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Justin Timberlake is set to explore some of the most controversial moments of his career in a new four-part documentary series for Apple TV, which is expected to premiere in December. The series will reportedly feature Janet Jackson, raising speculation that it will address their infamous 2004 Super Bowl halftime performance, which was marred by a wardrobe malfunction. This project comes five years after Timberlake publicly apologized to Jackson for his role in the fallout from the incident, acknowledging the impact of misogyny and racism on their careers. Additionally, Timberlake has faced personal challenges, including a DUI arrest in 2024 and a diagnosis of Lyme disease, which he has described as debilitating. Details about the documentary remain limited, with no further comments from Timberlake’s representatives or Apple TV.