In the music video for the 1991 3rd Bass single Pop Goes the Weasel, MC Serch and Pete Nice are beating an actor playing Vanilla Ice with baseball bats. The actor, with large blond hair and Vanilla Ice’s signature American Flag track jacket, collapsed on the ground moments earlier. Serch and Pete Nice become more aggressive, swinging the bats down with a type of fervour only reserved for the movies. The song Pop Goes the Weasel is a song aimed at the rapid commercial shift happening in rap. The first wave of rap’s commodification was starting at the dawn of the 90s, when aspects of it were becoming less feared and easier for white people to digest, in part because of prepackaged megastars like MC Hammer and, of course, Vanilla Ice. 3rd Bass, a celebrated underground group from Queens, seemed to be fed up with the rapidly changing landscape. And so, the actor playing Vanilla Ice is curled on the ground and we are to believe he is being beaten within an inch of his life.

There is no actor in the video playing MC Hammer. He is not also on the ground being beaten with bats, though he is as much a part of this song’s narrative as Vanilla Ice is: both manufactured, with somewhat fabricated histories, created to push into the mainstream and spread their shadows over everything they could so that white mothers in the suburbs might think of them as “fun, wholesome rap music”, and feel more justified wagging their fingers at the other stars of the genre. The fictional attack that 3rd Bass is playing out in the music video, when looked at through this lens, feels like a type of retaliation.

The joke is that MC Serch and Pete Nice are also white. White rappers taking a bat to a white rapper at a time when the need to separate their whiteness from his was urgent. White rappers fighting to save the world from other white rappers in the name of real hip-hop. The other joke, if you look closely enough, is that the only black member of 3rd Bass was the DJ. His face wasn’t on the cover of the group’s debut album. In the second album cover he is there, in the back.

They Can’t Kill Us Until They Kill Us by Hanif Aburraquib. Photograph: Melville House UK

The funny thing about Eminem is that me and my crew fucked with him because he talked that reckless shit like the white boys we’d known from a few blocks over who would scream at their mothers. One of them, Adam, punched his daddy one day, right there on the front lawn of his house. And his daddy didn’t even do anything except cover his face and shake his head and tell Adam that he was sorry for not letting him use the car. On the eastside where me and my boys were from, if you raised your hand to your father, you wouldn’t be raising it to anything else for at least a few weeks. There is a level of danger that proximity to whiteness makes thrilling, when taken in from afar. Knowing that you could never survive it, or even attempt it in your own life. Eminem was rapping directly into that proximity. For the black kids in the hood, he gained a type of credibility for the ruthlessness and carelessness with which he regarded human life, particularly his own. We understood nihilism, and a desire for exit. We understood anger, angst, bitterness, and the rage that fuelled it. What we didn’t understand was a way to express what we understood and walk away unscathed. Eminem’s fantasies often involved the blood of people who were living, and it must be funny to be on the other side of a fantasy about death.

Expressive and detailed anger is a luxury. Eminem found a way, despite all of his aggression, to turn most of his rage toward pop stars. Christina Aguilera, ’NSync, Britney Spears, Mariah Carey. In his videos, he would mock them while wearing plain white T-shirts to complement his blond hair, sometimes patted down with gel. It was another example of trying to swallow what you might not want to be associated with. Eminem looked, some days, like he could be right there in a boyband: white and welcoming, his most rugged edges only existing when he began speaking or rapping. Eminem’s biggest and best gimmick was about hiding his relentless desire to be separate from the pop establishment while still playing into the hands of it.

Dangerous games … Eminem performing at the 2001 Brit awards. Photograph: POOL/REUTERS

The genre was ready for a white rapper again, after the mid-90s didn’t provide much in the way of white rappers that could be taken seriously in the mainstream. In the underground, absolutely. El-P and Atmosphere were starting exciting careers, but didn’t have any intention to break into the mainstream. Rap fans, a growing portion of them white, seemed to be eager for someone in the mainstream who looked like them. The white kids at my public school in the late 90s would complain about The Source magazine, how it had black rappers on the cover every month. When can I see someone on a magazine that looks like me? they would ask. Whenever I tell that part of the story, people can’t stop laughing. Eminem came with controversy, cosigns, and actual ability. His face was enough to get him into suburban households, and the window he offered into a danger with no repercussions let him into the hood. He was built for superstardom, and his rejection of mostly white pop stars and violent threats against their harmless masses completed the allure. He was a classroom bully. He was living out a type of white fantasy that the more liberal of us would shout down if it happened to be in a suit, in a boardroom, or in the White House. The fantasy of being able to say whatever you want, with no respect for the masses, with the masses rarely wanting you silenced.

Listening to Eminem was like watching my white friend Adam cuss out his parents in broad daylight. Thrilling at first, but then, as I got older, more troubling. I stopped fucking with Adam when he brought a knife to school and threatened a teacher. He got suspended for two days, a week after my boy Kenny from the eastside got expelled for having a small bag of weed in his pocket. I stopped fucking with Eminem when he couldn’t stop making rape jokes in his rhymes as he approached 40 years old. There is a time when all of us have to re-evaluate the distance we actually have from dangerous moments. Eminem has a distance that never runs out. A distance that only grows wider. And there are those who would call him edgy for not realising this, while ignoring those who realise that their proximity to danger is a lot slimmer, and yet they’ve still found a way to stay alive. No one finds this funny.

Machine Gun Kelly performing in Chicago, September 2018. Photograph: Daniel Boczarski/Getty Images

At the Machine Gun Kelly concert in Cleveland, Ohio, he plays a Bone Thugs-N-Harmony song over the loudspeaker. It is a homage to the city’s rap pioneers. Machine Gun Kelly wasn’t born here, but he was made here, in Ohio’s hopeless northeast corner. He is on the verge of a record deal at the time of this concert, Bad Boy Records winning the bidding war for his services. Tonight is a celebration of sorts. Machine Gun Kelly, on sight, is more punk than anything: tonight, his thin white frame is cloaked in a red leather jacket, open to reveal his shirtless chest, covered in tattoos. The black people I know in the area haven’t entirely found themselves invested in the rise of Machine Gun Kelly, feeling that there are black rappers in the city who were more skilled, and I think they’re right. But the buzz of the skinny white kid from the east side of Cleveland had made it down to Columbus, so I wanted to see him for myself. During his set so far, he’s had black people on stage with him, backing him up, accessorising his raps about their neighbourhood and the interior violence of it. He sounds at times, like a tour guide, performing for this largely white crowd in a black neighbourhood. At a show that most of the neighbourhood’s population couldn’t afford tickets to even if they wanted to go.

The Bone Thugs song that he instructs the DJ to play over the loudspeaker is Thug Luv, the 1997 song featuring Tupac, most notorious for its instrumental that is peppered by the sound of a gun cocking and firing on every seventh and eighth count of the beat. The song opens with Tupac, boastful and proud: “It’s time to slay these bitchmade niggas,” he shouts. And, on stage, Machine Gun Kelly steps from behind the mic while his mostly white audience shouts out every word. His black accessories behind him, trying to laugh.

Bubba Sparxxx at the 2002 NME awards. Photograph: Hayley Madden/Redferns

I loved Bubba Sparxxx because he felt genuine. I once watched a rodeo in Bubba’s hometown of LaGrange, Georgia. I ate a funnel cake and let the powder from it coat my dark pants, like everyone next to me. During a break in the performance, a group of rodeo clowns came out and lip synced to Bubba Sparxxx’s hit song Ugly and some people in the crowd square danced. Deliverance is one of the few albums by a white rapper that doesn’t feel like it’s trying to be anything other than what it is. In LaGrange, there are mostly dirt roads. I wore white sneakers that were cloaked in brown within two hours walking around the city. There is the kind of poverty that makes racism easy to bury underneath the performance of shared struggle. In LaGrange, black people and white people sit on porches, or take to fields with shotguns to hunt for pleasure. In the home of an old black man, I saw the heads of three deer hanging on a wall. He would have more, but he ran out of room, he told me.

Deliverance gets lost in the discussion of great albums by white rappers because it came a couple of years after Ugly and Sparxxx’s biggest entry into relevance, but also because it felt so inaccessible to anyone who hadn’t touched their feet to the ground in the south. It’s an album about survival, success, and facing rural poverty. Bubba Sparxxx is, in many ways, LaGrange, Georgia, personified. Eminem felt like Detroit in some ways, yes. But Detroit wasn’t small enough to be singular. LaGrange is the real south, the kind that our grandparents would talk about in the east, in the Midwest. The south where time has frozen, and where stories of making it are currency. Bubba was able to make the south a living, breathing entity that didn’t feel manufactured. In a way that someone like, say, Yelawolf, later failed to do. The second song on Deliverance is Jimmy Mathis, where Bubba raps over a banjo and harmonica: “I’m rappin’ tonight / But as soon as the light hit / I’m all about the green man / To hell with this white shit.” And the joke here is harder to find, but I think it’s that money knows no colour, but our ability to reach it knows every colour, every boundary imaginable.

Deliverance was critically acclaimed, but didn’t even get close to going gold. No one, it seemed, was ready for an album by a white rapper with an overwhelmingly thick southern accent that was drowning in bluegrass instrumentals and stories about mud, shacks, and drinking cheap beer when something better is desired. Bubba disappeared shortly after.

Should it have been Kendrick’s? … Ryan Lewis and Macklemore at the 2014 Grammy awards. Photograph: Steve Granitz/WireImage

My friends say they wish white rappers would write songs facing their own communities instead of pulling a white lens over our own communities. I ask them what we do if the communities intersect. My friends say that more white rappers should write about the spaces black people in the hood don’t know as intimately as the hood. I play Deliverance for them.

No, they say. Not like that.

The thing that should crack me up about Paul Wall is that my homies all thought he was black for a year until we saw his face in a Mike Jones music video. When we finally did, after a year of only listening to songs from the Houston mixtape circuit, we gazed upon his low fade, his white face, his diamond-encrusted teeth. It never occurred to us that he didn’t look the way we looked, and everyone in the room laughed. I didn’t laugh. I couldn’t figure out if the joke was on me or on him.

Some facts about Asher Roth. Asher Roth never sounded as much like Eminem as people would have you believe when we first heard him. Asher Roth pretended to love college to sell records but never finished college in real life. Asher Roth got his song played at house parties but no one listened to his album. Which is probably fine because it got panned by critics for being frat boy navel-gazing. Asher Roth was never in a fraternity, but he looks like he could be. Asher’s first album was the most boring album about partying ever recorded. Sounded like it was written by someone who had never actually spent any time at a party. Maybe that’s true. It’s hard to talk about wild parties stretching long into the night when you’d rather just get high and fall asleep watching old cartoons. I don’t know that from experience.

Asher Roth: I Love College – video

Speaking of getting high, another fact about Asher Roth is that he started rapping like we all knew he could when he grew his hair out and found better weed. In 2009, he was the only white rapper on the cover of XXL magazine’s annual Hip Hop Freshman Class cover, the best class in the cover’s history. Critics loved him at first because he was really excited about being white. But not in the way that white supremacists are excited about being white. He just really liked polo shirts and button-ups underneath sweaters. He looked like a guy you could bring home to parents who live in a house with more than two bathrooms. Jay-Z could’ve signed Asher Roth to Def Jam but instead he signed Pittsburgh Slim. Pittsburgh Slim is also white. A true fact is that it is legally impossible for one rap label to sign two white rappers at the same time without a juke joint in a black neighbourhood being replaced by a Seattle’s Best coffee shop.

Pittsburgh Slim made one shitty album on Def Jam and then got dropped from the label. Just another in the long line of bad decisions made by Jay-Z during his tenure as president of Def Jam Records. Asher Roth signed to Universal Motown and they made him wear sweatshirts with the word “COLLEGE” across them in white letters. They made him show up to radio stations with pre-written freestyles. They made him rap about things that they thought might be relatable to young black people. That’s how the bad album about partying happened. The joke is about how Motown used to spend the 60s selling black artists to white people. Asher Roth was dropped by Universal Motown and didn’t make another studio album until 2014. His hair is long and red now. He looks like he should be playing bass in a metal band. RetroHash was one of 2014’s best albums. It was all about getting high and watching cartoons. No one listened to it. Saw him in 2015 at some festival and a drunk white woman kept yelling at him to play the college song. He never did.

Kendrick Lamar performing in Atlanta, Georgia, September 2014. Photograph: Paras Griffin/Getty Images

The thing is that I don’t think Macklemore feels bad about getting a Grammy. I don’t particularly need Macklemore to feel bad about getting a Grammy, but I especially don’t need him to convince me that he feels bad about having one. On the day after the 2014 Grammy awards, Macklemore started his redemption tour, attempting to show the world how sorry he was for winning the best rap album Grammy for The Heist. An album that was certainly not the best up for the award, but also certainly not the worst. That he beat out the singular Good Kid, M.A.A.D City, released by Kendrick Lamar, was his biggest burden. Macklemore is the Great White Artist of Burdens. I love him most when he isn’t taking himself seriously, but I think he is at his most comfortable when he’s taking himself seriously. When he is, at all times, reflecting on the overwhelming feeling of his whiteness and analysing each corner of guilt that it causes him.

I am sure that there is a place for this, the revelling in guilt for what is afforded to you due to race. It doesn’t speak to me, but I know white people who value Macklemore facing them and challenging them. This makes me feel guilty for just wanting him to make songs where he isn’t lecturing me on the world that I already understand. It is a hard market for a white rapper who seems deeply invested and interested in anti-racist work. A black fanbase will undoubtedly show up for the party and leave for the preaching, and a white fanbase will endure the preaching for as long as they can in order to get to the party. What got lost in Macklemore’s Grammy hand-wringing is that The Heist was, in fact, a good album. It was quirky and odd, but also insightful and honest. It got weighed down a bit by the well-meaning but painfully clumsy marriage equality anthem Same Love being its biggest hit, but it offered enough in the way of fun to offset failures in nuance.

Macklemore and Ryan Lewis: Same Love – video

Macklemore is a more than adequate rapper, his delivery rarely rising above a soothing rasp. He stacks rhymes in a way that would imagine him in the lineage of rappers who truly listened to rap during its 90s heyday. He isn’t a great lyricist, but makes up for it with his ability to build a large world in a small amount of time. He’s also an engaging live performer, spasmodic in all of the best ways, unashamed of making a fool out of himself for the greater good of the audience. The Heist was the fully realised version of all the music before it, the mixtapes that fell short due to unfocused narratives and a lack of fully formed production. On The Heist, the fun served as a complement to the heaviness, which he often times snuck in. Thrift Shop, as a flawed but enjoyable anti-capitalist ode for affordable clothes shopping. White Walls is an anthem for a Pacific Northwest late-night ride-out. During his verse, it’s nearly impossible to not laugh when Macklemore, while describing the Cadillac he desires, raps: “I’m from Seattle / There’s hella Honda Civics / I couldn’t tell you about paint either.”

Same Love was a blessing for Macklemore’s career, but a curse for Macklemore’s worldview. It propelled The Heist to double-platinum status, a gift for an artist who had done the work of rising through Seattle’s underground rap scene. People decided he was important. White people, almost all straight, declared him a beacon of light, an indication of where rap could be going. A “more tolerant and accepting” genre was on the horizon, with Macklemore as its leader. For a few months, the most talked about rapper in the world was white again, and unlike when this had happened in the past, the white rapper met this with conflict. I sometimes think that if Macklemore were either cooler or willing to play cooler, the backlash wouldn’t have been as severe. Black people, who were initially open to embracing him, turned on him heaviest when he took what many of us saw as Kendrick Lamar’s Grammy award. People in queer communities felt justified frustration at him being the face of their narratives. He was, briefly, a white rapper with only an overwhelmingly white audience in love with him. It seemed unheard of, not seen since Vanilla Ice. On the cover of The Source magazine at the end of 2013, he sneered in a brown blazer and a brown suede hat. The cover read: “AMERICAN HUSTLE: 2013’s Man of the Year”. In a corner store, I stared at the cover and remembered, vaguely, the white kids in my high school who dreamed of this day. A white rapper, once again gracing the cover of a rap magazine.

All backlash creates an adjustment, and then new backlash. Sometime in between 2014 and 2016, Macklemore decided that since he had the attention of white people, he was going to start telling them about themselves. It was an exhausting undertaking, an exercise that almost certainly would play out better in a living room than on an album. But 2016’s This Unruly Mess I’ve Made is jarring in its inability to get out of its own way. The first song, Light Tunnels, is another seven-minute apology for winning a Grammy. Growing Up is an awkward open letter to his new child. The album shifts rapidly from confrontational to apologetic, with Macklemore taking aim at his white fans, and then turning to the imagined black fans to apologise for his whiteness. From the standpoint of someone who already understands racism, the album, anchored by the nearly nine-minute White Privilege II is a task. Critics panned it, and it sold over a million copies less than Macklemore’s previous effort.

The white rapper joke starts here … Vanilla Ice and Kristin Minter in the 1991 film Cool as Ice. Photograph: Sportsphoto Ltd./Allstar

You can, in this way, make an argument about Macklemore being the greatest mainstream white rapper of all time, because he was the one most unafraid to sever himself from the comfort of the fame he gained making black art. Being white and profiting off of rap music has never been about skill as much as it is about what can and can’t be sold. If you can both win over white audiences and trick the black ones for long enough, the formula works. The white rapper joke began when Vanilla Ice was corny enough to be hated but not too corny to sell records, and it has evolved to rest at the feet of Macklemore. The ultimate white rapper joke is the white rapper who never wanted to be as famous as he ended up being, but couldn’t help having it happen due to his country’s endless desire for a white face to save everything, even one of the last genres to not be stolen from the people who built it, despite attempts from all angles. What Macklemore didn’t embrace was the thing that Eminem embraced before him: if you are in a system that will propel you to the top off of the backs of black artists who might be better than you are, no one black is going to be interested in your guilt. It has played out in every genre since the inception of genre, or since the first song was pulled by white hands from wherever a black person sang it into the air. No one knows what to make of the guilt. Some rap fans would prefer that Macklemore never rap again. Some would prefer that he rap only directly to white people about whiteness, but that seems to make him less of a rapper and more of a pastor with a thinning audience. Not to mention, his political knowledge, while evolving, isn’t such that he can lead a movement.

But the joke is this: every white rapper is the whole of the white rappers that came before them, because when there are so few of you, it becomes easy to avoid falling into the same patterns. Macklemore did what I would have hoped he would have done, even if he did it painfully and with a tone of self-congratulation. What no other white rapper was able to do before him. He stopped just apologising for what he imagined as undeserved fame and instead weaponised it, losing fans in the process. The major function of privilege is that it allows us who hold it in masses to sacrifice something for the greater good of pulling up someone else. Macklemore, whether intentionally or not, decided to use his privilege to cannibalise whiteness, tearing at his own mythology in the process. When I saw him last year at a festival, he performed White Privilege II to a captivated white audience. Halfway through the song, he left the stage entirely empty, walking off and making room for two black poets and a black drummer to read poems about police violence and gentrification. It was a stunning image, an artist holding the mouth of his audience open and forcing the slick red spoonful of medicine down their throats.

I don’t think this is heroic as much as I think it is necessary. But anyway, this was never about heroes. My heroes are the backpack MCs who made a lane for white rappers to hone their skills enough to get record deals, leaving them behind in the process. But you’ve been waiting for the punchline, and here it is: in a country that wanted more than anything for him to be the man to lead rap into something they imagined to be better, Macklemore chose to instead make himself a man without a country.

And isn’t that funny.

• They Can’t Kill Us Until They Kill Us by Hanif Abdurraqib is available now from Melville House UK