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.

When Henderson pulled SZA from a scheduled 2023 performance at the MTV Video Music Awards after she was snubbed in the Artist of the Year category, the fiercely protective Tiffith called the producers out. (The incident recalled another headscratcher of an awards-show moment for TDE, when overwhelming favorite Kendrick Lamar lost out to white pop-rapper Macklemore in all three rap categories at the 2014 Grammys.)

“I stand behind Punch and the decision to pull out of the VMAs 100%,” Tiffith told HITS in September of last year. “MTV wasn’t even willing to discuss why SZA wasn’t nominated for Artist of Year. If we aren’t even worth talking to about it, we don’t need to be there. She gave the world a great body of work and we will not allow any disrespect.”

“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.”

With the buzz-heavy Doechii, fresh off her RIAA platinum hit “What It Is,” and Grammy-nominated SiR making noise, plus long-awaited albums from Jay Rock, Ab-Soul and ScHoolboy Q on the way, Tiffith is ready to lead TDE into its next major chapter. 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.

We’re hearing from a lot of people that SZA wasn’t properly rewarded by the Grammys, and many feel she should’ve won Album of the Year. What are your thoughts on all that, and on the Grammys generally?

This Grammy BS is nothing new to me. I watched Macklemore beat out my guy Kendrick, Drake, Kanye and JAY-Z for Best Rap Album. It’s been a lot of bad moments with the Grammys, and this is another one. I definitely think SZA should have won AOTY, and that’s no disrespect to anyone else. It’s obvious the system needs to be fixed. Like my guy Hov said, referencing Beyoncé, “There is a young lady who has more Grammys than everyone and has never won AOTY.” I need somebody to make that make sense before next year’s voting starts.

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.

TDE also found success with the development of newcomer singer-rapper Doechii and singer-songwriter SiR. What did you see in those two particular artists that gave you the confidence that they could carry the flag for TDE?

I thought they had all the talent in the world to go as far as they wanted to go. We look for all our artists to be original… to say something.

Doechii has earned comparisons to hip-hop legend Missy Elliott, who rhymes as well as she sings, and SiR is a throwback to the neo-soul vocalists of the past yet has a quirky feel to his presentation. I would venture to say that those two are not your run-of-the-mill A&R sessions.

You can’t put them in a box. SiR represents that traditional R&B that we all know and love and grew up on. He has that soulful voice but the stuff he sings about is real—it’s raw, different. And Doechii is an all-around artist and entertainer. I’m very excited about what the future holds for them.

UMG recently removed its entire music catalogue from TikTok. What’s your take on the current battle brewing?

Everybody is still trying to figure it out, but we hope whatever they do is best for the artists. Streaming deals are still new, so we’re all scrambling. It used to be simple: You’d go to a record store and give them your $10 for an album. Now you’re paying for a music subscription. For $10, you get access to nearly every song that was ever made.

We’re in a brave new world.

Right. The terminology has to change. Because I don’t even think we are selling records anymore.

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.

Punch told me that no one on the team knew how to work the mixing board. That’s pretty hilarious.

Yeah, man. I used to come in the studio and watch this guy Co-T mess around on the board for hours. After he left, I would go in and mess around. It got to the point where I actually learned how to record and mix a little bit. After that, I taught Punch and we were on our way.

That studio also kept a lot of kids like Jay Rock, Kendrick Lamar, Ab-Soul and ScHoolboy Q off the streets. Did you see a lot of yourself in them?

I did, especially Jay Rock. Our studio became the home for everybody around the neighborhood. I can’t tell you the first song I worked on, but Jay was the first to officially sign with TDE. What drove me to him was just the first time I heard his voice. You would have thought he was six-nine, 300 pounds. But here was this little skinny dude walking out of the booth! I just wanted to show all of them a better way. If we had more outlets, there would be more things for these kids to do instead of getting involved with the streets.

You mentioned that you were not necessarily serious about recording early on even when you built your studio. Was there a moment that made you say, “Okay, it’s time for me to leave the game behind for a better life and get serious about this music thing”?

Man, when the Feds came knocking on my door, I knew it was time to get up out of there. On top of that, I never felt like hustling was a forever thing for me. I knew that I was doing it as a means to better myself and my situation. I think about where I’ve come from all the time. There were many situations on the streets that could have caused me not to be here today, but we made it through.

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.

How would you describe your relationship with the majors today?

We have great partnerships with the majors. They know what we bring to the table. It’s an unspoken thing: We are going to do what we do, and you do what you do, and we will all flourish.

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.

I find it interesting that as soon as Kendrick left TDE all you heard from the critics and fans was that the label wouldn’t survive without its franchise superstar. How gratifying was it for you personally that you were able to silence the doubters?

We are always confident in what we are doing in terms of our vision. But yeah, we heard a lot of that talk. It’s a lot quieter now. But we are a real record company. It doesn’t fall on the shoulders of just one person. We are going to keep turning these records out and keep going.

TDE is known for taking an old-school, hands-on approach when it comes to developing artists. How do you view the state of the A&R in today’s business?

There are a few good A&R people still out there, but labels hurt their position by relying too much on analytics and not seeing the talent in the artist. TDE came in doing everything from top to bottom. As far as A&R-ing, we have been doing that since the beginning. We just didn’t know what we were doing was called A&R.

Artist branding has become a huge part of the business. Do you advise your talent on their branding choices?

We give our artists the freedom to make their own branding decisions.

TDE also prides itself on being a very tight, family-oriented company. Can you speak about some of the people behind the scenes who have contributed heavily to the label’s success?

On the executive side, of course, there’s myself and Punch. Then we have Moosa [Top’s son, Anthony “Moosa” Tiffith], who is also a President at TDE. Moosa discovered Doechii. Josh Binder, our attorney. Just the whole TDE staff in general: Manny Smith, Keaton Smith, Brandon Tiffith, Matt Miller… there are too many people to name. I don’t want to leave anybody out.

Punch said that during your hustling days you sported a Jheri curl, an L.A. Raiders cap, looking like a member of N.W.A.

Punch was my favorite little cousin. I used to go to all his football and basketball games. I did everything with him. When I was a kid and he was a baby, I used to push him around in the stroller. Everybody mixes us up, but we look nothing alike.

Last December, Jay Rock had fans rushing to social media when he announced on New York’s Power 105.1 that Black Hippy would have its long-awaited reunion on TDE’s forthcoming compilation album. Are we finally going to witness Jay, Kendrick, ScHoolboy Q and Ab-Soul together again?

I don’t know. It’s really up to them at this point. That’s something I would love to see—and of course it’s something that the fans would love to see. The issue has always been getting everybody in the same space at the same time. They all have their separate careers and are moving differently. But it’s really up to them.

TDE has a flood of releases set for 2024. What releases are you most excited about?

Everything. 2024 marks the 20th anniversary of TDE. We got SZA coming with a deluxe album soon. We have Jay Rock and Ray Vaughn gearing up. We got ScHoolboy Q and Ab-Soul coming, SiR coming, Doechii coming. I’m excited.

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.