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.

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.”

He later trimmed down his stage name to just ‘Diddy’, aiming for a closer bond with his fans
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.