Diddy Brings Same Old Hustle to Host of New Pursuits

DiddyHeidi Gutman/ABC
Diddy sat down with "Nightline" co-anchor Martin Bashir for a lengthy interview touching on the arts of self-promotion and self-preservation, aging, parenthood, acting and more.

It was another day in the life of the mogul variously known as Sean Combs, Puff Daddy, P. Diddy and now just plain Diddy -- a man of many names and plenty of products.

He already has his own clothing and fragrance lines, a restaurant and a lucrative deal with Ciroc premium vodka. He's talked about opening a business school. And that's not even to mention the main attraction -- the music.

Diddy: The Modern MogulPlay
Diddy: The Modern Mogul

Amid a promotional orgy for the Diddy product du jour, a new line of headphones, the hip-hop star greeted me with enthusiasm.

"Whas up, how you doing man!" he said. "I'm such a fan of yours, I got a little bit nervous when I found out you were interviewing me."

In a lengthy interview on an oppressively humid day in his hometown, New York City, Diddy expounded on the arts of self-promotion and self-preservation, aging, parenthood, acting and more.

"I have the knack, whether it's the fragrance, the clothing line or headphones -- I'm just trying to create stuff that fits our lifestyle, so people understand how we walk, talk and think," said Diddy.

VIDEO: Entertainment mogul tells Martin Bashir which team hes placing bets on. Play

The star keeps up a punishing schedule.

"I was proud of working 18 hours a day and sleeping three hours a night," he said. "It's something now that has turned into a problem for me: not being able to sleep ... having insomnia. ... I take sleeping pills -- I don't like to take them on regular basis -- or different teas and lavender. I try everything, you know. ... My mind is always racing, and always going and always working, and it's a gift and a curse. When I was starting out it was something I embraced, but now it's something that I hate, it tortures -- it will torture you."

VIDEO: Diddy takes "Nightline" on shoot for new album, "Last Train To Paris."Play

A Vast Collection of Brands

Diddy's gift has been to produce a vast array of branded products. The 40-year-old mogul wants to dress you in his clothes, spray you with his fragrance, then pound you with his music.

"I was going to make the fragrance you put on, the clothes you wear to work," he said. "I was going to have the television shows you watched, before you went out to the club, to listen to the music I produced, to buy the vodka that I promote."

Some people might call all that a form of megalomania?

"It could be," Diddy conceded.

Diddy calls himself the black James Bond. Neither shaken nor stirred -- but always selling.

Diddy: 'Curator of Cool'

I asked Diddy if there was anything he wouldn't promote. Diddy dog food?

"How about Diddy dog food: Make your dog yap to a rap," he riffed. "You know, I would do what's organic for me. I would do candles. I love candles. I would do jewelry that fits. I would do hotels. Whatever was in the realm of entertainment or lifestyle, or curator of cool, that's what I do."

Diddy says the foundation of his entire Bad Boy business empire -- the umbrella organization that made $345 million last year -- is the music he produced during the '90s.

"I take pride in being one of the most successful producers in hip-hop history, having the most successful record in hip-hop history, I have the most number ones," he said. "A a hip-hop artist, these are things that I say that people are like, 'You have the most number ones?' Yeah, I'm the rap artist with the most number-one singles, that's the most in history from a hip-hop artist."

Unlike many hip-hop artists, nurtured in poverty, Sean Combs was born in November 1969 into an aspirational family. His mother, a schoolteacher who often took second jobs, moved the family from the city to Mount Vernon, N.Y., when Sean was 12 so he could attend a well-regarded boys' school.

"My mother was always working for a job, so I guess I was always trained that I should have multiple jobs, multiple aspirations," Diddy said. "And I remember she had multiple aspirations, always hearing about her dreams and things she did in the past and things she wanted to do."

Breaking Into Music

At school, Diddy earned the nickname Puffy because he'd puff out his chest on the football field.

He enrolled at Howard University in Washington but dropped out to take an internship at New York's Uptown Records. Within a year, he became vice president.

By attracting artists such as Mary J. Blige and The Notorious B.I.G., a.k.a. Biggie Smalls, Diddy became the East Coast's super producer. But it was also during the mid-'90s when a venomous feud broke out between his label and the West Coast's Death Row Records.

In September 1996, Tupac Shakur -- the most talented artist at Death Row -- was murdered in a drive-by shooting in Las Vegas. Six months later, Biggie Smalls suffered a similar fate in Los Angeles. And although the killings are still on the minds of many, Diddy is reluctant to discuss either one.

"I just decided it wasn't something that I was going to be talking about no more, you know," said Diddy. "It's in the past. I've talked about [Biggie Smalls] so much. I love him. I miss him. It's a tragic loss."

I asked whether Diddy had any idea of who killed Biggie.

"No. ... No idea," he said.

And Tupac?


He said he still feels the loss -- and not just of his friends.

"Of course, I feel the loss of my friends," he said. "I feel the loss of Tupac ... and I feel the loss of African-Americans. ... Not just African-Americans, but anyone who has died with guns."

Diddy: Mainstream Star

Since the feuds of the '90s, Diddy has left the conflicts of the rap world behind and become a mainstream star. Much like Simon Cowell, he has used his music credentials to launch numerous reality shows, including "Diddy Starmaker," "I Wanna Work for Diddy" and "Making the Band."

But Diddy's demanding demeanor in some of the shows has been mercilessly ridiculed by many, including comedic star Dave Chappelle.

I asked him about his response to individuals within the hip-hop community who say he's not a hard-core rapper fighting injustice and racism, but a brand that's basically available to the highest bidder.

"My record basically speaks for itself," he replied. "I produced some of the hardest, most street-credible albums in history of hip-hop. I produced the greatest rapper of all time."

But wasn't that a while ago, now?

"Yeah, I mean, you can't erase it, it's up there, you can't just take down the records once they are set," Diddy said. "You gotta come break 'em. So I invite any of my fellow competitors to step it up, you know, stop sleeping, join the game, baby!"

The New Album

As if to emphasize the point, Diddy is about to release his first album in two years, "Last Train to Paris," featuring his latest ensemble, Dirty Money.

I asked him about a line from the album: "I started this s***, motherf******. Y'all just rented it while I was gone." What did he mean by that?

"It's just hip-hop is a very competitive art form, and when you come back, you got to come back strong, you have to let them know who's the daddy of this situation," Diddy said. "You need to remind everybody, the competition and fans, who was the originator of the style, the swag, and the flavor is -- a lot of it comes from me, a lot of the things that I've done. I can't erase the things I've done. I'm not trying to brag. But I'm trying to make sure we don't forget the things I've done and who did them first.

Diddy: Facing Down Middle Age

Even as he enters his fifth decade, Diddy is still driven by a ferocious desire to keep selling his brand, producing products that will appeal to his global fan club.

How does a hard-core rapper, hip-hop producer, enter middle age?

"Hopefully, you enter it gracefully, and really turning back the hands of time," he said. "Your spirit can always stay youthful. No one can take away your spirit. But I think you have to use your experiences to your advantage. I don't talk about the same things that I talked about. This album's about love.

But the pathway of love has not been entirely straightforward for a man who, apart from Presidents Barack Obama and Nelson Mandela, could be the most famous black man on the planet.

Diddy has six children by three different mothers.

"I definitely enjoy the responsibilities of fatherhood," he said. "It's one of my proudest achievements. It's probably one of the things I can honestly say I'm not the most successful at...

"I think that my kids deserve more personal time from me," he said. "It's just, it gets hard when you're trying to make sure you're providing for their future, and having to work, and also being a workaholic, and then also the time that your kids deserve as far as raising them. So I think I do a good job at raising my kids."

Diddy on Marriage

What about marriage?

"Marriage for me is something that I see differently than a lot of people," he said. "Based on what I see out here, I don't see it as a commitment. I don't know a lot of people that are married are happ. Ninety percent of the people that I speak to that are married are miserable. Ninety percent of the men I know that are married, they are not really as committed. ... And also my background, I never grew up seeing that. ... My mother never had a man around us. My father was killed when I was 3. So just based on the way what I was accustomed to, I wasn't well-versed in that."

I asked Diddy about what Barack Obama, then a senator, said on Father's Day almost two years ago, about how children who grow up without a father are nine times more likely to drop out of school and 20 times more likely to end up in prison.

Might Diddy be setting a bad example, by being a man with multiple children who have multiple mothers?

"I think it depends on how you look at it," Diddy said. "All of my kids are well taken care of. They all go to the best schools. ... All of the mothers are taken care of financially, and I'm there for my children as a father.

It's true that Diddy takes care of his family financially. For his 16th birthday, he bought his son Justin a Maybach car worth almost $400,000. Was that appropriate?

"I think its appropriate to give my kids whatever I want to give my kids," he said. "I feel the way I raise my children, I don't have to explain to you or anyone else, 'cause nobody knows the way I raise my children. So nobody knows the lessons that I've taught my children to understand, if they are mentally ready for that."

Does he think giving a teenager such an expensive car was a valuable lesson about money?

"It wasn't even about a lesson; it's what I wanted to do," he said. "I could do whatever I want to do and you can't question me about it."

Diddy: 'Get Him to the Greek'

Diddy currently is starring in the movie "Get Him to the Greek," he's cast as a hyper-controlling, expletive-spewing music executive.

It's his biggest movie role to date, and he concedes that it draws heavily upon his own experience.

"I think that what I did, I use a piece of myself in the movie -- the exaggerated piece that people think about me -- and exaggerated it even more to make people laugh," he said. "I mean, I laugh at myself all the time, and I laugh at what people think that I am, really am like. They don't really know me, and just the perception or the image that has been created is really far from who the actual person Sean is. But the image of P. Diddy and Puff Daddy is in the movie, and some of that makes you laugh.

"A lot of directors haven't wanted to hire me because they think that I'm famous ... but I've always just tried to promote out to Hollywood that I'm the perfect combination of art and commerce," he said. "I could deliver the art on the acting role, and I can deliver the seats in the theaters, so I look to that to be my future."

It is where Diddy sees his future: mesmerizing audiences, not with his music, but with his acting.

And with that it was time to say goodbye. Diddy was off to promote his movie, his new album, his vodka and, of course, his headphones. They're called DiddyBeats, and he says they're the best that money can buy. And who are we to argue?