Though he was born in Louisville, Harlow credits the few years he spent in Shelbyville, Kentucky, a town of about 16,000 some 30 miles outside the city, with helping him discover his knack for reading and writing. Removed from electronics and video games, he relied on his imagination for entertainment, and began to pen short stories.

By the time he got to middle school, he, his parents, and younger brother had returned to Louisville, where he traded short fiction for lyrics. Even then, as he was shaping his sound, he was keen on the idea that rapping would become more than a hobby. He burned 40 copies of Rippin’ and Rappin’, a mixtape he recorded with a friend, and sold them to his peers at Highland Middle School for $2 each.  

While his goal was to make it big, Harlow also wanted to become an example of his city’s musical talent. “I’d hear Outkast, or I’d hear Drake, or I’d hear Kendrick Lamar talk about where they’re from and rep it. And I was like, ‘Who’s going to do that for Louisville?’” he says.

Suddenly, after Harlow reached high school, someone was. “Bryson Tiller comes out. I’m in awe. I’m inspired. And I’m totally jealous. And I’m just like, ‘Oh my God, this guy got it.’”

Eventually, the two would connect. In 2019, Harlow and Tiller collaborated on “Thru the Night,” a light, bouncy production by The Understudy. The two reconnected on “Luv Is Dro,” alongside Static Major, another Louisville artist, on Thats What They All Say, but they’ve yet to jump into the joint project Tiller says they discussed. “We never got around to doing it, just because I wasn’t in the right headspace,” Tiller explains. “But I think now, if [he] and I linked up, it would be super dope,” he says. “We definitely have to make something happen in the future.” 

Tiller is a fan of both Harlow’s music and how he moves. “Jack did his own thing,” he says. “Never asked for a handout. He just got back in the studio and worked harder.” And that example is good for the scene as a whole. “He loves the city just as much as I do, if not more. And, man, he’s inspiring the next kid in Louisville to do it.”

Harlow is confident that kid exists. “I know there’s hidden gems in Louisville,” he says. “I know there’s kids that are growing up and seeing me, Bryson, and [EST] Gee, and [saying], ‘Hey, I want to make music, too.’ I’d love to be somebody that can help facilitate that for them, and somebody that can put them in a studio.”