The personal Oprah question Diddy refused to answer
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The personal Oprah question Diddy refused to answer

Bad Boy Entertainment founder Diddy is one of the wealthiest figures in hip-hop and has become a mogul since he founded his label in 1993. Diddy (real name Sean Combs) signed and invested in Biggie Smalls, making millions from his success.

Bad Boy Entertainment was set up so that Diddy, who had his ear to the streets of the East Coast, could draft in the best new talent hip hop had to offer. As a businessman, he packaged and marketed all of his artists with ingenuity. With the knowledge he acquired at Uptown Records, he knew what MCs needed to cross into the mainstream, and everything he touched turned to gold from thereon.

Ever since he appeared on the scene, Diddy continued to grow, and in 2005 he got listed in Time Magazine‘s 100 Most Influential People’ list. With his music and film credits beginning to accrue and with his network within the film and music industry growing, Time Magazine knew that Diddy was becoming powerful. The following year, he released his fourth album, Press Play.

Following the release of Press Play, Diddy sat down for an in-depth interview with the billionaire television host and journalist Oprah Winfrey for her magazine O. The discussion saw Combs talk about a range of things from his time at Uptown Records to his relationship with Biggie Smalls. However, there was one question he simply wouldn’t answer.

While discussing his name change to P Diddy, Oprah asked how he initially got the name Puff Daddy. In response, Combs unveiled, “It’s a nickname somebody gave me.” However, when asked what it means, he told Winfrey, “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.”

Winfrey comically asked if it was because he looked “puffed up,” to which he responded, “It’s just a silly name.” However, Oprah quickly realised her line of questioning was not going anywhere and stated, “I can see that you’re not going to tell me.” Laughing, Diddy assured Winfrey, “I’ll answer every other question.”

In 2001, Combs changed his name from Puff Daddy to P Diddy, and in 2009, he changed it to Diddy after the name of his group Diddy Dirty Money. You can hear Combs speaking about his name with Jimmy Kimmel in the video below.