‘Damn, Kendrick bro, if you just stay out of jail and stay alive, you’re gonna make it.’ The words that literally came out of my mouth were ‘Don’t go to jail. Don’t die.’ ” Sadly, prison and death beset many of their friends.

And it wasn’t like Kendrick didn’t grapple with his own challenges: At age sixteen, he started running with the wrong crowd—partying and drinking alcohol. It was really just kid shit, the same thing teenagers had done for generations. But given Kendrick’s neighborhood and family history, his behavior foreshadowed a possible life of crime and gang affiliation. Kenny wasn’t having it; he’d come too far to watch his son fall victim to the same habits. “My father said, ‘I don’t want you to be like me,’ ” Kendrick told Spin in 2012. “He said, ‘Things I have done, mistakes I’ve made, I never want you to make those mistakes. You can wind up out on the corner.’ He knew by the company I [kept] what I was gettin’ into. Out of respect, I really just gathered myself together.” Kendrick adored his father and his loving, no-nonsense attitude. The two bonded over a love of Tupac and gangsta rap. Kenny let him experience triumph and tragedy and was there with real talk when Kendrick lost his way. He playfully coined his dad’s advice as “intelligent ignorance.” Many of his friends didn’t have active fathers at home, but Kenny and Kendrick shared a close bond full of hard lessons and growing pains. He’d caution teenage Kendrick against going with his friends to burglarize houses in the neighborhood, and would be there with a swift “I told you so” when police accosted them before the crime unfolded. At times, Kenny tried to steer Kendrick’s friends away from doing wrong. But because Kenny wasn’t an actual father to those kids, the advice simply wouldn’t stick, and some of them wound up in jail as a result. Of course, Kenny wasn’t impeccable—he was a flawed human like the rest of us—but he had a good heart and truly wanted to do right by people.

Having supporters like Matt Jeezy and Mr. Inge helped Kendrick. They saw a light in the young man and helped him nurture it, even if it took the young poet a little while to fully embrace his truth. “Thinking back to when we were walking home from Centennial that one day,” Jeezy wistfully recalls. “Look at him now, man. Look at him now.”

In hip-hop, it’s common for rappers to brag about themselves. It’s not enough for them to simply say they’re the best; by the end of the verse, you should know they can walk on water and turn it into wine. Or you have to be the toughest dude ever: Mess around if you want, you can catch a bullet, too. So Kendrick’s earliest rhymes aren’t surprising; he was imitating what he’d heard others do since the dawn of hip-hop culture, some thousands of miles away in the Bronx, long before he was born. On YouTube, there’s a video clip of teenage Kendrick, cross earrings in each lobe, spitting aggressive rhymes while his friends stand directly behind him. He’s in the middle of a cypher, and on certain punch lines, he looks away and smirks, as if he knows he’s the best. He tugs the hood of his sweatshirt, letting it rest sluggishly on the crown of his razor-sharp waves. He studies the lens, gaping at it with the confidence of a seasoned veteran. This was exercise for Kendrick, who, at this stage of his career, wanted to come off as a street guy. “Creep into ya house, you hear footsteps slowly as I tippy-toe,” he asserted through squinted eyes and gapped teeth. “I’m wise like my pops but I’m young, muthafuckas / I’m the one, muthafuckas / Plus around hustlers, you want it? They can serve you like a butler.” The claim sends his friends into a frenzy, so much so that Kendrick can’t even finish his verse. Their reaction proves that he is very much the people’s champion, and that those closest to him truly have his back. He was born to the streets, so his rhymes feel authentic. In those days, maybe he would run up in your house.

Still, there was something missing from Kendrick’s flow—and that was Kendrick himself. He rapped under the name K-Dot, his fire-spitting alter ego. K-Dot wasn’t about uplifting communities; he wanted to decimate everything in sight. The young man had all the technical prowess, the complex sentence structures, and the natural cadence, but he didn’t sound free. He was playing a character, and the fastest way to get noticed was to sound like the higher-profile rappers who dominated hip-hop. He wasn’t playing the long game yet. He hadn’t realized that the truest path to immortality was to be his fully authentic self. Good, honest music has this way of reaching the right ears; it finds people exactly when they need to hear it. Though Kendrick would come to understand this years later, back then he seemed eager to ascend to the top before he had a full grasp of what it took to remain there.

To understand Kendrick’s approach, you have to understand hip-hop’s period of transition at this time. The year was 2003, and acts like 50 Cent, OutKast, and the Diplomats loomed large in the music industry. Hip-hop was a global business, and rappers with the biggest pull were tapped to sell everything from malt liquor to high-end clothing. “Cool” was in fashion, and no one was cooler than Shawn “Jay-Z” Carter, a poised, slick-talking MC who went from selling crack cocaine in East Trenton, New Jersey, to becoming the most popular mainstream rapper in the world. Jay-Z wasn’t only a rapper; he was a paragon of business, lyricism, and swagger. “I’m not a businessman, I’m a business, man,” he once claimed on Kanye West’s song “Diamonds from Sierra Leone (Remix).” He was a king who’d spent the past five years

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