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How Three College Pals Created Standout Hip-Hop Label Generation Now

How three college buddies who came up in the ’90s Atlanta scene turned decades of experience — and relationships — into the tastemaking label Generation Now.

This story is part of Billboard‘s annual R&B/Hip-Hop Power Players list, which spotlights the executives who continue to push the genres forward.

It’s the late 1990s, and Southern rap music is beginning to bubble up in the mainstream. In New Orleans, Master P’s No Limit Records is gaining steam on the heels of his “Make Em Say Uhhh” and Cash Money Records is thriving on buzz from Juvenile and Lil Wayne. Memphis is entering the fray with the emergence of Three 6 Mafia. And in Atlanta, OutKast is making a bid for hip-hop’s crown, following its seminal album Aquemini. Throughout that city’s historically Black college campuses, students are looking to break into the scene — including three young men who will one day help change the sound of hip-hop.

At Clark Atlanta University, Tyree Simmons studies communication by day; by night, as DJ Drama, he crafts mixtapes with the hottest new tracks. His Clark classmate and friend Don Cannon, who’s studying business management, lives in a dorm full of aspiring rappers, so he starts honing his own DJ skills and begins producing, eventually hooking up with Drama and DJ Sense to form a crew called The Aphilliates. Just a few blocks south, at Morehouse College, Leighton “Lake” Morrison — a political science major who dreamed of being an MC since age 15 — takes a job at a nightclub, where he meets Cannon and, later, Drama.

Now, after 20 years and various jobs in the music industry, the friendship the trio built has not only survived but thrived — and it’s the foundation of their flourishing label, Generation Now. “Through us all growing in the music industry, we just kept in touch,” says Lake, 41, today over a Zoom call with his longtime friends and partners. “It turned into conversations, and conversations turned into a business.”

Generation Now
Lake Folahanmi Olawole

Since signing a joint-venture deal with Atlantic Records in 2015, Generation Now (the name comes from a 2004 mixtape Drama and Cannon curated) has risen to the top of hip-hop’s crowded field of imprints and boutique labels by building on each founder’s expertise and investing in artist development from the ground up. In the process, it has signed two of the genre’s biggest 2020 success stories: Lil Uzi Vert and Jack Harlow. “They represent the cross-section of traditional hip-hop artist development and culture and what the kids want to hear,” says Atlantic chairman/COO Michael Kyser of Generation Now’s principals. “They bring decades of experience and knowledge, as well as their unique ability to adapt to the speed and methods that fans want for their music in 2020.”

Generation Now’s road to success has paralleled that of the music its founders loved in their youth. Drama, Cannon and Lake kept in touch after college. And as the 2000s began, Drama made a name for himself as mixtape host to a slew of Southern rap all-stars — Wayne, Jeezy, T.I. — with his Gangsta Grillz series, then expanded his reputation over the next decade with mixtapes for Pharrell Williams, Chris Brown and the late Nipsey Hussle. By 2014, he had landed an A&R job at Atlantic; soon after, he opened his own Means Street Studio in Atlanta, an incubator for budding local talent.

Producing for Drama on Gangsta Grillz, Cannon, too, realized the power of building relationships. He landed credits for 50 Cent, Jeezy and Fabolous, and in 2008 left The Aphilliates to focus on his own production company, hosting Big Sean’s Finally Famous Vol. 3: Big mixtape and creating beats for Jeezy and Curren$y. In 2013, he became vp A&R at Def Jam Records.

Lake’s rap dreams didn’t last beyond college, but a key friendship did. In 2004, he was at a video shoot for Ma$e (whom he had met through a friend at Morehouse), where Cudda Love, Ma$e’s former manager, changed the way Lake thought about his future. “He pulled me to the side and said, ‘There’s all these dudes trying to rap. Try to do business,’ ” recalls Lake. So he dove into learning music management, eventually co-managing R&B star Bobby Valentino for three years — and, later, Drama and Cannon.

On their own, the three had honed a knack for uncovering raw talent while still maintaining tight-knit relationships with creators they had connected with years ago. At their respective labels, say Cannon and Drama, that didn’t always translate to signing the acts they wanted. “We had our hands close to various artists who are now superstars, who we had the opportunity to sign or just had the feeling like, ‘OK, this person is up next. Let’s be ahead of it,’ ” recalls Drama. (He and Cannon declined to name who those artists were.) “We missed on some things, [but] we said, ‘We don’t want to miss anymore.’ ”

The next time opportunity knocked, in 2014, they grabbed it. Driving to an Atlantic City, N.J., DJ gig, Cannon heard an up-and-coming Philadelphia rapper named Lil Uzi Vert on WUSL (Power 99) and, intrigued by his flamboyant lyricism, called host DJ Diamond Kuts to learn more about him. “I went back to Philly to meet Uzi and did some research,” says Cannon, 41. “I noticed people knew about him, but not too much. I just took it back to the squad and told Drama, ‘We need to do this shit for real.’ ”

Generation Now
DJ Drama Folahanmi Olawole

Drama went to Atlantic with a major proposition: forming his own label with his college buddies. “I told them, ‘I don’t do this alone, and my partners are very prominent parts of what I bring to the table,’ ” says Drama, 42. “It was a plan we didn’t even realize was taking shape. I was always campaigning for my guys.” In the meantime, he and Cannon brought Uzi to Atlanta to work on new music, including his 2014 mixtape The Real Uzi (which Cannon hosted). By 2015, Generation Now’s joint venture with Atlantic was signed, along with its blue-chip prospect. In October of that year, Uzi released his debut project on the label, Luv Is Rage — a mixtape executive-produced by Cannon and Drama — and Generation Now’s founders proved once again that they were no ’90s relics.

“I think Uzi was a little different from what people expected to come from Dram and Cannon,” says Lake. “These guys had a certain style of music for over 10 years. I think people were expecting us to come out with a Jeezy-type artist first — somebody street, somebody gangsta — or even somebody from the South. [Cannon] saw the vision.”

Their initial focus on one flagship artist paid off: In 2017, Uzi’s emo-leaning single “XO Tour Llif3” rocketed to No. 7 on the Billboard Hot 100 and set the stage for a monster album debut. Three months later, Luv Is Rage 2 debuted at No. 1 on the Billboard 200 with 135,000 equivalent album units, according to Nielsen Music/MRC Data.

With Uzi’s star rising, Generation Now had the clout to pursue another promising young artist: Kentucky-based Jack Harlow. Drama checked out the then-22- year-old’s Instagram on the recommendation of a friend at Means Street. He was impressed by Harlow’s lyrical dexterity, and he wasn’t the only one: Kentucky engineer KY Engineerin’ (a mixer for 2 Chainz and Meek Mill) had told Lake about Harlow, too. Generation Now met Harlow in Atlanta in 2018 and signed him shortly after. “He’s truthful, and he works his ass off,” says Cannon of the rapper. “He fights tooth and nail for everything.”

By keeping things small, Generation Now had landed two major talents. But that didn’t mean the label was immune to major conflict. In January 2018, Uzi tweeted some advice for fellow artists that fans interpreted as a Drama subtweet: “Sign 2 a major Dont sign 2 a rapper or a Dj ..Its Just Easier When The Time Come For That Fake Shit.” That year, he released just one song, “New Patek,” which peaked at No. 24 on the Hot 100.

In early 2019, Uzi took to social media again with a starker message. “I’m done with music,” he wrote on his Instagram Story. “I deleted everything. I wanna be normal. I wanna wake up in 2013.” He didn’t retire though: That March, he uploaded “Free Uzi” to SoundCloud and Tidal, with lyrics that read like another shot at Generation Now: “I can’t trust none of these n—s, might turn on me/I’m still a millionaire, this shit not hurting me.” On the same day, he announced a management deal with Roc Nation.

The news stunned Generation Now’s founders, who were already confronting backlash from impatient fans for reportedly shelving Uzi’s next album, Eternal Atake — and it also seemed to irk labelmate Harlow. He posted an Instagram shot of himself hanging out with Drama with a caption jabbing at Uzi: “just signed my soul away…. double tap if you can’t wait for Eternal Atake.” Uzi’s response? Posting a pic of Harlow with the artist’s face covered by the clown emoji and the words “Free Uzi” written on his arm.

“I don’t think there was any hostility between the two,” says Lake today. “Jack was realigning himself with us, which meant a lot.” To this day, the Generation Now guys won’t talk about the origin of the apparent feud with Uzi; they say their experience has taught them to take the high road. “That’s a difficult thing to do,” says Cannon. “There have been times where we were biting our nails, wanting to speak on some things. We never spoke on those things.”

Generation Now
Don Cannon Folahanmi Olawole

Uzi never broke his contract with Generation Now. By the end of 2019, he was back to releasing new singles, and in March, the long-awaited Eternal Atake arrived. “We weren’t as hands-on with Eternal Atake in production as we were with Luv Is Rage 2,” says Lake. “We wanted to put it out, and when we got the nudge that it was ready to go, we were just as excited as the public.” The hourlong album turned out to be a magnum opus worth waiting for: It debuted at No. 1 on the Billboard 200 and, in its first week, charted 20 titles simultaneously on the Hot 100 (including all 18 album tracks), making Uzi only the third artist (after Drake and Lil Wayne) to achieve that feat. A week later, the deluxe version Lil Uzi Vert Vs. The World 2 arrived and also shot to No. 1.

In the end, Generation Now’s first big discovery came through for the label. But even while tensions with Uzi unfolded over the better part of two years, the founders stayed busy with Harlow. Throughout 2018 and 2019, they hunkered down in the studio (much as they had with Uzi) to release two mixtapes and start building a fan base. By January of this year, Harlow was set to come out swinging — and he did, with “WHATS POPPIN,” a catchy track highlighting his winning attitude and witty wordplay.

Harlow had befriended Cole Bennett — the 24-year-old Lyrical Lemonade founder and video director known for breaking Lil Tecca and Juice WRLD on his 15.8 million-subscriber YouTube channel — and he tapped him to shoot a video. “WHATS POPPIN” exploded, spawning TikTok challenges, breaking into Spotify’s RapCaviar playlist and earning 108 million YouTube views. Its climb up the Hot 100 was slow, but by July, it hit the top 10 and a week later zoomed to No. 2 thanks to a remix featuring Lil Wayne, DaBaby and Tory Lanez, all of whom hopped on the record thanks to Drama’s efforts.

“The foundation the label has provided has made it a lot easier for me to figure out how I want to navigate the game,” says Harlow. “The three kings have had a huge hand in molding me into a star. They taught me how to move. Their stories and wisdom provide me with endless context and appreciation for tradition.” This winter, he’ll release his debut album — one that Lake isn’t afraid to boldly compare to a contemporary game-changer. “He’s making an album that we think is comparable to [Kendrick Lamar’s] good kid, m.A.A.d city,” he says. “He’s rapping with dope concepts where every beat is amazing. Features you wouldn’t expect.”

As the founders have learned over the past 20 years, building a singular label — one that not only becomes part of hip-hop’s long tradition but also moves it forward — doesn’t simply mean finding another Harlow or Uzi. “We never once tried to sign somebody that sounds like somebody else,” says Cannon. He hopes that if Generation Now follows any prior path, it’ll be akin to Jimmy Iovine’s Interscope Records — a place where Snoop Dogg and Dr. Dre sat comfortably on the roster next to Marilyn Manson. “I think that’s what we’re building,” adds Cannon. “A team that’s comfortable doing what they’re doing and not worried about the time it takes.”

So while Harlow and Uzi continue to shine, Generation Now is investing in its next potential star: Seddy Hendrinx, a Jacksonville, Fla., artist Drama met through his manager Willie Joe. Since signing to Generation Now in 2018, Hendrinx has gained traction with melodic trap records like “LOWKEY” and “Hands Down” that have garnered millions of YouTube views.

As Cannon, Drama and Lake see it, however, their biggest success isn’t a hit or a diamond-in-the-rough artist find — it’s the fact that, in a business built on relationships, they’ve managed to preserve and protect their own. “It’s a very proud thing to say my best friends that I went to college with 20 years ago are my business partners,” says Drama. “I don’t know if it’s rare, but it feels rare, and it’s key to our success. It’s a proud moment. It feels good to be in business with people who were sharing $150 to throw parties.”

This article originally appeared in the Nov. 14, 2020, issue of Billboard.