Oprah Winfrey’s testimonies about Diddy make him lose it.

Diddy’s awkward response to infamous Puff Daddy nickname in unearthed Oprah chat

Sean “Diddy” Combs had a candid conversation with Oprah Winfrey back in 2006, where he opened up about his life, but awkwardly refused to reveal the origin of one of his most famous nicknames.

Oprah pictured with Diddy
Numerous videos have since resurfaced, casting past events in a new light. (Image: (Image: Getty))

During an intimate discussion with Oprah, peeling away the layers of his complex life, Diddy evoked curiosity by avoiding details about the origin of his well-known moniker ‘Puff Daddy’. The conversation, part of an interview for Oprah’s O magazine, began casually as Oprah inquired about the name’s beginnings.

“It’s a nickname somebody gave me,” Diddy replied, and when probed further about its meaning, he became notably reserved: “I’ve never told anyone that. I know you get people to tell you everything, Oprah. But I can’t look you in the eye and explain that one,” Diddy confessed.

Oprah, sensing his hesitance over whether ‘Puff’ signified something else, got the brush-off with Diddy’s comment, “It’s just a silly name.”

Diddy and Oprah

He later trimmed down his stage name to just ‘Diddy’, aiming for a closer bond with his fans (Image: (Image: Getty))
She acknowledged his reticence, observing, “I can see that you’re not going to tell me,” to which Diddy countered: “I’ll answer every other question.”

The enigma around ‘Puff Daddy’ intensified after legal troubles in 1999 involving allegations of possessing a weapon and bribery related to a nightclub shooting in NYC. Despite avoiding conviction, these allegations prompted him to alter his image.

“No more Puff Daddy – the first week in June we’re gonna have a name change ceremony,” he announced to MTV News back in 2001. “I’m rockin’ with ‘P. Diddy’ now. My man Biggie gave me that name.”

He later trimmed down his stage name to just ‘Diddy’, aiming for a closer bond with his fans. The artist has since chosen a new alias, opting for the handle ‘Love’.

The once-celebrated music mogul is currently being held at Metropolitan Detention Center in Brooklyn, following a denied $50 million bail proposal due to flight risk concerns and possible danger to the public. Despite facing charges, he maintains his innocence along with his legal team.