In 2021, writer Tressie McMillan Cottom profiled Sean “Diddy” Combs for Vanity Fair. He was in the middle of his rebrand as “Love”  and spoke to her about his new image. Combs spent the interview bragging about his wealth and appearance, but it rang hollow to Cottom. She said she walked away from the interview thinking that Combs reminded her of a scared child.

Sean ‘Diddy’ Combs did not come across well to one profiler

When Cottom left her interview with Combs, which she conducted at his home, she called her mother. She said that the mogul reminded her of a “child.” He spent much of the interview boasting.

“He kept talking about, ‘I’m an attractive young man,’” Cottom told The Independent. “The way he would describe himself, first of all, was ‘young’ which I thought was bizarre. It was telling that he has created a character version of himself that is powerful and sexy and physically attractive when really, what he is, is rich.”

To her, it felt like Combs had to speak highly of himself to cover up insecurities.

“Absent the money and the star power, I’m not sure we would look at him and think those things, but that’s the kind of story a very scared, self-conscious little boy would write about himself, right?” she said. “The ladies love me. I’m so powerful. I’m so dope. I’m a playboy. That sounded like a child.”

The profiler added that Sean ‘Diddy’ Combs grew uncomfortable at points

During the interview, Combs spoke about how much he admired the Me Too movement.

“When they said in the #MeToo, when it was over, it was over … The #MeToo movement, the truth, is that it inspired me,” he said. “It showed me that you can get maximum change.”

When Cottom asked follow-up questions, though, Combs seemed unable to answer. She felt he had preplanned talking points that weren’t true to his beliefs.

“He couldn’t even perform it well … It was another one of those moments where it was clear that it was out of context, the quotes,” she says. “He wanted it to make the piece, but he didn’t have anything to make it significant. And he did get very uncomfortable when I asked follow-up questions.”

She said the experience was very strange

As Cottom and Combs talked, she became aware that there were many people in the house with them.

“The first floor was set up very deliberately,” she said. “But there was a ton of activity I could hear, people, on the second floor … it sounded like there had to have been about maybe a dozen people upstairs.”

She said his staff were “very deferential” to him. She believed he orchestrated everything for her benefit.

“I do remember thinking, everything that is not being said here is as important as what he is saying – so who is here, where they’re standing, who is silent, the people who kept entering and exiting the room and somehow knew exactly what they were supposed to do … all of that, to me, was as much a part of the story, and it was extremely unique.”

Because of this, the interview has continued to stand out to her.

“And I like to think I’ve talked to some strange characters in my time, but this was in the top tier of strangeness.”