show while filming episodes for its third season and traveled to Durban to visit his friend Salim. He, too, had needed to replenish his spirit: the false rumors claimed he was on crack cocaine, had a meltdown, and checked himself into a mental health facility. It was also said that Chappelle, a black man from the Washington, D.C., suburbs, didn’t like the way that white people laughed at his particular brand of comedy, which used sharp race-centered parody to mock cultural stereotypes. It was like they were laughing at him, not with him, and thus the heart of his show had lost its beat. Couple that with the trappings of newfound fame; Chappelle had inked a $50 million deal ahead of the season’s production, and—as he told Time two weeks after walking away from the show—certain people within his inner circle had begun to change. “If you don’t have the right people around you and you’re moving at a million miles an hour you can lose yourself,” he told the magazine. By the time he got to South Africa, he was stressed and needed new creative energy.
The same went for Kendrick; by the time he got to South Africa in early 2014, his fame was still relatively new. In the U.S., good kid, m.A.A.d city had sold more
