Justin Timberlake is reportedly getting ready to revisit some of the most talked-about chapters of his career in a new four-part documentary series expected to arrive on Apple TV in December.
According to Variety, the project will feature Janet Jackson discussing their controversial 2004 Super Bowl halftime performance, an incident that became one of the biggest scandals in television and pop music history.
The series, directed by filmmaker Fisher Stevens, is also expected to address Timberlake’s past relationship with Britney Spears. Sources indicate that the singer will respond to some of his former girlfriend’s recent public comments, potentially bringing renewed attention to a relationship that has remained a subject of discussion for more than two decades.
Jackson’s reported involvement is particularly noteworthy. During their performance at Super Bowl XXXVIII, Timberlake pulled away part of Jackson’s costume, briefly exposing her breast to millions of television viewers. The incident triggered widespread criticism and intense media coverage, with Jackson facing significant professional consequences.
The controversy also raised lasting questions about how the entertainment industry treats male and female performers differently. While Jackson experienced substantial backlash, Timberlake continued building his successful solo career.
In 2021, Timberlake publicly apologized to both Jackson and Spears, acknowledging his role in situations that had negatively affected the two women. The upcoming documentary could provide an opportunity for additional discussion about those events, although the extent of the conversations remains unknown.
The project arrives during a relatively quiet period in Timberlake’s career. His most recent studio album, *Everything I Thought It Was*, was released in March 2024, followed by his extensive Forget Tomorrow World Tour.
That tour concluded in July 2025, when Timberlake revealed that he had been diagnosed with Lyme disease. He explained that the illness had contributed to physical difficulties during some performances, including fatigue and nerve-related symptoms.
His recent years have also included legal troubles stemming from a June 2024 traffic stop in Sag Harbor, New York, which resulted in a conviction for impaired driving.
Despite those challenges, Timberlake has continued making occasional musical appearances, including a guest performance with Jay-Z in Paris.
The documentary will mark another collaboration between Timberlake and Apple, following his starring role in the 2021 Apple Original film *Palmer*.
For now, many questions remain unanswered. Apple has not announced an official premiere date, and representatives for the individuals involved have not publicly confirmed the reported details.
If the series arrives as reported, it could offer audiences a closer examination of Timberlake’s career, his relationships with two of pop music’s most recognizable women, and the controversies that continue to shape public perceptions of his legacy.
