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Chris Brown Celebrates 20th Career Anniversary with Grammy Wins and Record-Breaking Tour

This week marks the 20th anniversary of Chris Brown’s emergence as a musical force with his self-titled debut album, which featured the chart-topping hit “Run It!” Since then, the singer-songwriter has continued to garner acclaim, recently celebrating a series of significant career milestones. Under the management of Anthony “Ant” Wilson at Tycoon Music, Brown has had an eventful year, reflecting both growth and versatility as an artist.

Kicking off the year on a high note, Brown earned the Grammy for Best R&B Album for his latest work, “11:11 (Deluxe).” This marked his second Grammy win in the category after a 13-year hiatus. As the year closes, he has received two more nominations for the upcoming 2026 Grammy Awards—Best R&B Song and Best R&B Performance for “It Depends,” which features Bryson Tiller and reached No. 16 on the Hot 100. Additionally, in 2024, Brown achieved his first RIAA Diamond certification for the single “No Guidance,” a collaboration with Drake.

Reflecting on Brown’s achievements, Wilson, who has been instrumental in shaping his career over a decade, noted the importance of continued artistic recognition, stating, “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.”

This impressive year has also included the Breezy Bowl XX World Tour, which has been recognized by Billboard Boxscore as Brown’s highest-grossing live tour to date. Spanning 39 cities and 48 shows, the tour celebrated Brown’s 20 years in the industry, earning a staggering $300 million while attracting 2 million fans across North America, Europe, and the U.K. The tour featured appearances by prominent artists such as Tiller, Jhené Aiko, and Summer Walker, alongside surprise performances from Usher, 50 Cent, and more.

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Wilson shared insights on managing Brown, highlighting his unwavering dedication to music. He noted, “We don’t sleep too much over here. That’s because he stays up working in the studio… Chris has a billion ideas about different things.” The synergy between Brown and Wilson has been pivotal, with Wilson considering their relationship to be rooted in brotherhood.

Many artists find it challenging to evolve from teen sensations to enduring adult stars, but Brown has managed this transition successfully thanks to his multifaceted talent. Wilson explained, “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.” This commitment to performance has set Brown apart in an ever-evolving industry.

Looking ahead, rumors swirl about a new album possibly dropping before year-end, although specific details remain under wraps. Wilson teased that the project is constantly adapting, stating, “The songs always change… he could wake up and say let’s put it out next week.”

Beyond music, Brown has expressed interest in returning to acting, with Wilson indicating that the artist is preparing for this next chapter. Discussions about Brown performing at high-profile events like the Super Bowl also remain on the table, generating excitement for potential future appearances.

Navigating the complexities of public perception continues to be a challenge, but Wilson emphasized the importance of positive progression over negativity. “It’s nothing that I’m not used to at this point. We just smile and keep going,” he said. Brown’s role as an involved father adds depth to his public persona and serves as a grounding influence amidst the scrutiny.

As the entertainment landscape evolves, there are hints at a possible Verzuz match-up with Usher, as discussions have begun to surface. With Wilson’s expansive management portfolio—including collaborations in television production—the future holds great promise for both Brown and those who work alongside him.

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