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 pick

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