Hip-Hop 50: Why Innovation Still Rules Lil Wayne’s World

Five years ago, Lil Wayne sat down in his Miami recording studio and spoke in depth with Billboard for the first time in almost a decade. The trailblazing rapper and entrepreneur stood at a crossroads: On the verge of releasing what he had declared would be his final album, Tha Carter V, he had finally settled the three-year lawsuit against his former label Cash Money that had delayed the project’s release and just been awarded sole ownership of the Young Money imprint he had launched in 2003.

So as Aug. 11 — the 50th anniversary of hip-hop — fast approaches alongside Young Money’s own 20th birthday, it’s fitting to be sitting down with Lil Wayne once again. One of the genre’s most innovative and still influential artists, the 40-year-old Louisianian occupies a unique vantage point, forged during a now nearly 30-year journey that began in 1997 with the New Orleans group Hot Boys and soon grew into a multimillion-selling solo career. And that’s not counting the still-growing list of hit collaborations he’s had with a diverse array of fellow hip-hop and R&B artists — including Drake, Nicki Minaj, Future, 2 Chainz, Chris Brown, Mary J. Blige and Lil Baby — as well as other intrepid pairings with artists up and down the genre aisles: Madonna, Ariana Grande, Justin Bieber, Imagine Dragons, Fall Out Boy, Romeo Santos and Shakira, among others. In the course of hip-hop’s own evolution, Wayne’s career is a bridge between then and now, between the genre’s storied, hard-won past and its next-gen, global future.

Young Money Records executive vp/GM Karen Civil, who began running Wayne’s label and several additional portfolios — including his rum brand, Bumbu, and his underwear line, Ethika — in March, says that she also looks at him “as a tree, a foundation. Through the years, we’ve seen different branches blossom, from Nicki and Drake to his businesses, including Young Money, and his relationship with [label president] Mack Maine. A lot of people know Drake and Wayne. But he’s set up so many other people — Tyga is one — who have given him his flowers, like, ‘You’re the reason I rap.’ Those moments mean a lot because he loves to see people around him win.”

Producer-rapper Swizz Beatz has personally witnessed Wayne’s evolution from the time when, as he recalls, they were both “the youngest ones” on the Cash Money and Ruff Ryders tour in 2000. “I knew he was special then, and he’s definitely special now,” continues Swizz, who has collaborated with Wayne for more than 20 years. “It takes a special eye and ear to see a Drake before he’s Drake or a Nicki before she’s Nicki … or the many other artists he’s been involved with who are some of the biggest artists alongside himself to date. That comes from his investment of time, his eye, energy and business sense. He’s responsible for this generation of music.”

Before he could provide a foundation for others, Wayne had to build his own. Over his career, he’s notched five No. 1 albums on the Billboard 200 and 12 top 10s. Tha Carter III, released in 2008, spent three weeks at No. 1 — making it the Wayne album with the most weeks at that perch — and has racked up 221 weeks total on the chart, the most of any of his releases; in September 2022, the RIAA recertified it at eight times platinum.

On the Billboard Hot 100, the five-time Grammy winner has claimed a total of 25 top 10s — including gems “A Milli”; “She Will,” featuring Drake; and “6 Foot 7 Foot,” featuring Cory Gunz — and three No. 1s: “Lollipop,” featuring Static Major (Wayne’s first RIAA diamond track, certified in December); Jay Sean’s “Down,” featuring Wayne; and DJ Khaled’s star-studded “I’m the One,” which, along with Wayne’s guest spot, also features Justin Bieber, Quavo and Chance the Rapper. With 185 total Hot 100 entries — up from 138 just five years ago — Wayne has the fourth-most songs on the chart ever behind Drake, Taylor Swift and the Glee cast.

“Wayne is definitely somebody who continues to create his own blueprint from rap to rock,” says Civil. “I just love the fact that he doesn’t put himself in one category. He continues to reinvent himself and do new things — like becoming a professional skateboarder at 40. He doesn’t put an age limit on things. He doesn’t allow a title, a job or one career set to define him. Seeing the plethora of different people, from [Lil Uzi Vert] to YoungBoy [Never Broke Again] to others who are creating their own genres and sounds, is a testament to Wayne creating that lane.”

And it certainly no longer looks like the ever-busy multihyphenate — who has released an album and two mixtapes since Tha Carter V — will stop recording any time soon; “retirement be damned” seems to now be his motto. According to Civil, Wayne has “quite a few singles” in the pipeline as both lead and featured artist. He and 2 Chainz are currently collaborating on ColleGrove II, the sequel to their 2016 collaboration. Though no release date has been set, Tha Carter VI is also in the works. Wayne recently wrapped 30 dates on his Welcome to Tha Carter Tour, where Drake, Chance the Rapper, Cam’ron and 2 Chainz made special appearances.

And he was in his element opening the ESPY Awards in July with an apropos performance of his 2008 hit “A Milli.” “He was being a true artist, rearranging the words to the song to make sure that it was curated to the event,” Swizz Beatz notes. “I thought that was genius.”

Meanwhile, Wayne continues to develop hip-hop’s next generation of talent, working with Civil and Maine to build his Young Money roster, which includes Allan Cubas, Drizzy P, Euro, Jay Jones, Lil Twist, Mellow Rackz and Yaj Kader.

“Wayne is the ultimate outlier. There was nobody in the history of the genre who sounded like him, looked like him, or released music like him. Everybody caught his wave and just tried to hang on for dear life,” says Republic Records founder and COO Avery Lipman (Young Money is distributed through Republic/Universal Music Group.) “It goes without saying he’s one of the greatest artists of all time, but he’s also one of the most visionary businessmen this industry has ever seen.”

It’s a humble, humorous, polite (“thank you, Miss Gail”), self-deprecating and brief, to-the-point Lil Wayne who sits down once again today with Billboard — this time in West Hollywood — to reflect on his legacy and hip-hop’s future against the backdrop of the genre’s 50th anniversary. With a disarming and sly, diamond-studded grin, Wayne underscores his deep-rooted love of hip-hop. “In my mind, every single time I say the word ‘work,’ I ask God to forgive me,” he says. “Cuz I know this has never been a job. It’s just a dream come true.”

Looking back on your career thus far, what does this momentous anniversary mean to you — and to hip-hop itself — since naysayers initially dismissed the fledgling genre as a fad?

I think it probably means more to me than I even know, because I am still in it, a deep part of it, and I’m still learning every day. Hip-hop will never be over. But I also think that maybe down the line, I’ll be able to answer that question better because I don’t think I know how much it means to me yet — because it means that much.

You signed with Cash Money before you were even a teen. Did you know that early that you could build a career as a rap artist?

I’ve been rapping since I was 7, actually. And I signed my deal when I was 11. I didn’t think about nothing else other than “We about to be the biggest everything.” (Laughs.) Like, I’m about to be this … I’m about to date her. I’m about to do … (Laughs again.) I was a kid, you know? It was like, what are you going [to want] for Christmas? As far as unforgettable moments go [back then], I would say that was probably my first time grabbing a mic as a kid at a block party, breaking my fear and rapping stuff that I had rapped in the mirror for, like, thousands of hours the night before.

So given your early vantage point, what are the biggest changes you’ve seen happen in hip-hop?

Right now is the time where I see the most change in our genre, because back then, I think it was just progress more than change; progression from what was already set before us and also us honoring what was set before us. But now it’s not that no one’s honoring what was before them — it’s just that the world has changed thanks to social media. There was no such thing as social media when I started doing this. But social media has changed the genre and opened doors. That’s definitely what helped contribute to its going global. [Social media] is good and bad.

Want to give examples of the good and the bad?

No. (Laughs.)

What has been the hardest part of your journey?

The hardest part for me is not being able to do [my music], for whatever reason. Not being able to record. Not being able to tour or do a show. That’s always the hardest part.

What one career lesson have you carried along since the beginning?

Never, never stop learning. That’s how you humble yourself. Humility goes a long way and it’ll keep you learning. I just try to get better and better and better.

Did you ever subscribe to the notion that hip-hop is only a young man’s game?

No, never. Because when I was growing up, all the rappers were way older than me. So I don’t know what that notion or narrative was, because it was never a young man’s game to me. I’ve always felt I had to fight my way in when I was a young man.

You’ve mapped a blueprint in terms of musical innovation and entrepreneurial pursuits like your Trukfit fashion line, the Young Money APAA Sports agency, the cannabis brand GKUA Ultra Premium and other business ventures. How do you perceive the role you’ve played in that aspect of rap’s evolution?

Expanding yourself and becoming a brand, getting involved in other businesses … the small part that I’ve played is probably just setting an example for those watching me and those coming after me. And with that said, I got that from watching Jay-Z, Reverend Run and Russ [Simmons] move. How they never stopped and just evolved, [especially] the way Jay has evolved. (Laughs.) I’m trying to follow stuff like that. And hopefully those coming up under me will follow my footsteps.

Do you have a wish list of other business opportunities you’d like to pursue?

Oh, no. I don’t have a list. You limit yourself when you put a list together. (Laughs.) But I can guarantee there has to be a feeling that makes me go forward with any [business] decision that I make. So therefore I know that it is organic.

You underscored your electric stage presence with 2010’s Rebirth, your creative leap into rock after ventures into blending rap with pop and singing. What influence has that had on next-gen artists with similar vibes, like Lil Uzi Vert, Travis Scott, Young Thug and Trippie Redd?

Sometimes people ask me how I feel about everybody looking like me, everybody getting tattoos, etc. That’s like seeing your kid come out of the room and looking just like you; it feels amazing. So the visible influence is kind of obvious because I know for a fact I didn’t get this look from anyone. There was no one that inspired this look. I just ran into looking like this. (Laughs.) But other than that, I hope that my work ethic [is influential as well].

How would you describe your work ethic? You seem like a 24/7 studio guy.

Exactly. So when other artists get around me, you know, they can smell that. It is impossible for them not to. And whenever they leave, they leave with something, as they remember that smell. And hopefully it does something for them.

So is your phone ringing off the hook with people asking you for advice?

No, not advice, not at all. That’s because they don’t have my number. (Laughs.) I have three sons and a beautiful daughter who get the advice.

On Billboard’s recent GOAT list of hip-hop’s top 50 artists, you landed at No. 7, between The Notorious B.I.G. at No. 6 and Drake at No. 8. What did you think of your placement?

That’s awesome. You would be happy to be anywhere on that list.

So which rappers would be in the top five of your own GOAT list?

There’s no specific order, but it’s simple. For me, it’s always been Missy Elliott, Jay-Z, UGK, Goodie Mob and Biggie.

Why those five? What’s the throughline for you in terms of their place in the genre’s evolution?

It’s because I organically grew up on [them]. You know, when you’re asked, “How’d you start listening?,” there’s a story for everybody … like, someone I know told me to start listening or whatever. But like I said, every decision I make is organic.

What does it take to break new hip-hop artists today?

Today, you have to know social media. If you don’t, you have to have a team that does. That said, the main thing today is what it has been yesterday and the day before yesterday: You just have to have real talent. Real, everlasting and undeniable talent. That’s how you still break an artist. Once you find that in an artist, then use and highlight that as much as you can, because it’s hard. There are lots of artists that want to be exactly what they see [and hear] on social media. They just want to be that instead of being what they actually can be. So get them to believe in what they are and what they truly can be. And even if it is a challenge, that challenge has always been one of the most fun things ever for me. I love it.

What exactly do you say or do when working with and developing new artists, since, as you just said, it’s so difficult to rise above everything that’s out there?

That you have to be at least good in whatever genre that you’re attacking, whether it’s hip-hop or not. And then you have to be willing to work as hard as you can to turn that good around into great. So come high at me, and you’ll be talking about the greatest. It’s that plain and simple. There are no keys. You just need to believe in what you’ve got and what you’re attacking, if you believe in it. Show me. Think harder, you know? Challenge yourself.

What’s been your own secret to longevity?

I don’t have a secret. I just work. I just keep going. I never stop. It’s just the work ethic, plain and simple. No more, no less; I don’t do nothing but my music. And also, in my mind, every single time I say the word “work,” I ask God to forgive me. Cuz I know this has never been a job. It’s just a dream come true. So that’s why I’ve never stopped.

Is it difficult for you to say that to someone who’s not there yet?

Not at all. I can’t tell any other artists that. But if you’re my artist, oh hell, yeah. I’ll let them know. You better go do that sh-t again. (Laughs.)

What are your thoughts on the growing ranks of women rappers? Why has it taken so long for this to happen?

My answer would be, honestly, that it just wasn’t as interesting to women, I don’t think, in the way that Nicki [Minaj], Meg [Megan Thee Stallion] and others are. It’s awesome. I don’t think they looked at or viewed it as something that they wanted to do and actually make a living from it. That’s another part of it. They probably didn’t look at this as something that they could make a living out of.

And perhaps the industry has become a bit more open-minded, too?

Oh, yeah. Definitely. We’re here for everything now.

Where is the future of hip-hop headed — any trends that you’re noticing?

Obviously, always up and bigger and better. Also, what I’m seeing now is the art and the ultimate artist being able to do anything. It’s like when you and I were talking about basketball. Back then, we were looking for a Kareem [Abdul-Jabbar]; if you were tall, we wanted you in the paint. Not even knowing how to shoot a three-pointer; we didn’t even want to see that. Now we’ve got these seven-footers coming in, and we need you [to] know how to dribble like Allen Iverson, how to shoot like Steph Curry. You need to know how to defend like GP [Gary Payton]. And that’s the ultimate artist. I believe that that’s where the genre is headed: artists able to do everything — from singing to tapping into different emotions.

What’s your opinion on artificial intelligence and its potential effect on creativity?

Someone asked me about that recently. And they were trying to tell me that AI could make a voice that sounds just like me. But it’s not me, because I’m amazing. I’m like, is this AI thing going to be amazing too? Because I am naturally, organically amazing. I’m one of a kind. So actually, I would love to see that thing try to duplicate this motherf–ker.

In the wake of AI and other emerging technology, have mixtapes lost their relevance?

The terminology or definition has changed, that’s all. Mixtapes can mean an album mix or anything now. But when it comes to Lil Wayne, everybody knows how I approach mixtapes. So my mixtapes won’t ever change.

Any hints as to what fans can expect when you perform Aug. 11 at the hip-hop 50th anniversary concert at Yankee Stadium?

Do not set expectations for me, because I will always exceed them. So just go there with a clear mind, expect the best — and I’ll be better than that.

This story will appear in the Aug. 5, 2023, issue of Billboard.