In 1985, many Hip-Hop artists were just starting to get major-label record deals. Even the most ardent supporters of the culture thought there was a finite shelf life on the culture. Many even predicted a doomsday scenario in which Hip-Hop would go the way of disco. As a result, artists were posturing to stay both relevant and paid. Unfortunately, Hip-Hop’s growth came at the expense of Roxanne Shanté’s wildest dreams.

In 1980, Tom Silverman (who would go on to start Tommy Boy Records) and three other partners founded an industry networking event called the New Music Seminar. In a short amount of time, the festivities became fertile ground for MCs and DJs looking to prove who was best on either the mic or the 1’s and 2’s. Music journalist Robert Christgau wrote of the inaugural event, “A mildly Bohemian one-day affair in a friendly recording studio.”

Five years later, Roxanne Shanté had her eyes dead set on winning the WWF-style championship belt that came with winning the “Battle for World Supremacy” at the Marriott Marquis. It wouldn’t be easy, but Shanté knew she had the stripes to do it.

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As the youngest and only female MC participating, Shanté immediately got the sense that the deck was stacked against her. Unlike a traditional seeding structure — like a basketball tournament, where you beat an opponent and move on — it was apparent that Shanté would basically have to beat everyone in the field.

“Shanté was knocking off all the name-brand guys,” says inaugural battle champion Busy Bee. “I didn’t even have a chance to.”

The seeding system certainly didn’t bother Shanté. She was a prolific freestyle artist. Most of her opponents had to write their rhymes. As a result, she always felt she had the edge in a multi-round battle when the heat got turned up. 

“It was Roxanne against everybody that day,” she says. “And I said, ‘Okay, this is no problem.’”

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In her mind, she’d take home the prize, win it in front of MCs she respected, and then get to take her sisters out for a steak dinner at nearby Beefsteak Charlie’s in Manhattan.

“I laugh at it now because I think the steaks were like $7.99, but it was a big deal back then,” Shanté says.

Shanté likens her threat-assessment ability to Jason Bourne’s style of heroism in an action flick. Whereas the fictional character might be looking for signs of trouble, Shanté was explicitly trying to expose what a rival MC hoped would remain hidden.

“I will look and I will find something,” she says.

“I don’t usually use it to find the flaw in order to humiliate anybody — because that’s not my nature. But should there be a situation, I know where there is a flaw. I could talk about their clothes, I could talk about who was with them, I could talk about them stopping to get water, I could talk about it if they choke, I could talk about if they stuttered.”

There were no easy victories to be had during the individual five-minute battles, where MCs traded barbs in four-bar increments. One of her first battles was against Tommy Boy signee Frukwan of Stetsasonic (who later became a member of Gravediggaz alongside the RZA). Shanté used tractional insults to set traps like a seasoned pugilist — latching onto his dark skin, yellow teeth, and ugly clothes. The crowd was enamored with her ability to consistently go in for the kill. As Fruitkwan began to sense he was losing, he unleashed a sexually laced innuendo. Shanté merely laughed it off by indicating that his “member” was too small to even consider.

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Shanté dispatched one rapper after the other until her voice was hoarse. She had consistently gotten no score lower than a nine from celebrity judges DJ Red Alert, Grandmaster Caz, Marley Marl, Kool Moe Dee, and Kurtis Blow. When the dust settled, she had reached the championship round to face Busy Bee — an MC whom she considered the “ultimate party rocker.”

“I got this,” she thought. “I’m going to be fine with this one. So we really going to Beefsteak Charlie’s now — like yeah, just get it, get the menu, we on.”

Like with sports, a certain amount of gamesmanship goes into getting the mental edge during a rap battle. Despite being adversaries in the moment, Busy Bee encouraged her to go as hard as possible — even if that meant ignoring a newly installed rule that cursing was no longer allowed.

“I said, ‘You can do what you want,’” Busy Bee recalls. “She said, ‘We can curse and everything!?’ I said, ‘Yeah, you could do what you want to do.’ But I knew it in the rules that she actually wasn’t supposed to curse.”

The back-and-forth was a contrast in styles. Busy Bee had a singsong approach more indicative of the Master of Ceremonies in the ’70s. His most effective lines were more about his own personal greatness than Shanté’s lack of skill. On the other hand, the 15-year-old Queensbridge native took every opportunity to remind Busy Bee how ugly, dumb, and mismatched he truly was.

The celebrity judges were instructed to score the battle based on creativity, uniqueness, and skill. When it was time to decide a winner, they would each hold up a number like in the dunk contest. Shanté figured that if there was any bias against her, it would come from DJ Red Alert, because he handled the 1’s and 2’s for one of her rivals, Sparky D.

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“But Red Alert gave me an eight because he understood Hip-Hop,” Shanté says.

“He said, ‘Nah, she’s good, she’s good. She has it, that’s it. She’s going to be the best in the world.’ Now I’m looking at all of these MCs, entertainers — even R&B artists — and I’m saying like, ‘Wow, I’m going to leave out of here the best in the world at something.’”

Shanté was ahead on all the cards. The only way she could lose was if someone intentionally sabotaged her. As she would later learn, that person was Kurtis Blow. He asked what number he needed to give her so that she would lose.

Four.

So that’s what Kurtis Blow gave her.

“She only lost by two points,” Busy Bee says.

In Shanté’s mind, this was the day that she officially fell out of love with Hip-Hop. She had always reconciled the fact that in order to be the best she needed to beat the best. This battle had illustrated something different.

MC Chill was in attendance that day. He later confirmed that the fix was in. Blow gave it to Busy Bee because, “He’s from the old school.” Shanté believed that this factor — coupled with her own age and gender — made Blow bet that the future of Hip-Hop culture was stronger if someone other than a teenage girl carried the torch.

While Busy Bee isn’t willing to officially state that the fix was in, he does understand that there was an underlying point to Blow’s actions.

“These were men, and we were becoming men together,” Busy Bee says. “But she held her own, man. And still today, she’s the queen of what she did, and how she did it. I give her those props.”

Roxanne Shanté isn’t bitter about the robbery. However, she sees her perceived failure as one of the major factors in Hip-Hop’s subsequent growth. In her mind, she understood that Hip-Hop needed to be a boys’ club before it could be all-inclusive and blossom into a multibillion-dollar business. But she still thinks there’s a lot of room for improvement when it comes to getting respect, regardless of your age or gender. She champions what she calls “She MCs” on her social media. However, Shanté will never be one to shy away from a battle.

“In order to show your children that you love them, you must also discipline them,” she says. “So every now and then I can do that. That brings a balance. You can’t have one and not the other. I can’t take the battle MC out completely. I can grow wiser, but it’ll always be there.”

* Banner Image: Roxanne Shante / Photo by David Corio/Redferns