SZA stood triumphantly before a packed audience inside the Crypto.com Arena in Los Angeles for the 66th Annual Grammys. She had just been named Best R&B Song winner for “Snooze,” one of three gramophones she took home that night. Amid a standing ovation, a teary-eyed SZA, who led all Grammy nominees with nine nods, including an Album of the Year nom for the highly acclaimed release SOS (2022), was just trying to keep it together as she thanked her family and team.

But there was one shout-out that especially resonated: Anthony “Top Dawg” Tiffith, founder and owner of SZA’s recording home, Top Dawg Entertainment (TDE). “I feel like it’s an important moment for us as a label,” says the 49-year-old native of L.A.’s Watts neighborhood from his 13,000-square-foot mansion in Calabasas, California. “It’s powerful when you hear Beyoncé and other big stars say, ‘Hey, SZA deserves this.’”

Tiffith, who coined the Top Dawg label after his around-the-way nickname, has garnered a reputation in the biz for making the improbable happen. He gave his brilliant, sensitive artist and Terrence “Punch” Henderson, TDE’s gregarious president and SZA’s manager, ample space and time to retool her genre-defying TDE/RCA set SOS.

The five-year odyssey was well worth the wait. The powerfully candid collection has sold more than 10m globally. SOS now holds the record for the longest-running #1 in R&B Album chart history at an unprecedented 41 weeks. The album’s biggest single, “Kill Bill,” has racked up about 1.7b global Spotify streams, while “Snooze” has amassed nearly 800m.

Tiffith, however, is too busy to bask in the glow of it all. There’s nothing remotely flashy about him. He rocks a trademark red cap and a T-shirt. This is a low-key dude who rarely grants interviews and avoids glitzy hobnobbing.

Tiffith’s journey from storied street hustler to multimillion-dollar music mogul is the stuff of legend on the West Coast. Having watched many of his friends die or get locked up in prison, he knew it was only a matter of time before he would share the same fate. So in 1997 Tiffith turned his attention to the music game, building a recording studio in the back of his home in Carson, California.

By 2004 he had established Top Dawg Entertainment. Tiffith recruited younger cousin and budding MC Henderson to help build TDE, which soon became a safe haven for young local rappers and producers desperately looking for an alternative to the Crips-and-Bloods gang violence that engulfed so many neighborhoods in his beloved inner-city Los Angeles.

Tiffith is a relentless force. He once literally chased down local troublemaker Jay Rock—he was from the same Nickerson Gardens projects in L.A. where Top grew up—who thought he’d run afoul of the imposing six-foot-one ’hood legend. Tiffith made the two-fisted orator TDE’s first signing. Tiffith next landed a gifted kid out of Compton who called himself K.Dot, later known to the world as celebrated hip-hop visionary Kendrick Lamar. Lyrically witty Carson native Ab-Soul and South Central’s charismatic ScHoolboy Q rounded out TDE’s foundational Black Hippy crew.

After a string of underground classics, the meticulous Tiffith, known for his hands-on approach, executive-produced Lamar’s peerless three-album run of Good Kid, M.A.A.D City (2012), To Pimp a Butterfly (2015), and Damn (2017), for which the lyricist extraordinaire was awarded hip-hop’s first Pulitzer Prize. When TDE made the jump to R&B with SZA’s bold 2017 debut, Ctrl, it became a hit with both critics and fans, eventually going triple platinum.

By 2020, hip-hop and R&B had become the dominant genres in the U.S. marketplace. At its peak, Top Dawg Entertainment’s artists accounted for nearly 5% of domestic activity in these genres. Yet when Lamar left TDE to start his own independent music and media hub, pgLang, observers were all too ready to give the company its last rites.

Tiffith, however, wasn’t trying to hear any epitaphs. He and his team ignored the chatter and launched SZA’s transformation into a major global pop headliner. Her current arena-packing SOS Tour has so far raked in north of $95 million.

“He’s not just an owner of a label,” Henderson says of his boss. “Top will come in the studio and will fire off ideas. He shows respect and everybody respects him in return. He’s never been on that tough guy, rah-rah stuff. He treats the label like a real business.”

And in point of fact, Top remains a vital figure in Kendrick’s circle, as evidenced by his presence in the video for the rap giant’s 2024 smash “Not Like Us.”

Here’s the indomitable man in his own words.

How gratifying is it to see an out-the-box R&B artist like SZA elevated to a full-blown megastar?

You know what? We saw SZA’s success early. She had all the potential in the world, it’s just now everyone is getting a chance to see her talent. That’s the exciting part.

It has to be surreal witnessing SZA, who started out as a cult artist in 2013, performing in front of 20,000-plus people on one of the most talked about international tours.

It is. You gotta think about it: On SZA’s first tour we were doing rooms of 2,000 people. The SOS Tour came right after Ctrl. We went from that to doing arenas. That speaks to just how in-demand she is and how much people have connected with her music.

Do you see SZA creating a blueprint for other TDE artists looking to merge R&B, hip-hop, alternative soul, and pop?

She’s carrying the torch for the label. But there’s no blueprint, because each artist is different.

Take us back to the days before the founding of TDE in 2004. You set up a recording studio in your family home in 1997. Was music something that you always considered a viable career path?

To tell you the truth, I wasn’t into making music like that in the beginning. I was too heavy in the streets trying to get rich. I knew the hustle game wouldn’t last forever, and after getting the type of money I was getting from the streets I knew a 9-to-5 job wouldn’t work for me. I built the studio as my backup plan for whenever the time came for me to get out of the streets. I must say, music was the best backup plan ever. It changed my life and many other lives.

So you got into the music business on a whim?

Naw, my uncle Mike Concepcion was heavy in the music business. I watched him have a lot of success with artists like Blackstreet, MC Hammer, Rome and others. He also produced The West Coast Rap All-Stars’ peace record, “We’re All in the Same Gang.” He’s the one who sparked the idea of me getting into the music business.

So by 2008, Jay, Kendrick, Q, and Ab are all signed, setting the foundation for TDE, and you signed a label partnership with Asylum/WMG. But there were some stumbles early; more specifically, the rollout for Jay Rock’s debut Follow Me Home was abruptly shut down following a regime change at the label. What did that experience teach you?

That experience was terrible when we were going through it. But looking back at it, that’s what got us focused on our hustle. When we signed our first major deal, we thought that that was it. We got a deal—we’ve made it! But the truth is that’s when the real grind starts. We didn’t know that back then. It was all trial and error. Our whole goal was to get signed and make these kids superstars.

You mentioned TDE’s goal early on was birthing superstars. One superstar who graduated from the label is Kendrick, arguably the most celebrated hip-hop artist of his generation. What are your fondest memories of working with Kendrick on his final TDE album, Mr. Morale & the Big Steppers?

To be honest, the whole process of making that final TDE album was sad for me. After all these years together with great success, I’m about to watch my son pack up and leave. These kids were eating at my house. They were using my house as if it were theirs and would come in, record and feel free, like they were home. There’s always been a deeper relationship than just music. That’s where it still is today with Kendrick. It’s just that now he is doing his own thing. He’s stepping out as a man and building his own company, just how he watched me build mine.

What’s the best advice you would give to aspiring executives looking to break into the music business?

The best advice I could give to someone following in my footsteps is to hustle like you are broke. That’s the TDE motto. Even when you reach a certain level of success, you have to keep going like you don’t have nothing.