Show & Prove
Words: Peter A. Berry
Editor’s Note: This story originally appeared in the Spring 2020 issue of XXL Magazine, on stands now.

Bouncing across the stage while filming a performance for The Tonight Show Starring Jimmy Fallon at New York City’s 30 Rockefeller Plaza on a chilly February day, one polite and unabashedly earnest 22-year-old is about to become a rap star. Clad in a white and red varsity jacket—the name of his hometown stitched into its fabrics—the Louisville, Ky. native absorbs flashes of teal and pink light as he introduces himself to a national audience. “For those that don’t know, my name is Jack Harlow.”

He’s not arrogant enough to say the glitzy television debut was preordained, but Harlow isn’t exactly surprised by it. “Since I was 12 years old, I felt like I could get as far as I want, further than where I am now,” he says matter-of-factly as he sinks into an artist’s lounge sofa in Atlantic Records’ Manhattan office the next day. Since unloading his debut mixtape, Finally Handsome, in November of 2014, Harlow has used easygoing charm, conversational flows and spurts of melody to position himself as the most commercially viable rapper Kentucky’s seen in over a decade. His latest single, the JetsonMade-produced “Whats Poppin,” currently sits at No. 84 on the Billboard Hot 100 chart. Its zany, Cole Bennett-directed accompanying video has been viewed over 12 million times on YouTube/Lyrical Lemonade.

His first-ever Hot 100 placement and eight-digit music video views are just the latest steps in Harlow’s near-decade-long journey to becoming the next big thing. Before rocking the stage on The Tonight Show—or even before he performed sold-out shows in his hometown back when he still attended Atherton High School years ago—the Atlantic Records and Generation Now signee remembers falling in love with hip-hop after hearing his mother play the Black Eyed Peas for the first time. While his father, a handyman who prefers country music to hip-hop, didn’t supply his rap habit, his mother schooled him on the sounds of Eminem and Kanye West’s Late Registration. Soon, trips in the Harlow family minivan were helping Jack build an early interest in a future rap career.

Using the basic mic app on his computer, Harlow teamed up with a friend to record their first songs in sixth grade. For those early recordings, the two would alternate; Jack would rap and his friend would beatbox and then vice versa. Despite a skeletal recording set-up and some high-pitch, pre-pubescent vocals that were made fun of by some classmates, Harlow burned the songs onto a CD and began selling them at school. As the rhymes sharpened and his voice grew deeper, Jack transitioned from beatboxing and a mic app to Audacity and GarageBand. By 2014, the football coach at his high school had directed Jack to a neighborhood local with access to a recording studio. Subsequent sessions led to projects like Finally Handsome (2014), The Handsome Harlow (2015), 18 (2016) and some local fame.

The first audio engineers he recorded with noted the technical savvy of the 14-year-old Harlow. “At a young age, it was like I could control my flow...I wasn’t missing the pocket. I had control. I had technique,” remembers the rapper, who was voted both Class Clown and Most Talented for his high school graduating class. He could only choose one: “Most Talented I thought would age the best so I went with that,” he says.

Harlow says his breakout 2017 single “Dark Knight” helped inspire DJ Drama and Don Cannon to sign him to their Generation Now imprint that fall. At the time, Harlow, whose parents had argued with him over pursuing a rap career instead of a college degree, had just moved to Atlanta and was working at a Chick-Fil-A to pay his share of the bills on a two-bedroom apartment he stayed in with two roommates. With quick-fire flows, quotable lyrics and some dance moves he showcases in a carefree music video shot on the Louisville streets he used to roam with friends from high school, Harlow’s buzz reached a new plateau. “It was the first moment I was seen on such a huge scale,” he recalls. “It had virality. It was where I was getting recognized outside of my hometown.”

For his part, Drama, who along with Cannon signed Harlow to their Generation Now imprint at the behest of Harlow’s friend and mentor Finis “Ky” White, noticed a star-making combination of bars and melody. “The first time I heard Jack’s music, his originality and genuineness is what stood out to me immediately,” Drama says of Harlow, who cites André 3000 as one of his biggest influences. “His lyrical ability was crazy and the depth of his melody and harmonies was nothing I had heard from a new artist in a very, very long time. It was very impressive.”

On “What’s Poppin,” which is the Kentucky MC’s biggest single to date, Jack flaunts that lyrical skill Drama speaks of, unloading multi-syllable rhyme schemes and piercing bars with a breathless flow. “We used to share a connection/Now it just feels like it’s wearing and stretching/I’m getting real sick of taking advice/From people that never could stare at reflections (Ooh),” he raps.

After dropping his Gazebo project in 2017, Harlow’s continued releasing new music on an annual basis. His most recent two projects, 2018’s Loose and 2019’s Confetti, have only pushed his ascent. With each month, his number of Spotify streams increases. Cannon isn’t surprised Harlow’s gotten to the space he occupies now. With a Hot 100 single, a new project due out this spring and his Roaring 20s Tour taking off, Harlow is ready to make good on the promise his label bosses saw two years ago. “He is confident and witty, has his own style, a captivating stage presence and his live show is amazing,” Cannon explains. “Jack is very consistent with content, music and engaging with his fan base. Aside from the music being dope, I’ve been around long enough to know what a superstar looks like.”

While Cannon might have seen a superstar, Harlow wasn’t always sure. In the early days of his recording sessions in Atlanta’s Means Street Studio, the then-wide-eyed-teenager wasn’t sure he was the artist the Generation Now bosses imagined. “There were moments of feeling displaced like, Maybe I’m not what I think I am,” Harlow remembers. “Maybe I shouldn’t be in here. Maybe I’m not as good as these other artists.” While he admits those thoughts were fleeting, he knows that they never disappear. He also recognizes the presence of something else. “Doubt creeps in every day,” Jack continues. “And so does confidence.”

Check out more from XXL’s Spring 2020 issue including our Future cover story, in which he speaks on his Life Is Good albumLil Yachty discusses his new album, Lil Boat 3, and the respect he deserves, Van Jones talks about his love for hip-hop, plus there's a brewing, new hip-hop scene in New York and more.

See Exclusive Photos of Future on a Yacht for XXL Magazine's Spring 2020 Cover Story

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