Somewhat inexplicably, he’d made a fan out of Lady Gaga, who by 2012 had become a mega pop star with the type of box office fame we hadn’t seen since Madonna in the mid-1980s. From the outside, the friendship felt odd: she was an eccentric personality who had worn a meat dress to the MTV Video Music Awards just two years prior. Kendrick was introverted, didn’t like drama, and was more content living in his own head. Nonetheless, Gaga came to the festival in a mini motorcade, and pulled up to the rear of the Blue Stage, where he was performing. There were rumors that she might even perform with him. Gaga’s appearance was a big deal for Kendrick and the festival itself: Pitchfork was known for attracting niche artists with sizable cult followings, not ones with Gaga’s gravitational pull. “We didn’t have any notice of her showing up and being sidestage until a half hour beforehand,” Schreiber recalls. “She just rolled up and there she was.”
Rappers with bigger names and bigger budgets couldn’t land a Gaga cosign, so for Kendrick—a nascent MC who was anti-industry—to garner that level of interest meant he really had something worth hearing. That he didn’t care about the fame likely attracted Gaga to his music. “She’s a regular person,” Kendrick told Pitchfork. “We became friends off of the genuine love for the music. She just hit my phone one day and said that she had a respect for the hip-hop that I was doing, that it wasn’t like anything she heard on the radio. Then chemistry collided from there.”
The energy was hectic backstage at the festival. Pitchfork staffers had to somehow sneak in one of the biggest pop stars in the world without disrupting Kendrick’s set. “By the time the show happened, you could see her sidestage jamming out to each song, but very clearly not planning to come out,” Kaskie recalls. “After some talks with [my business partner] Mike Reed and some folks on their team, it sounded like Gaga saw his set as ‘his moment’ and didn’t want to take the spotlight off of him. I thought that was fucking awesome of her, because it definitely would’ve made the show all the more frenzied.” There was something electric about Kendrick, something engaging yet somewhat foreign. No one could figure him out or make sense of the connections he made in such a short time. And because the rapper didn’t divulge a lot when he spoke made him even more mysterious, and thus, more intriguing. Two questions followed Kendrick as he rose up the ranks: Of all the budding lyricists in the world, how did he get Dr. Dre’s cosign? And just how the hell did he get Gaga’s attention?!
In the whirlwind that his life quickly became, the rapper struggled to reconcile his ascendance. Yet to those closest to him, the love wasn’t surprising at all. He was a genuine dude who had worked incredibly hard in silence to finally reach this point. People like Kendrick don’t stop to smell the flowers or revel in the love that they’ve rightfully earned; they’re obsessed with getting better. Good work is the foundation of success, and even if Dave Free, Sounwave, “Top Dawg” Tiffith, Dre, or Gaga hadn’t seen greatness in Kendrick, he was destined to win anyway. He had his head on straight; he wasn’t going to cheat the process. “He put in his ten thousand hours to be an ascendant master at his craft. He’s incredibly disciplined,” says vocalist Anna Wise, one-half (or one-third, depending on who was in the group) of Sonnymoon, an alt-soul and bedroom pop outfit of which Kendrick became a fan after watching clips on YouTube. Kendrick reached out to Wise because he liked the different characters she portrayed in her music. Within the course of a song, she could flip her falsetto from sultry to cartoonish. The two sang on “Cartoon & Cereal” and became frequent collaborators.
The genesis of Kendrick’s legend can be traced to that stage, in Union Park, on a sweltering ninety-two-degree day on Chicago’s North Side, where fans chanted his name with a vigor that they hadn’t before. Somewhere along the way, Kendrick became a household name; they knew these songs and yelled the rapper’s bars back to him when his DJ, Ali, cut the instrumental for their voices to shine through. Section.80 tracks like “HiiiPoWeR,” “Hol’ Up,” and “Fuck Your Ethnicity” had suddenly become cult favorites. “I remember watching him just cut loose,” Schreiber recalls. Fans—and, yes, even Lady Gaga—saw Kendrick sweat through a forty-five-minute set and become a leading man in real time. In the summer of 2014, Kendrick returned to Union Park and the Pitchfork Music Festival, this time as one of its three headliners. This time the money was much better (roughly three hundred thousand dollars) and the stakes were much higher. Plus, Kendrick was earning serious clout. “We wanted him
