Despite that process, some have criticized the academy for seeming out of touch with what’s really popular in modern music. They say voters don’t choose based on artistic merit, that they mark the same familiar names year after year. Still, that doesn’t explain why reggae icon Bob Marley and guitar god Jimi Hendrix never won Grammys at all, and why someone like Jay-Z has gone home without a trophy from time to time. In 2018, for instance, the rap mogul’s thirteenth studio album, 4:44, earned eight Grammy nominations, but he lost in every single category, including Album of the Year, Best Rap Album, and Record of the Year for “The Story of O.J.” The academy, he told Billboard, is “human like we are, and they are voting on things that they like. We can pretend we don’t care, but we do. We really care because we are seeing the most incredible artists stand on that stage, and we aspire to be that.” In an essay posted to Complex, music journalist Rob Kenner—a voting member of the academy—scrutinized the process, calling it disorganized. “Along with the official guidelines,” Kenner wrote, “I soon learned another unwritten rule during private conversations with other committee members: be careful about green-lighting an album by someone who was really famous if you don’t want to see that album win a Grammy. Because famous people tend to get more votes from clueless Academy members, regardless of the quality of their work.”
The Recording Academy established a private committee to scrutinize voter submissions after Lionel Richie’s Can’t Slow Down won Album of the Year over Bruce Springsteen’s Born in the U.S.A. and Prince’s Purple Rain in 1985. As cultural website Vox points out, “Richie was far from the best choice that year, and his win helped create the public perception that the Grammys were cut off from what ‘good music’ meant.” In Kenner’s essay, published before the 56th Annual Grammy Awards, he speculated about the likelihood of Macklemore and Ryan Lewis winning Best Rap Album over more deserving records like Kendrick’s good kid, m.A.A.d city. “Because of their tremendous commercial success and media exposure there’s a good chance they will win, despite the fact that most hip-hop aficionados would prefer to see the award go to pretty much anybody else—be it Kanye West, Jay-Z, Kendrick Lamar, or Drake,” he wrote.
In September 2018, in an attempt to resolve its long-standing struggles with diversity, the Recording Academy invited nine hundred music creators to join its ranks as voting members. The request, part of a recommendation earlier that year from the academy’s Task Force on Diversity and Inclusion, went out to producers, songwriters, instrumentalists, and vocalists who were women or people of color under the age of thirty-nine. The academy also diversified the composition of its nomination review committees, which determine the final Grammy nominations across categories. “We need a culture change overall,” task force chair Tina Tchen told Billboard. “We’re living through a moment where we’re seeing a national culture change on these issues. The music industry and Recording Academy are not immune to that.”
In the years since the 56th Annual Grammy Awards, the careers of Kendrick and Macklemore have gone in separate directions. In 2016, Macklemore released a song called “White Privilege II,” which, much like “White Privilege” in 2005, found the rapper addressing what other white people with similar platforms have largely failed to do: the fact that his skin color afforded him opportunities and safety that black people simply didn’t have. The song arrived at a time of heightened tension between blacks and whites: in the United States, unarmed minorities were being killed by mostly white police officers at an alarming rate, and anyone with a smartphone could see bullets penetrate black bodies on endless loop. It seemed Macklemore wanted to help the cause, to stand in solidarity with those who had lost loved ones and those who were tired of seeing their neighbors murdered without recourse. Yet as the song unfolded, “White Privilege II” became more about Macklemore’s own identity struggles and less about the people he wanted to support. In one moment, he wanted to march with those fighting the injustices; the next he was off to the side, wondering if he should have been there in the first place. Ultimately, the song raised questions about Macklemore’s authenticity and whether or not he should be inserting his voice into black issues. His perspective threatened to overshadow that of the activists on the ground doing the real work. Such was the dilemma of analyzing Macklemore: while he should have been commended for at least trying to address topics that other white celebrities wouldn’t touch, he ended up doing too much to show that he was down for the cause. It was not enough to be a good dude privately; he needed to show the world just how cool he was.
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 than one million copies—an actual platinum record. Toward the end of 2013, Kendrick had opened for Kanye West for a number of dates on his national Yeezus Tour. West was a dignitary at the time, and to open for him meant even greater exposure. Though Kendrick had spent the previous ten years releasing a number of mixtapes and independent albums—first on Konkrete Jungle Muzik, and then most notably on Top Dawg Entertainment (TDE)—he was, in the eyes of the public, still thought of as an overnight sensation. He wasn’t used to all this; he had always preferred to keep to himself in the background.
But now he was out front, and whether he liked it or not, success meant greater visibility, nonstop touring, and less time for himself. The album good kid wasn’t the only reason he was a star; a certain verse had something to do with that. In August 2013, Kendrick appeared on a track called “Control” with rapper Big Sean and spit a potent rhyme that called out nearly every MC who was popular at the time: J. Cole, Jay Electronica, Drake, Pusha T, and Meek Mill, among others. It was a bold move at a time when hip-hop wasn’t so bold; the diss resembled an action from the genre’s history, back when hip-hop was still finding its way, when Ice Cube tongue-lashed N.W.A, and KRS-One battled MC Shan about the best borough in New York City. The verse set off a firestorm: some felt attacked by Kendrick’s words; others applauded the tactic. “KENDRICK!!!!! Ohhhh Shiiitttttt,” Diddy tweeted. “I don’t feel like @kendricklamar dissed anybody,” rapper Trinidad James tweeted. “He just has moved up to another level.”
On the road, Kendrick would write rhymes on his phone and record music on a tour bus equipped with a mobile studio. These were less-than-ideal circumstances for his meticulous creative process, but for almost three years—including his own touring schedule before connecting with West—he had made the most of his time, pulling inspiration from the road. In December 2013, during a tour stop in Atlanta, Georgia, he found himself weighed down by his newfound prosperity. By then, he’d been on the road for four consecutive months, performing almost every night, aside from a few dates when Busta Rhymes, A Tribe Called Quest, and Pusha T opened for West instead. He was homesick and somewhat disillusioned by the massive universal impact of his music. Sure, listeners around the world connected with it, but did it have the same resonance in his hometown? Kendrick felt guilty for making it out when his friends—some of whom were talented musicians in their own right—were either in prison or gunned down. Three of his closest companions had been murdered between 2013 and 2014. He felt he needed to be home with his family and the loved ones of those who were lost.
Kendrick didn’t just want to be a voice of reason; he needed that voice to assuage this bout of survivor’s guilt. The shooting death of Chad Keaton—his friend’s little brother—hit him the hardest. On the evening of July 12, 2013, Keaton was walking down the road when a white sedan darted past him at the corner of Comstock Street and Parmelee Avenue. Shots rang out and wounded Keaton, who never recovered from his injuries. He died in the hospital thirty-one days later. Kendrick was close with Chad’s older brother, who was incarcerated and had asked Kendrick to make sure the younger sibling stayed on the right path. Chad was a good kid who had ended up in the wrong place at the wrong time. Ravaged by all the despair back home, Kendrick started screaming in his hotel room; later, he’d use the incident as the basis of a poem woven throughout his 2015 album, To Pimp a Butterfly. “It was something that just accumulated,” Kendrick told the Guardian at the time. “I was able to bottle that moment and put it on record.”
Despite his ascension, he rapped about depression and an inferiority complex. Compton—and Los Angeles as a whole—was chock-full of great lyricists with something viable to say, so what made Kendrick the one to rise above it all? It was a question with which he openly wrestled. “I find myself to be quite confident as a person,” he continued, “but you’re going to have that piece of doubt in the back of your head because we’re human.” Kendrick faced a great deal of pressure to top good kid, m.A.A.d city, a widely heralded classic that forced some to dub the young rapper the King of West Coast Rap. Mind you, Kendrick likely wasn’t thinking about that, or if he was, he wouldn’t say so publicly. For him, the art was first and foremost, and as long as his music came from an honest place, the accolades were a plus.
South Africa gave Kendrick a chance to reset and be one with his own thoughts. He went to the blighted neighborhoods away from the tourist-centric parts of Cape Town, Johannesburg, and Durban. He spent time with the children who actually lived there, using the trip as an opportunity to learn about the plight of their communities. His time on the continent set the foundation for Butterfly, a record that was as much about South Africa as it was about his own fight to deal with burgeoning fame. “I felt like I belonged in Africa,” Kendrick later told the Recording Academy. “I saw all the things that I wasn’t taught. Probably one of the hardest things to do is put [together] a concept on how beautiful a place can be, and tell a person this while they’re still in the ghettos of Compton. I wanted to put that experience in the music.” Throughout the album, one can hear subtle nods to both the beauty and conflict seen throughout South Africa. On “Complexion (A Zulu Love),” Kendrick wanted to celebrate the various shades of black women. In the States, some black people were trained to value lighter skin over darker skin, but in South Africa, he saw different shades of people all united by language.
Then on “Mortal Man,” Butterfly’s tremendous closing track, Kendrick—over a jazz-inflected blend of mid-tempo drums and muffled orchestration—ponders his legacy in relation to Mandela’s, wondering if he’ll be remembered as a hero or cast as a villain. Here, Kendrick raps: “How many leaders you said you needed then left ’em for dead? / Is it Moses, is it Huey Newton or Detroit Red?” Mandela himself had seen the euphoria of his release and presidential run dissipate by the mid-1990s. While he brought equal voting rights to South Africa (a huge political shift for the country), life didn’t change dramatically for black citizens after that. Some chastised him for being too nice to the same white people who, historically, had made life insufferable for blac
k people there. He was charming and deeply charismatic, but also economically conservative. “Mandela, and the things that he stood for, aren’t necessarily lauded by young South Africans,” Professor Barnes recalls. “They saw the compromises that he made have not led enough people to feel like their lives have improved.”
“Mortal Man” delves into the kind of survivor’s guilt that Kendrick experienced at the time. On one end, he was beginning to realize his worth, but he couldn’t help but question the authenticity of the love being received. Perhaps he hadn’t done enough work to warrant this widespread adoration. Kendrick did everything with Compton in mind, and toward the end of the track, he concludes his album-long poem by making direct ties between L.A. gang culture and systemic racism in South Africa: “While my loved ones [were] fighting a continuous war back in the city, I was entering a new one, a war that was based on Apartheid and discrimination. Made me want to go back to the city and tell the homies what I learned.” For him, the fight between red and blue was no longer important; black was the most essential color.
He made that message explicitly clear on “The Blacker the Berry,” an aggressive album cut near Butterfly’s end. The South African dissension he referenced, between Zulu and Xhosa tribes, reminded him of “Compton Crip gangs that live next door / Beefin’ with Pirus, only death settle the score.” While these young men killed each other over property they didn’t own, there was a common enemy on the horizon that was perceived to be an even bigger threat than it had been in years past. South African citizens had been known to take bold steps toward their collective freedom; he thought it was time for black men in Compton to do the same.
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