Sean “Diddy” Combs has been charged with racketeering conspiracy, transportation to engage in prostitution and sex trafficking, and his trial is currently ongoing in New York City. Model and singer Cassie recently testified about her abusive relationship with Diddy and her struggles with PTSD after it ended.
If you want to understand more about Diddy’s rise and fall, Watch With Us recommends these three docuseries and documentaries currently streaming on Peacock, Tubi and HBO Max.
‘The Fall of Diddy’ (2025)
This five-part docuseries has earned the most positive reception among the Diddy documentaries that are out there. The series features interviews with former associates, such as former assistant Phil Pines, who alleges being coerced into facilitating illicit activities.
It’s an investigative exposé that aims to uncover secrets about the mogul’s life and alleged crimes. The Fall of Diddy is an in-depth docuseries that provides helpful background for those following the trial.
Watch The Fall of Diddy on Max.
Diddy Sues NBC for $100 Million Over Peacock Doc ‘The Making of a Bad Boy’
‘TMZ Presents: The Downfall of Diddy’ (2024-2025)
TMZ is known for its more tabloid-oriented style, and that tone is definitely apparent in their four-part docuseries. After the original TV special, The Downfall of Diddy, aired last April, TMZ released three more installments: The Indictment, Inside The Freak-Offs and His Defense. All four are worth watching if you want a salacious take on an already controversial story, but the first special is the best one to watch for people who don’t know too much about Diddy.
Watch TMZ Presents: The Downfall of Diddy on Tubi.
Diddy Insiders Speak Out in Trailer for New Peacock Documentary
‘Diddy: The Making of a Bad Boy’ (2025)
This Peacock original documentary explores more about Diddy’s origin story, digging up information about his parents and his childhood to try to connect the dots to his future behavior. The film includes interviews with former associates and explores Diddy’s personal and professional life.
Watch Diddy: The Making of a Bad Boy on Peacock.
