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It was 20 years ago this week (Nov. 29) that 16-year-old Chris Brown vaulted onto the scene with his self-titled debut studio album and triple platinum-certified Hot 100 No. 1 “Run It!” And in celebrating that anniversary, Brown — under the guidance of manager Anthony “Ant” Wilson of Tycoon Music — has achieved various other career milestones during what’s become an even more momentous year for the singer-songwriter.

Brown kicked off 2025 with the best R&B album Grammy for his latest album 11:11 (Deluxe) — his second win in that category after 13 years. He’s now closing out the year with two more nominations for the 2026 Grammy ceremony: best R&B song and best R&B performance for “It Depends” featuring Bryson Tiller, which peaked at No. 16 on the Hot 100. Prior to that in 2024, Brown picked up his first RIAA Diamond-certified single for “No Guidance” featuring Drake.

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Of witnessing Brown’s second Grammy win, Wilson — a 2025 R&B/Hip-Hop Power Players honoree — told Billboard in August, “Winning isn’t everything, but it feels good. And the consistent recognition of his artistry continues to solidify him as one of the biggest artists in the world.”

Between those Grammy bookends, Brown embarked on what’s since been logged by Billboard Boxscore as his highest-grossing live outing to date, the Breezy Bowl XX World Tour. Spanning 39 cities and 48 shows, his 20th anniversary and first-ever stadium run (June 8-Oct. 16) earned $300 million and drew 2 million fans across North America, Europe and the U.K. Accompanied by Tiller as a special guest through the run and Grammy-nominated artists Jhené Aiko and Summer Walker on select dates, Brown also welcomed pop-up performances along the way by Usher, 50 Cent, GloRilla, Tyga, Bow Wow, Sexyy Red and Davido during his three-hour, 56-song set.

It’s Brown’s indefatigable energy and love of performing that Wilson first focused on strategically when he became the global star’s manager 10 years ago after predecessors Tina Davis and Mike G.

“We started off doing club and spot dates,” Wilson recalls. “Then we got the Heartbreak on a Full Moon tour [2018 with H.E.R., 6lac, and Rich the Kid]. I just wanted to get him back to the touring part of the business because I felt he could touch the most fans there. That was my initial goal.”

Wilson also created the annual Tycoon Music Festival. Presented this year in association with Live Nation and 313 Presents, the festival marked its sixth anniversary on April 19 at Little Caesars Arena in Detroit. Headlined by Brown, the lineup also starred Skilla Baby, Fabolous, Gucci Mane and Wiz Khalifa with surprise appearances from Sexyy Red, G-Herbo, Payroll Giovanni and Tee Grizzley.

Based in Las Vegas, as is Brown, Wilson recently spoke with Billboard about what’s next on the drawing board for him and his superstar client.

Chris Brown and Anthony “Ant” Wilson

Travis Colbert

What’s it like managing such a tireless artist as Brown?

We don’t sleep too much over here [laughs]. That’s because he stays up working in the studio he has in his house. He’s in that studio every day until we put out an album. And then the hard part before that is figuring out what songs are going to make the album. Chris also has a billion ideas about different things. So another hard thing is trying to get those billion ideas down to at least 10.

Talk about the rapport between the two of you, which is an important part of the artist/manager collaboration.

I met Chris when I was working with Bow Wow. that’s when Tina was involved. She’s a friend of mine as well. So I used to help out whenever she needed some assistance. Mike G was there too; we were all together then. But Chris is my brother first then it’s business, I don’t hope that he wins. He has to win because he’s my family. So that’s why there is no sleeping because I’ve got to make sure he does. I don’t know if there’s a blueprint on how to manage an artist. Every artist is different. But there is one key thing: understanding the artist and the fans of that artist.

Very few artists have made the successful transition from teen to adult star. Why has Brown been able to cross that bridge?

A lot of artists can do one thing; they can either sing or they can dance. But not a lot of artists can perform the way that he does: he’s singing, he’s dancing, he’s crying, he’s laughing, he’s flying, He’s doing everything he can to please fans. He’ll take less money just for the production to be what it is. He just wants [his performance] to stand out. Breezy XX was originally three and a half hours. I’m like, “Chris, come on. We’re going to run into overtime on every show. Like I said before, that’s the hardest thing … trying to get things down to where we’re both happy [laughs].

A new album coming before this year is out has been rumored given the 20th anniversary. Any hints about the next project?

There’s always an album. The name of it always changes. The songs always change. Even with the last album, we were in the studio putting another song together on the day before it came out. So I can’t say the name or a date for the album. I’ll leave it open because he could wake up and say let’s put it out next week. I’m ready though. I have it [the album] at the moment, but it changes every week.

Chris Brown performs in San Diego, CA, on September 18, 2025.

Acre Media

What else is next? A concert movie à la Taylor Swift and Beyoncé or a return to acting?

He loves and wants to act. There are acting classes, and he’s gearing up for that. I also think the Super Bowl would be a great place for him. I believe it will happen.

Have there been any overtures on that front?

We’ll just see.

How has it been navigating the negativity that he still encounters as you work to move his career forward?

It’s nothing that I’m not used to at this point. We just smile and keep going. I just try to show improvement with work over the words, you know? I think that’s the best way. But his kids ground him. He’s a great, involved dad. I also think Chris’ fans love him so much because they can relate. He’s a real person who’s gone through things that others have but he did it in front of the world. So I feel like that’s his legacy: going through life with everyone else.

Now that Verzuz is back, is the long-rumored Usher/Chris Brown match-up a stronger possibility?

It may. Usher and Swizz Beatz are friends of mine; Swizz recently spoke to me about it. I’m not saying no if it makes sense.

Beyond your ownership of the Tycoon Festival, what other projects are you shepherding?

I also work with 50 Cent in a company called the Green Light Gang. We have 40 TV shows [in the works] at the moment and a few movies. We’re also going to build a production company in Shreveport, Louisiana. So that’s my new baby, television.