Cigar Aficionado

In his day, singer James Brown was known as the hardest-working man in show business. He never had to compete for the title with Sean Combs.

Even his name keeps him busy: In the course of a career that started in 1990, Combs has been known as Puff Daddy, Puffy, P. Diddy and just plain Diddy. Listening to Combs talk about his various businesses, it seems plausible that those names reference a small army of clones he uses to keep the numerous branches of the Combs empire operating smoothly.

He has a record company and a TV network, works in the recording studio producing for other artists as well as making records of his own, heads up the Sean John clothing and fragrance lines, is involved with two premium liquor brands and more.

Sitting in his dressing room at a photo studio space near Los Angeles' MacArthur Park, Combs is pondering a question about time management when he is interrupted by a text. "Sorry, it's my girlfriend," he says, tapping out a quick message. First things first.

He is 46, but with his shades off, his smile is surprisingly boyish. He has the build of a former athlete, not massive like a linebacker, but solid and fleet looking like a defensive back, a position he played with aplomb at Mount St. Michael Academy in the Bronx. More recently, he showed his athletic prowess by running the New York City Marathon in a respectable four hours and 15 minutes.

He sits atop an empire that seems to expand annually, with a family that includes six children from three women. For all he has done, Combs has many things he still wants to do and not enough time in which to do them.

"I definitely wish there were more hours in the day," he says.

Even at a photo shoot, Combs is the hub of a surprisingly vast collection of enterprises that constantly pull at him. While he changes clothes between setups, he's also talking to his manager about upcoming and ongoing projects. The phone in his pocket may be on silent mode but you can practically feel the energy emanating from it, as it's bombarded by texts and e-mails.

Forbes magazine estimated Combs' net worth at $735 million last year, putting him at the top of its list of the world's richest hip-hop artists. When stacked up against all musicians in 2015, he was the eighth-highest-paid, at $60 million, and he was the only one who did it without the benefit of a tour.

But there is far more to his ventures than music alone. Combs Enterprises comprises a number of divisions, including a talent and marketing agency, his affiliations with Cîroc Vodka and DeLeón Tequila, REVOLT TV, Bad Boy Records, and Sean John fashions and fragrance. Most recently, he, Ron Burkle and Mark Wahlberg jointly acquired Aqua Hydrate, an alkaline-rich performance water (and pledged a donation of a million bottles for the water-needy citizens of Flint, Michigan.) How does he decide what fits the Sean Combs template?

"If it's not authentic or in my wheelhouse, I shy away from it," Combs explains. "Everything is part of creating this dream, creating this world: that, when you get up in the club to dance, you're dancing to a record from my label, you have on a Sean John suit, you're wearing Sean John cologne—and you're drinking Cîroc. Or it's after work and you kick back and watch REVOLT, and you're drinking DeLeón.

"It's the dream of creating a world, creating a lifestyle for this generation's culture, which a lot of people underestimate."

"He's built his brand as a discerning arbiter of style," says Dia Simms, president of Combs Wine & Spirits, a division of Combs Enterprises. "He's not espousing any product he doesn't believe in. There's an incredible responsibility when people listen to you like that. There's a quote [by the late Gen. Omar Bradley] that reminds me of him: ‘We need to learn to set our course by the stars, and not by the light of every passing ship.' There's not a business school that can teach you to do what he does."

What he does is get behind products and projects with a passion and an understanding that achieve results. One of those products is the high-end vodka, Cîroc. When Combs partnered with the brand's parent company, Diageo, to raise awareness and lend his face to the advertising, sales skyrocketed.

"When he got involved with Cîroc, they were working on getting the brand to sell 400,000 cases a year," says Simms. "Sean met with the distributors and said, ‘I'm going to sell a million cases.' And then they sold two million."

Today, Combs's success has put him in the enviable position of not having to worry about having more coming in.

"I can make money," Combs says. "But I can't make time. It's Friday today—but it feels like it was just Friday night yesterday. When I think about time, it's important for me to be as present as possible. That's a journey I started going on when I realized that time was ticking. You get to halftime in your life and realize that it's important to live in the present because life is short."

Born in Harlem, Combs was reared in Mount Vernon, New York, by a single mother who moved there when Sean was 12. His father died when he was only two years old. Though his mother told young Sean that his father had died in a car accident, Combs later uncovered a newspaper clipping about his father's funeral, which revealed that the elder Combs was actually a drug dealer who'd been murdered in a gangland hit.

Growing up without a father, Combs says, helped shape his approach to being a parent.

"I have such a deep appreciation at being able to be a father," he says. "My father didn't get the chance to be there for me. That makes me appreciate the opportunity that much more deeply. I stress the importance of that to my kids—that you can't take having a family for granted."

Religion played a big role in his upbringing. "I was an altar boy," he says. "I was baptized as both a Catholic and a Baptist. When I was growing up, we had a whole day of church on Sunday. So yeah, I was brought up in the faith." Those lessons remain, and prayer is part of his daily ritual. "But I'm not a religious person," he says. "I consider myself a spiritual person. I see a division between being religious and being spiritual."

The women who raised him also instilled him with a powerful work ethic. His mother worked three jobs and his grandmother worked two. Combs earned as well, running several paper routes while attending parochial school.

From an early age, Combs was caught up in popular music, particularly by the emerging rap and hip-hop culture: "I remember the first time I heard hip-hop: Frankie Crocker, this disc jockey on WBLS in New York, played ‘Rapper's Delight' by the Sugar Hill Gang for three hours straight—and it shook the world."

Initially an urban musical form, hip-hop became a phenomenon, muscling its way into popular culture 30 years ago, eventually becoming part of the mainstream. If you don't believe it, look at who's starring in major studio movies: former rappers like Ice Cube, Will Smith, Queen Latifah and Combs himself, who has acted in several films and who starred on Broadway in a well-received revival of Lorraine Hansberry's A Raisin in the Sun.

Turn on the TV and it's the same story: LL Cool J on "NCIS: Los Angeles," Ice-T on "Law & Order: Special Victims Unit." Jay-Z hobnobs with President Obama, who has quoted the rapper's lyrics. So does Combs, who interviewed Barack Obama, then a candidate for the U.S. Senate, at the Democratic National Convention in 2004 for MTV and told him on the air, "You should run for president."

But it took society more than a decade to recognize hip-hop as the art form and, eventually, the influence it has become.

"For a long time, people understood hip-hop as being something gangsta, something black, something street," Combs says. "But it's the only form of music that can mesh with every other form of music. I think people underestimate the kids who listen to it. It is a generational thing and what kids like is the fact that it's so honest. The greatest songs are the most honest, the most genuine. And because it was so honest, so raw, so naked, it took over the masses. You had to be that honest on the records. Plus, hip-hop gives you the opportunity to put more words and feeling into a song than any other genre.

"Nobody could have predicted how big hip-hop would be. I don't think people understand how big it can get. It's not just a lifestyle but a culture—and it's generational."

Combs' entry into the music business dates back to his days as a college student, when he applied to be an intern at Uptown Records.

"Heavy D introduced him to me at Uptown," recalls Andre Harrell, formerly of Uptown and now vice chairman of Combs' REVOLT network. "Heavy never recommended anyone, so for him to recommend Sean meant a lot. Sean was dressed in a white shirt and tie, with this Kid 'n Play high-top fade haircut. And he was very polite. He said, ‘I've researched your company and I think I'm best-suited to work here for you.' So I gave him an opportunity as a summer intern. In the fall, he had to go back to school at Howard University, but he still came up to work in the office twice a week, working for the A&R person. When the A&R person left for Columbia Records, Puffy took me to lunch to talk—and asked for the job. As it turned out, the guy who was leaving had already recommended that I hire him. He was pretty happy to hear that; he was 19 or 20."

After three years with Uptown Records, he left to start his own label, Bad Boy Records, taking his good friend, rapper Notorious B.I.G., with him. He had almost instant success with the late rapper, as well as Craig Mack, singer Faith Evans and rappers like Mase and The Lox. Combs created a production team that worked with a variety of artists: Mary J. Blige, Usher, TLC, Mariah Carey and Aretha Franklin, among others.

"He loved the culture," Harrell says. "The ghetto-fabulous lifestyle, the dressing up and going to parties. I hire people who are of the culture we're trying to reach. He was someone who could take a nothing day and make it into a party—and get a lot of people to show up for it. And he was a good dancer, so he had a great sense of music."

Combs went on to make several albums of his own as a recording artist. He owns two Grammy Awards, including one for his biggest hit: "I'll Be Missing You," about the late B.I.G.

Acting and movie producing followed. By 1998, he'd launched his fashion line and, in 2001, entered the realm of television production with the reality series "Making the Band" for MTV. He's never looked back, and has never been busier.

His antennae are acute and he is always on the lookout for areas in which to expand his business. Harrell explains how Combs works. "Everything he sees, he processes: Can I? Should I? Do I want to...? He has a little more insight than other people about the way music says something about the people who like it—and that all those things can be turned around and sold to them."

Simms points out that, in an age when corporations and corporate leaders tend to subject new ideas to endless polling and focus groups to minimize risk, Combs is confident in his own taste and instinct.

"He doesn't mind being the first one out there with an idea," she says. "He has the unique ability to see trends early. He's first, fast and fearless. He's not afraid to move forward when other people would be, particularly going after an audience of millennials that have not been successfully wooed in the past. And he does it by understanding his audience."

Combs has always kept a busy schedule, and his ability to pack what seems like a week's worth of activity into every 24-hour period is a fact of life to the people he works with.

"He's human, I think, but if he ever gets tired, he doesn't let it show," Simms says. " ‘Tired rhymes with fired' is the saying. He's a bit of an urban legend—sort of the Energizer Bunny."

Combs does try to take time out each week to let go of business and just relax with his kids: "That was one of the things I hoped for when I moved to L.A.: that we were all together out here," he says. "It helped me get my priorities in order and focus on quality time with them."

Sundays are also his time for slowing down with a great cigar. Every Sunday he takes what he refers to as "me time," usually with a Cohiba, occasionally with a Montecristo. And sometimes he enjoys cigars during the week as well.

"That's the definition of a cigar for me: when you're comfortable, and don't want to feel stress," he says. "It calms the mind. It's something I've been doing for the past few years. I do my best to make sure I take that time."

Combs was mentored in the ways of fine tobacco by Larry Schwartz, who retired last year as president of Diageo North America. "He's like the godfather of the spirits business," Combs says with admiration of Schwartz. "He loves golf and smoking cigars. I'd go out on the golf course with him and he'd give me knowledge. I noticed that, at the end of the day, he'd smoke a cigar. And he would teach me how to do it. I learned that there's an art to it, from the way it's lit right down to the ash itself and the length of the ash."

He smokes with friends like rapper/business executive Jay-Z (who appeared on the cover of this magazine in 2009), music executive Steve Stoute, as well as rapper Nas. He associates smoking cigars with being "a mogul, a boss, a giant. That's who smokes cigars."

Of course, other people smoke cigars as well. "One of the first times I tried a cigar, a girl gave it to me," he says. "That's the sexiest thing, to see a woman smoking a cigar—and to have her share one with you."

His preferred brand is one that is familiar to all cigar lovers. "I was in the Bahamas at a friend's house. I had a great view of the ocean. I put my chair in the center of the veranda and enjoyed a Cohiba. It's probably a little bit of a cliché, but I figure I started out with one of the best. I took my time with it and just enjoyed it."

Combs is eager to study the culture of cigars, and despite having smoked for some time, he still considers himself a student of the hobby. "From afar, I never understood cigars. Now I'm excited about the journey, about learning more about them."

Music is at the center of everything he does, so Combs looks genuinely perplexed when asked what he'd be doing now if he hadn't found such an instant foothold in the music industry. Then, without hesitation, he says, "I would probably be successful in some area of business, whether it was the nightclub industry or real estate. I'd be a businessman.

"But I never imagined music wouldn't work out. It felt so much like what I was supposed to do. It was hard to imagine doing anything else."

He is getting ready to record what he says will be his last album and vows to devote full-time to that process while it's going on, even leaving the connected world behind. "I lock myself in the studio so I've got 100 percent focus," he says. "I can't even have a phone. If there's a 911 call, they know how to get a hold of me. Otherwise, I just disconnect from the world."

Combs is well aware of how quickly fashions change in the music industry; among other effects of the Internet on the music business (which have been huge), the viral nature of hot new work via social media means that careers rise and fall in the space of months, even weeks.

"Now there are so many young, young artists in the industry," he says. "The age of the talent keeps getting younger. There are kids who are 13 who are ready—right now. The whole industry is getting younger."

Yet Combs has no fear about his ability to establish a connection with an audience the same age as his children, even as he reconnects with his long-time followers. It's been six years since his last album, 2010's "Last Train to Paris," though he released a mixtape album last year. But each year can be a lifetime in the attention span of that young audience.

"The way I have to come back is exciting to me," he says of the album, tentatively titled "No Way Out 2," as a nod to his first album, "No Way Out," in 1997. "If you're not putting out albums all the time, you have to come back in a way that grabs attention. People are always looking for what's next—but the cream always rises to the top.

"I'm going to make it the most honest and best that I can. If I can be fearless with it, nothing can stop me."

Harrell, for one, has no doubt that, once he sequesters himself in the studio, Combs will kill it and go out on a high note. Nor is there a question in his mind that a millennial audience will respond to the music of a middle-aged businessman.

"When you're cool, that's not something that dies away," Harrell says. "That doesn't get old. You're just an old cool guy. Sean's got an edge; he knows young people. He took a page from me and keeps a lot of young people around him."

"I'm a 33-year-old trapped in a 46-year-old's body," Combs jokes.

Why stop making albums and performing as a musician now?

"I want to stop at a great place," he says. "And a final album is a great place to stop. I want to take a victory lap, to do a world tour and really enjoy it one last time. And then I want to do different things and have different experiences."

One thing to which he'd like to devote more time is acting. Since he moved from New Jersey to Los Angeles (where he bought a European-style villa near the Playboy Mansion in Holmby Hills for an estimated $40 million in 2014), he's been eager to get back to movie roles, particularly given the wherewithal of his own production company. But he wants to do it right.

"Coming out to L.A. and being around the art of acting, I realized it's something you can't have one foot in and one foot out," he says. "So I'm going to put out my last album and devote 100 percent of my time to doing films."

His experience working on Broadway in 2004 gave him increased respect for the craft. Doing eight shows a week in a straight dramatic play—not to mention a much-venerated classic—is much more intimidating, he admits, than doing a live concert.

"I've jumped out of an airplane and this was way scarier," Combs says. "It was standing-room only. And there's nothing harder than live theater. I had a great coach pushing me. Every night, I was trying to figure out how to find that freedom and nakedness, to find that character and deal with his insecurities. I mean, two of my costars won Tony Awards. It was one of the most beautiful experiences I've ever had.

"I feel honored even saying that I stood on a Broadway stage in this play by Lorraine Hansberry. That's crazy."

Having surmounted most of the challenges and achieved more than he ever imagined, Combs shows no signs of flagging. At this point—in the middle of a life of which half has been spent at the top of the heap—is there anything he hasn't done that he still would like to do?

"Retire," Combs says. "I want to enjoy my family and my kids. What would I do if I retired? I have no idea."

In the end, he says, his legacy is his music.

"When I'm gone, only the songs will survive," Combs notes. "I know I'm making music that will live on. I don't go into the studio just to be hot, or to hear myself on the radio. Michael Jackson, Tupac, Biggie—part of them lives on in their music, even though they're not here anymore. That's really deep, man. The only other thing like that is religion. People will be singing those songs forever. The music will be here after I'm gone. And that's a lot of power."

Contributing editor Marshall Fine writes about film and entertainment at https://www.facebook.com/hollywoodandfine.