Chelsea Handler Praises Ex-Boyfriend 50 Cent for Diddy Documentary

Chelsea Handler harbors no animosity towards her former boyfriend Curtis “50 Cent” Jackson — and is even offering him high praise.

The 50-year-old comedian was prompted to name her “celebrity of the year” during a recent appearance on the “LadyGang” podcast and she swiftly mentioned the rapper and his Netflix documentary concerning Sean “Diddy” Combs.

“I want to remain loyal to him as a past romantic partner,” Handler stated during the Tuesday, December 23, podcast episode. “He released that Diddy documentary. He’s been criticizing Diddy throughout this entire situation.”

50 Cent produced Sean Combs: The Reckoning, which premiered on Netflix earlier this month. The four-part series featured previously unseen footage of Diddy alongside interviews with several of his former associates.

50 Cent's Diddy Doc to Include Unseen Pre-Arrest Footage, Juror Interviews

Diddy was apprehended in September 2024 and charged with sex trafficking, racketeering and transporting individuals for prostitution. He entered a plea of not guilty and was acquitted of the sex trafficking and racketeering charges this past July.

The disgraced music mogul was found guilty of two counts of transportation to engage in prostitution. He is currently serving a 50-month sentence at New Jersey’s FCI Fort Dix.

“I think I attended one party at Diddy’s perhaps, like, 20 years ago,” Handler said during her “LadyGang” podcast appearance. “But I recognized it immediately. I thought, ‘This man is so unpleasant.’”

Handler said that she and 50 Cent never discussed his issues with Diddy during their relationship in 2011.

“I admire what he’s been accomplishing, and I appreciate that he covered the legal expenses for those women,” she continued. “I’m going with 50 Cent, simply because he deserves an award every year.”

She added, “I simply enjoy discussing him, because he’s such a kind person. You know what, it’s wonderful to have ex-boyfriends that you don’t find repulsive.”

Diddy’s representatives strongly condemned 50 Cent’s docuseries, labeling it a “shameful smear campaign” in a statement to Us Weekly earlier this month.

50 Cent's Netflix Docuseries About Diddy’s Alleged Crimes Spans 'Decades'

A spokesperson for Diddy claimed that “Netflix utilized stolen footage that was never approved for distribution” for the docuseries.

“As Netflix and CEO Ted Sarandos are aware, Mr. Combs has been compiling footage since he was 19 to share his own narrative, in his own way. It is fundamentally unfair, and unlawful, for Netflix to misappropriate that work,” the statement continued. “Netflix is plainly desperate to sensationalize every aspect of Mr. Combs’s life, without regard for truth, in order to capitalize on a never-ending media frenzy.”

They continued, “If Netflix cared about truth or about Mr. Combs’s legal rights, it would not be extracting private footage out of context – including conversations with his lawyers that were never intended for public viewing. No rights in that material were ever transferred to Netflix or any third party.”

Netflix defended the release of Sean Combs: The Reckoning in a statement of their own, refuting the “false” allegations made by Diddy’s team.

“The footage of Combs leading up to his indictment and arrest was legally obtained,” the streaming service said in a statement to Us. “This is not a smear campaign or an act of vengeance. Curtis Jackson [50 Cent] is an executive producer but does not have creative control. No one was compensated to participate.”