'It Was Freaking Bananas!': Rap Luminaries On The Defining Moments From 50 Years Of Hip-hop

I must have been only five or six when I attended my first block party in the mid 1970s. I was riding on my big wheel bike and from behind the handlebars I looked in awe at these turntables that were out the front of my high-rise, building number nine of the Pink Houses projects in Brooklyn. The power leads went all the way up through a window to an apartment on the fifth floor. The turntables belonged to this crew called the Together Brothers. It was like one big free party – all the adults were dancing and partying, smiling, drinking alcohol.

Hip-hop was this new sound, so it wasn't being played in clubs yet. The block was our club, and the whole hood would come out to dance. Later on, the block parties and the jams in the five boroughs turned into shootouts. You had people messing up the vibe! But in the beginning, it was all about community spirit.

I didn't start DJing properly until I joined Salt-N-Pepa in 1985. One day I was in maths class, the next I was spinning on our first world tour. I remember the men used to say I couldn't spin properly and was only there because of my looks, but I didn't need my looks to get the party rocking! Salt-N-Pepa wasn't just about having fun, but empowering women too, and I guess I was one of the first visible female DJs in the mainstream. Those block parties were the start of something special.

DJ Muggs of Cypress Hill on the arrival of the E-mu Sp-1200 From left to right: DJ Muggs, Eric Bobo and B-Real of Cypress Hill. Photograph: Dave Tonge/Getty Images

Once Marley Marl started sampling, it really flipped the whole rap game on its head and created this new artform. Even if I only had $20 to my name, I would go to the 99 cent van and buy 20 records to sample, based on how cool the artwork looked. That's the beautiful thing about sampling: the sense of discovery. It made us appreciate hip-hop's roots in blues, jazz, soul, and funk.

E-mu SP-1200, sample-based drum machine.

Everyone was sampling James Brown, so the challenge was digging deep in the crates so you could find something new. Back then you weren't allowed to sound like anyone else. If Cypress Hill sounded the same as NWA we would have been booed off the stage! You couldn't dress like anyone else or use their slang either.

It was the arrival of the SP-1200 in 1987 that changed things. You might have a jazz song that's 14 minutes long and there's a one-second chord change that sounds really special. With the SP-1200 you could extend and loop that one moment until it becomes this whole other musical world. Me, Alchemist and Madlib might all hear the same song, but be inspired by different sections and each use different samples. That's the beauty of the sample. When you found the perfect sample and flipped it into something new, it was like discovering a piece of gold! For rap producers it remains the best feeling in the world.

DJ Shadow on the power of the first Def Jam Tours

The Def Jam Tour was hitting Oakland, which was about a 90-minute drive away. I told my parents I would do all the household chores for two months if they let me go. It was 1988 and I was only 14. It was also a school night, but I really laid it on thick to the point where they had no choice but to say yes.

I had become obsessed with hip-hop a few years prior when I heard The Message by Grandmaster Flash and the Furious Five on the radio; it sounded like the truth in musical form. I recorded it on cassette. What I really loved was the mysteriousness of the DJs. On Run DMC's album artwork you never saw Jam Master Jay, but it made him feel like this magician or director who was pulling the strings from the shadows. That's why I called myself DJ Shadow.

We never made it to the show, as my mentor Oras Washington's car kept breaking down. We did make it to the afterparty, though, which was held at a Holiday Inn next to a freeway. There I met EPMD and Chuck D and Flava Flav, who previewed Public Enemy's Rebel Without a Pause to everybody on his boombox. A fight broke out, so Oras took me back. The whole ride home I was silent: all I could think about was making music for a living. That day confirmed it. I'm sure everyone who went to those Def Jam shows in the 80s left feeling inspired.

Big Boi of OutKast on the revolution of NWA's Fuck tha Police NWA pictured with rappers The D.O.C. And Laylaw in 1989. Photograph: Raymond Boyd/Getty Images

When it came to the police in Atlanta, there was a lot of corruption. I was in high school when the Rodney King beating happened. It sparked the riots in LA, but there were also protests out here in Atlanta. We caught the train downtown to see what all the hoopla was about. We wanted to see the uproar and ended up getting caught up in the rowdiness a little.

Hearing Fuck tha Police was like the ultimate moment of rebellion. Rap music was the voice of the youth, so hearing NWA lash out in that way really resonated with me. Knowing you could have that kind of voice, and say "fuck tha police" out loud, was something felt across the globe.

That song taught me that OutKast had a responsibility to say something about social issues whenever we got on the microphone. It wasn't just about dancing or playing around. You really had to put some substance into your music.

Pete Rock on the body positivity of Heavy D

My first cousin Heavy D and I made cookies in the kitchen together and would borrow each other's clothes as children, so when he was suddenly on songs with Michael Jackson [Jam] and Janet Jackson [Alright] it was freaking bananas! We owe everything to DJ Kool Herc for starting hip-hop and we're all cut from his cloth, but without Heavy D blowing up, so many rappers wouldn't exist today.

Heavy D and The Boyz. Photograph: Al Pereira/Getty Images

He convinced Uptown to hire Sean "Diddy" Combs, inspired the Ruff Ryders and he was the one who made me believe I had skills as a rap producer. He also gave people like Biggie, Fat Joe, and Big Pun their confidence. Heavy D was the first rapper to show the bigger guys how to love themselves. Rather than be teased or cracked on, he showed us how to turn the insults around and that you could still be a sex symbol even if you were overweight.

Heavy D and the Boys were the first rappers that your mom liked, too, which helped to cement hip-hop in the mainstream, globally. I get so angry when they don't mention his name; you can't celebrate hip-hop without mentioning Heavy D.

Kool Keith on hip-hop going international

I remember me and Ced-Gee [from Ultramagnetic MCs] toured France and all the people were eating 30-year-old cheese that smelled like feet. It was nuts! We also got a chance to go to a nudist beach over there, and there were 90-year-old women and men walking around naked with afros for pubic hair.

I also played a show up in Brixton, where the Jamaicans were going crazy and there were red phone boxes just like in the movies. We went out of the city and ended up getting lost in the woods; this British farmer threatened us with a shotgun, because we accidentally walked through his back yard!

Kool Keith in Chicago, 1999. Photograph: Paul Natkin/WireImage

I was lucky to tour across Australia and even performed in the Cayman Islands. No matter what city I would go to, I would find the local [instrument] store and practise playing funk on the keyboards and guitars. I was exposed to the different food and delicacies but I guess I was too Bronxed out and didn't understand it, because I always ended up going to McDonald's or KFC. But going to all these places showed me how international hip-hop was and how it transcended cultures. Hip-hop allowed me to travel. Not bad for a kid from the Bronx, right?

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Young Jeezy on the death of Tupac Shakur

I first heard Tupac when I was locked up in prison. When I played So Many Tears it felt like he understood me. It was more like a great sermon than a rap. None of my uncles were teaching me about politics or why we were suppressed as Black people, but Pac was preaching and it gave me a moral compass.

When Southern trap took off, we were trying to give the people a class on the blood, sweat, and tears that the hustlers in the street go through. We let the outsiders walk in our Air Force Ones for a day. If you are in the wilderness and trapped there, you do what you have to do to survive. Even though making money through dealing drugs might be negative to some, for us it wasn't about being evil or harming others; it was purely about survival.

Tupac was one of the first to understand our pain. He humanised the people in the trap. The Black men who play this role always end up dying young. They get taken out from their own people because they become too powerful. When Pac got murdered [in a drive-by shooting in 1996], the culture lost its heart.

Rapsody on Lauryn Hill winning the Grammy for album of the year

I was a teenager falling in love, so when I heard the Fugees' Killing Me Softly for the first time, I was obsessed. In the music video they are in the theatre; no one ever looked cooler eating popcorn than Lauryn Hill! I connected with Lauryn because of the truth and honesty she displayed in her music.

Lauryn Hill during the 41st Grammy awards. Photograph: Steve Granitz/WireImage

When she won the Grammy for album of the year for The Miseducation of Lauryn Hill, it was a huge moment. It was special because of what she represented. Lauryn had this fearlessness and made us question the things around us. She didn't get caught up in the fantasy or illusion of American capitalism. She was always asking: what is the truth?

Sometimes it can be easy to get caught up in the program, but Lauryn was our Neo in The Matrix and our compass. Today there aren't enough Lauryn Hills in the mainstream. But Lauryn showed us how to love ourselves and that there was a space for all versions of Black women.

Mykki Blanco on how Lil Kim's No Matter What They Say video spoke to LGBTQ youth

I was only 12 or 13 when Lil Kim's No Matter What They Say music video came out. I was living in a tiny house in the countryside in North Carolina, so to see Kim looking so glamorous in this ornate, Louis XVI-style dressing room really blew my mind. You had the hair extensions that made her look like Rapunzel and the swinging silver dress. As a queer child, to me Kim's sense of exaggeration as a performance artist felt like a real affirmation. She was the epitome of glamour.

There's this moment where she is wearing these cut-up, bleached jeans. Let me tell you: the week the music video came out, every Black girl at every high school in America went out and got a pair. My mom even let me bleach and cut up a pair of jeans. You had Kim alongside Mary J Blige, Carmen Electra, and Missy Elliott in the video: it was this absolute proclamation of sisterhood and self.

Kim's lyrics about "bitches making faces like Ace Ventura" became my whole attitude. If you were a queer kid who was sheltered and not exposed to much, a music video like that was foundational. When Kim said "I'm just trying to be me", it made us love ourselves.

Flo Milli on why Nicki Minaj's Monster verse empowered her generation

Nicki Minaj's verse on Kanye West and Jay-Z's Monster is one of the things I remember most vividly from my childhood. Me and my sister would always rap it together in the house. "Pink wig, thick ass, give 'em whiplash / I think big, get cash, make 'em blink fast" were my favourite lyrics because of the stamina [of how Nicki rapped them]. It was so crazy. The energy was unmatched, and you had no choice but to be drawn in.

Nicki Minaj performing with Jay-Z and Kanye West in New York, 2010. Photograph: Kevin Mazur/WireImage

With that Monster verse it was like yes, you can come into hip-hop as a female and still carry that same alpha energy. Nicki was so multifaceted. Whether you were the Black Barbie or the weird kid, she had something for every young girl to tap into.

When I was 10 and told people I wanted to be a rapper when I grew up, it wasn't really accepted. But in 2023 I feel really strong being a woman in hip-hop. It has been a long road, but we're no longer dismissed like we used to be. Nicki let young girls know they could still dominate a rap game that was male-dominated.

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When hip-hop first hit London in the 1980s, it was infectious. In Battersea, we first got it in the form of b-boying, and it felt like everybody belonged to a dance crew. We would all gather at Covent Garden to play music and everyone was popping, locking, and breakdancing. When the Sugarhill Gang or Grandmaster Flash and the Furious Five performed on Top of the Pops for the first time, it made the British Black youth feel seen. The Thatcher years were rough, so hip-hop became this beacon of light for the poor, where everyone was on an even plane.

When I moved to New York, I wanted to elevate young mothers with my raps but nobody wanted a woman rapping in a British accent. So, to see 2-step garage evolve into grime and then to see people like Drake start emulating British flows and lingo [in the 2010s] was powerful. There was no more ridicule and it was a turning point.

Over in New York, where I live today, people will proudly tell you they listen to Skepta or Giggs. The Americans want to sound like the British now, and London and New York have this bridge that links them together because of artists like Pop Smoke. Everything has gone full circle.

The caption for the Cypress Hill image in this article was amended on 25 August 2023. It shows, from left to right, DJ Muggs, Eric Bobo and B-Real; not DJ Muggs, B-Real and Sen Dog as an earlier version said.

Dave Portnoy Bought Barstool Back. Can Erika Ayers Badan Keep His Pirate Ship On Course?

Erika Ayers Badan kicked off her heels and sank into the quiet of her Connecticut home. It is February in 2023, thick into the spring sprint for Barstool Sports, the company she's run for seven years. There was the Super Bowl, March Madness. And then there was the deal with Penn Entertainment, a casino and racetrack company, to fully acquire Barstool, after buying a third of the business years earlier, with plans to take on the whole thing. She knew it was coming, but these last few weeks were filled with minutiae. She paid visits to all of the cable business channels to field questions about what this would mean for the company, which has revolutionized the way media companies build community and make money even while stepping in shit by being unapologetically themselves. (Barstool being itself meant being relentlessly chaotic and behaviorally tricky.) She led town halls with hundreds of employees. She recorded episodes 260 and 261 of her podcast, Token CEO (on Barstool, of course). She bought David Portnoy a bottle of wine from 2003—the year he founded Barstool as a free hometown subway newspaper in Boston, backed by $25,000 from his parents, for other Red Sox bros commuting. ("The people at Barstool Sports are a bunch of average Joes, who, like most guys, love sports, gambling, golfing," he wrote in his first issue, "and chasing short skirts.")

Ayers Badan, who recently remarried and changed her name (dropping the Nardini she'd been known by), is an advertising vet from her Microsoft and AOL days, and was already one of the highest ranking women in sports media. She won the Barstool gig over 74 male candidates. Back then, the staff worked out of an old dentist's office in Milton, Massachusetts, with a squirrel living in the radiators and eating their internet cables, trash that no one would take out piling up in the corner. The only way people communicated was through text message. There was one bathroom and no payroll. Portnoy paid his staff with personal checks, which sometimes competed with his gambling losses.

On this February day in 2023, the Penn deal closed for $550 million, netting Portnoy around $100 million, according to Portnoy on Logan Paul's podcast. "What are you doing to celebrate?" she texted Portnoy and Barstool's first employee, Paul Gulczynski (known as Gaz), once she finally sat down that night. Nothing, they responded. What was she doing to celebrate, they asked. Nothing, she replied. There were things to feel proud of and exhausted by, sure. And, if she was being honest, a little grief too. "It felt like the end of an era, this challenger brand that came out of nowhere," she said at the time, "that never should have made it, and yet here we were, true to ourselves, making it."

Barely six months later, Ayers Badan and Portnoy were seated across from each other for dinner at Zero Bond, the members-only club in NoHo with a no-photo policy, and, as such, a mecca for celebrities. It was a celebration of sorts, but the tone was different, and so was the purpose. It was the dog days of August in New York, a few hours after the news broke that Portnoy had bought back Barstool from Penn for $1. The deal, which Ayers Badan said came together over two weeks, was the result of a separate $2 billion alliance between Penn and ESPN. Penn had been eager to tap into the $220 billion Americans have bet since it was legalized five years ago, and hoped that Barstool was its ticket to competing with giants like FanDuel and DraftKings. Barstool is big, but ESPN is bigger, a scaled behemoth that had yet to fully dive into that market itself. ESPN is also part of Disney, whose family-friendliness is also business-friendly in a highly regulated industry. Barstool, by contrast, represents approximately 2% of the gambling market share. And, largely, by the nature of who they are and what they do, the lion's share of the headaches.

"We underestimated how punitive the regulatory environment was and how stringent it was going to be," Ayers Badan told me the morning after the deal was announced. "Really, at the core, what Barstool is about—entertainment, satire, comedy, opportunistically capturing and creating viral conversations on the internet—that is so antithetical to what a highly regulated industry wants, or what the stock market likes, that [Penn] just became a place where this just was not working."

To its credit, she added, Penn embraced Barstool for what it was. They never asked for change. But they hit hurdles almost immediately. For example, one of Barstool's biggest personalities, Dan "Big Cat" Katz, who hosts "Pardon My Take," launched "Can't Lose Parlay," which, to his audience, was a bit of a joke, because, as Ayers Badan pointed out, he is "arguably one of the worst bettors of all time and he always loses the parlay." The gambit landed them in a regulatory hearing in front of the Massachusetts gaming commission, who claimed that the name was deceiving customers by using the language "can't lose," even though it was very likely that they would. Additionally, as long as they were talking about football in the context of betting, state regulations wouldn't allow Barstool to do shows on any college campus, which is a demographic linchpin for Barstool's growth strategy. And then there was the issue with how Penn's stock dipped with each article, including Business Insider, that detailed allegations of sexual misconduct and gambling debts about Portnoy. On the news of the ESPN deal, Penn's stock surged more than 20% after hours.

"All of this put Barstool in a tough spot," Ayers Badan told me. "It put Penn in a tough spot. It also put me in a tough spot because I'm trying to grow a robust and rowdy and meandering brand where I don't know what we're going to be talking about next week, next month, next year, but I do know that, to grow Barstool and to have Barstool be relevant, and vibrant, and meaningful, it has to be able to explore comedy, and entertainment, and lifestyle and things that, honestly, just are really difficult in a highly regulated, highly punitive environment."

Everyone has their "MOUTHS HANGING OPEN over what Dave Portnoy's doing," says Ayers Badan, "and I'm over here BUILDING A BUSINESS."

And so Penn sold its ownership back to Barstool in exchange for 50% of Portnoy's proceeds on any future sale of the media brand, and a noncompete in the gambling space, which industry experts said would likely last just through the coming football season, and other restrictive covenants. Portnoy, for his part, said that he won't sell the company again. "I have no intentions of ever really selling Barstool," he told me the morning after the announcement. "I think we're in a very good situation and unless we're total idiots, we shouldn't have to worry about the bottom line anytime soon."

Well, Ayers Badan might worry about it, because that's her job, and one she has done for seven years with remarkable skill and success, including even the August U-turn. (And she says she has no plans to go anywhere else.) But if you asked most people who is in charge of Barstool, they would say Portnoy. He goes by El Presidente—or "El Pres"—for starters. And he is a god to cancel-culture-bemoaning, pizza-loving, red-blooded Robinhood traders. He's Donald Trump without the politics (so, really, Donald Trump) for the Everyman in the internet age and has described Barstool Sports as "a localized Maxim" for "young middle-class white guys who like sports."

But Barstool ballooned well past his wildest intentions. By the numbers, Barstool has more than 100 podcasts, YouTube shows, and social media series; 95 personalities; 65 advertisers; 17 content verticals; countless merchandise sold; and more than 230 million followers across social media. Its 1.2 million annual pieces of content and 5 billion monthly video views reach a third of 18-to-34-year-olds. Where it stands to really level up, as far as Penn saw it: online gaming, a $63.53 billion industry, among competitors like DraftKings, now a publicly traded company worth around $14.11 billion.

"Everyone is all focused with their mouths hanging open over what Dave Portnoy's doing," Ayers Badan had told me earlier this spring in the company's midtown Manhattan offices, "and I'm over here building a business."

Ayers Badan grew up in Gilford, New Hampshire, the daughter of a vocational school teacher and a superintendent who saw no need for television in the house. On the first of each month, she would call the cable company to try to set up an account in her parents' name. "I'd be like, 'Hi, my husband made me cancel my TV, and I'd like to bring it back this month,' " she told me. "My mom would figure it out, and then I'd just do the whole thing over again."

She describes her young self as "supercompetitive": Each day, she counted the number of steps between home and school; the next day, she would try to make it in fewer. She cut her teeth in a handful of big marketing jobs at Fidelity, Microsoft, and Yahoo, among others, but hit a ceiling. When she heard that Barstool was hiring a CEO, she pounced. She had been a massive fan for years, as a New England girl who rocked a few Barstool T-shirts, which she pursued despite the fact that she had to buy them on "this horrendously janky website where your credit card was 100 percent going to get stolen." She begged a Barstool consultant she knew for a meeting with Portnoy, which he believed was a spontaneous run-in. He's already met with dozens of what she called "white guys in vests and blue button-ups with an MBA." She turned up to the meeting in an Isabel Marant dress with cutouts and kitten heels.

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