The green and pink pastel panties sell for $10 apiece. He released The Handsome Harlow EP in November of his senior year, and another T-shirt has its minimalist art: hair depicted as smoke swirls above the glasses. One of the T-shirts at the merch table features the 18 cover art: Harlow striking The Thinker pose in nothing but gray boxer-briefs and his signature black-framed Brooks Brothers eyeglasses. Harlow - who had meetings with Def Jam Recordings and Atlantic Records during his freshman year at Atherton High School, class of 2016 - released his most recent mixtape, 18, less than a month after graduating. “It just obviously makes it worse when neo-Nazis say it.” “Like they haven’t always been the shoes of white people,” Harlow says. A white-supremacist website claimed the company made “the official shoes of white people.” Photos of New Balances on fire - actual fire, not dope fire - or impaled with knives made the rounds on social media. Harlow owns more than a dozen pairs of New Balances, every color in the spectrum, but the brand got press recently because a higher-up at the company made favorable comments publicly about then President-elect Trump. All night he has been wearing plastic grocery bags over his New Balance sneakers, which he buffed with a toothbrush and a laundry detergent-water mixture while choosing his outfit for this evening: khakis with cargo pockets, and the Nautica over a hockey jersey. Moments before parking on the side of Headliners, Harlow pulls up the hood of his ’90s-era, neon-accented Nautica parka, to conceal his identity from the kids waiting to get inside and to protect his corkscrews of brown hair from the raindrops. The car lists across the double yellow line. “It’s gonna be so lit!” says Wyatt, a photographer and self-described “creative-director type” with blond locks that would make a Disney princess jealous and high-top sneakers that say “Fuck Em” all over. Yep: crispy.) His longtime friend Urban Wyatt is riding shotgun and asks to see the screen too. “This show is gonna be fire!” (Quick attempt at translating: “Fire, dope and crispy are synonyms,” Harlow says. “Oh, shit!” he shouts, his face transforming into a real-life toothy and dimpled smiling emoji. Harlow swivels his head and snatches the phone. A couple hundred fans are sardined toward the front. “Let’s see the crowd!” Craighead says to O’Bannon, who’s already onstage. In the backseat, Harlow’s roommate Chauncy Craighead, who goes by Ace Pro, is on FaceTime with DJ Ronnie O’Bannon, aka Ronnie Lucciano, aka Lucci. “He’s actually kind of adorable,” anchor Dawne Gee said after the segment, “but I don’t know if a rapper likes to be called adorable.”
Which is saying something, because he has even rapped about ’Doba, as he sometimes calls it: “Pinto beans in my burrito, roll it up and shove it in me.” On his phone inside the restaurant, he pulled up a WAVE-3 interview he’d done to promote tonight’s gig. Harlow and some friends are returning to Headliners Music Hall after a pre-show dinner at the Highlands Qdoba, though Harlow didn’t eat because his stomach typically won’t let him before a show.
The speedometer’s needle ticks toward 50, 15 over the 35 mph speed limit. Jack Harlow is in the driver’s seat of the 2005 Pontiac Grand Prix he bought off his grandparents for $2,000, lead-footing down dark and drizzle-slicked Cherokee Parkway on the way to his Thanksgiving Eve concert. For the next six years, her son would need to work on rapping for four or five hours every day. With Jack’s 18th birthday as a deadline, she did the math. “Mom,” he said, “how do I become the best rapper in the world?” His mother had just read the book Outliers, which popularized the theory that the secret to greatness is 10,000 hours of practice. As his parents pulled into the driveway, Jack Harlow had a question from the backseat.