How Chicago’s ‘drill’ music scene set a template for Toronto’s underground rap stars — and their feuds

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As a newly minted sociologist searching for the cause and consequences of violence, Forrest Stuart turned to music.

The California native had DJed internationally before finishing his PhD and, with that background, he helped create an after-school program for arts and audio production to help South Side Chicago teens make music and process trauma. It was in that program, in a gang-saturated part of one of America’s most violent cities, that Stuart met the Corner Boys and first learned of “drill” music — a rap genre characterized by dark lyrics that celebrate drug dealing and violence.

Stuart followed the Corner Boys for two years, from 2014 to 2016, which he chronicled in his highly readable 2020 book, “Ballad of the Bullet: Gangs, Drill Music and the Power of Online Infamy.” Amid extreme poverty, limited job options, looming police surveillance, and near-constant threat of violence, a couple dozen young men created and uploaded their homemade, hyperviolent and gun-filled music videos to YouTube “with dreams of drawing enough clicks, views and likes to punch their tickets out of poverty,” Stuart described in one online post.

“Unfortunately, many of the online personas they build leave them behind bars, seriously injured or dead.”

Do-it-yourself rap production and digital promotion are booming in cities around the globe, including in some of Toronto’s most marginalized neighbourhoods where jobs and opportunity are scarce, and gun violence is common. Also booming here: the same cycles of online mythmaking, provocation and retaliatory violence that Stuart describes seeing first-hand in Chicago’s drill scene.

In recent years, several popular underground Toronto rappers have been killed amid feuds that have played out online. Several others have been charged with serious violent offences; earlier this year, one of Toronto’s most talked-about rappers was arrested on a charge of accessory after the fact to murder.

“I’m a rap star,” Hassan Ali — who performs as Top5 — snickered during a recent exchange in a livestream on Instagram, where he has more than 130,000 followers.

Ali is both admired and vilified for the content of his videos, which are replete with insults and threats to rivals, and for provocative Instagram live disputes where no boast is too big. Last year, he was charged with mischief for stopping traffic on Highway 401 to shoot a music video.

And the attention-seeking seems to be working.

“We see the antics online but listen, that’s smart marketing bro,” DollarBoiEnt, a New York-based YouTuber who has started critiquing Toronto rap videos, said as he watched Top5’s latest music video.

“Why you think his numbers are going up? Why do you think he got the views? It’s not just about the music in this industry, bro, it’s about the internet clout, it’s about the marketing; it’s about, you know, you got to play the game.”

In “Ballad of the Bullet,” Stuart traces the origins of drill music to a Chicago teen named Keith Cozart who, performing as Chief Keef, became a phenomenon at the start of the last decade. A rapper with a local following at his high school and in his neighbourhood, Chief Keef’s popularity exploded when he started posting music videos shot while under house arrest and living with his grandmother.

His run-ins with the law, online taunting and lyrics celebrating the deaths of rivals became fodder for local music bloggers hungry for sensational content that might increase their own visibility.

Chief Keef’s infamy helped him become a breakout star with a $6 million (U.S.) record deal that, in turn, inspired legions of Chicago teens, Stuart said.

“This is it, bro,” one of the Corner Boys told Stuart as they sat in his parked car watching Chief Keef’s notorious video for the song “I Don’t Like.” First posted in 2011, the video has been seen tens of millions of times on YouTube — “This is the video that started it all,” the Corner Boy said.

Chief Keef’s success is “an American parable bootstrap story that this guy, on the backs of hyperviolent gangster rap on YouTube, is able to jettison himself out of poverty,” Stuart said in a phone interview, speaking to the Star from his home office about 15 kilometres north of Stanford University, where he is a sociology professor and director of the Stanford Ethnography Lab.

In 2021, the template set by rappers like Chief Keef is firmly established.

“Be so sensational that you attract lots of eyeballs and capitalize on the fact that, given the economy, these record labels had to cut their A & R talent budget, so they’re looking for artists who already have a fan base on the internet and they know will sell records and they know will make headlines,” Stuart explained.

If there is one single dominant theme in what works online, it is an appeal to authenticity, which can also create unintended problems, he said — “It’s a claim that ‘every thing I’m talking about I actually do them,’ I have first-hand knowledge doing all this stuff I talk about.”

Not that the claims of violence are necessarily true.

Stuart said he saw first-hand many examples of the Corner Boys exaggerating their claims about their ferocity. “If true, the city would be burning and these guys would be locked up if they even did a tenth of the violence that they claim that they’re doing,” he said.

It also irks him that cops and others can’t understand why young men from poor backgrounds would record themselves admitting to crimes — so-called self-snitching — in their music.

He recalled one of the Corner Boys posting his phone number on Twitter to tell fans he was having a bad day.

“Here’s this guy, broke and broken down, distressed, living in pretty terrible conditions and he’s got a stream of people telling him they love him; women, white and affluent, wanting to have sex with him,” he said.

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“Imagine you’re a 17-year-old who’s been told you’re worthless your entire life and suddenly you found a way to get people say you’re amazing and sending you love letters.”

In Toronto, a similar ecosystem of online fans, bloggers and YouTubers has grown up around the extremes of this city’s underground music scene.

A decade ago, popular and controversial DJ Akademiks, a U.S.-based music and culture commentator, ran YouTube channels keeping up on Chicago’s “drillers” and their associated violence, prompting criticism for his sarcastic delivery and claims he was exploiting a tragic situation.

Last year, he began shining a light on Toronto, hosting live chats with this city’s rappers.

Akademiks, whose real name is Livingston Allen, says that today he has a better understanding of why young men vie for recognition and “likes” in the attention economy. After Ali’s arrest, Akademiks told his audience of 2.4 million YouTube subscribers the young man’s bluster is misunderstood.

“I showed Top5 my house, my cars. He said, ‘Ak, bro, I want to live like you, I don’t want to be here beefing … I am trying to get out of this situation,’” Akademiks said. “It’s unfortunate that rap, at times, you have to be mad-graphic, you’ve got to be beefing just to get out.”

Top5’s many critics — including Toronto police — describe it differently. They contend the 22-year-old also stirs up trouble on the streets. The rapper was allegedly in a car when an innocent man was shot and killed last fall in northwest Toronto. He is applying for bail next week.

The tragic irony is that the bigger the name in the drill world, often the larger the target on your back. Since 2018, two of Toronto’s best-known underground rappers, Jahvante Smart — who performed as Smoke Dawg — and Dimarjio Jenkins (Houdini) were murdered in broad daylight in the downtown core.

And while the internet has democratized music creation and distribution, those reaping the financial rewards aren’t necessarily the artists themselves.

In Chicago, it wasn’t the young “drillers” but other players in the content-creation business who made the real money, such as YouTube channel owners and the social media giants, Stuart said.

They, in turn, profit the most from sensational, algorithmically tuned content.

“The YouTube channel owners don’t just want any video, they want the guys who are the most violent seeming, the guys with the most guns, the guys with the most drugs in their videos, the guys who are making the hardest diss tracks, who are threatening death against other people, who are talking about the worst crimes.”

Stuart also writes about finding links between crime and drill one wouldn’t expect.

“Some of the young men I spent a lot of time with would do robberies, because the money they would get from the robberies they could use to hire someone to shoot their music videos,” said the sociologist.

“Yet again, young people in disadvantaged neighbourhoods are committing crimes just so they can start doing the only available opportunity for them to be told they’re special and feel some kind of status.”

If society wants something different, “we really do have to create new and legal opportunities for them to carve out dignity, feel special, gain status and eventually make a sustainable living.”

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