Tiffith constructed a studio space in the rear of his Carson house, and stocked it with high-end recording equipment as a way to attract big-name rappers. He also wanted it to be a hub for burgeoning talent, though it wouldn’t be that right away. The streets still tugged at Tiffith and he abandoned the space not long after he furnished it. “It was inactive,” Tiffith’s cousin Terrence “Punch” Henderson Jr. told XXL in 2012. “Top Dawg was doing Top Dawg things.”
Tiffith named the company after himself, calling it Top Dawg Entertainment. Once he fully dedicated himself to music, he started working with a producer named Demetrius Shipp, who had made his reputation as an in-house beatmaker for West Coast powerhouse Death Row Records, and whose son, Demetrius Shipp Jr., would later play Tupac Shakur in a big-screen biopic. That connection helped legitimize Tiffith’s operation; soon after, rappers like The Game and Juvenile (a southern rap legend who helped put New Orleans hip-hop on the national map) ventured to the upstart studio. “Game came through before he really kicked off,” Tiffith told XXL. “Juvenile came through there, and a couple of other rap dudes came through. We were just trying to sling tracks to them.” Tiffith was trying to win like everyone else, and his work ethic made him an immediate force in the underground scene. He wanted to get his label’s music to anyone who’d listen, and his experience as a hustler gave him the fortitude to deal with the ups and downs of life in the industry. Dave Free was equally tenacious; in Tiffith’s Top Dawg Entertainment, he saw a man who was incredibly serious about building and sustaining a viable company. He had the connections and the willpower to win, and Free needed to get Kendrick’s music to Tiffith however he could.
One day, Free—then working as a computer technician—got a call from Tiffith to fix his computer. A few minutes after Free arrived, he realized he couldn’t salvage the mogul’s machine but didn’t want to squander this opportunity. Who knew if they’d be in the same room together again? As Free worked, or at least looked like he worked, he played Kendrick’s music loud enough for Tiffith to hear it, and by the end of the job—when Free finally admitted he couldn’t repair the device—Tiffith was eager to hear more. Except, next time, it would have to be in a live setting where he could assess the bars for himself. Kendrick had to freestyle for Tiffith and wow him on the spot.
This was the shot Kendrick had been waiting for; his first grand moment. Once in the vocal booth, Kendrick freestyled off and on in Tiffith’s studio for what seemed like forever: “Top said, ‘Let me see if this is really you,’ and I was just freestyling, rapping whatever came into my head, sweating for two hours.” Tiffith was so taken by Kendrick’s ability, that—at just sixteen years old—he was fully grown as a rapper, even if he didn’t know how to write an actual song yet. As Tiffith told Vibe: “I put him in the booth and put this double time beat on, trying to throw him off. He went in there and started going off! So I’m trying to play like I’m not paying attention. He notices I’m not moving and starts going crazy. So I look up and I’m like, ‘God damn. He’s a monster.’ So the next day I had a contract for him.” Kendrick’s signing with Tiffith raised a few eyebrows, though. The rapper grew up on the west side of Compton, and the local Pirus had beef with the Bounty Hunter Bloods, of which Tiffith was a member. “For Kendrick to sign with a dude from the Bounty Hunters and from Watts, people were looking at him like, ‘What are you doing?’ ” says Matt Jeezy. “They were looking at it from the wrong perspective.”
By 2004, there wasn’t a true King of West Coast Rap like there had been in years past. Ice Cube was focused on acting. Dr. Dre was more concerned with running his record label, Aftermath Entertainment, than putting out his own music. Snoop Dogg was still around, but he was more preoccupied with pimp life than hip-hop. In a 2006 Rolling Stone article, he spoke of how his marriage almost ended due to the lifestyle, until a few pimps at a Players Ball in Detroit told him to go home to his wife. So the icons were preoccupied, leaving the field wide open for new talent to