Chairman of the Board: Jay-Z

"No, grown men don't roll to clubs with entourages," asserts hip-hop mogul Shawn C. Carter, lounging his slim 6'3" frame on a plush, chestnut-colored couch in Chicago's opulent Peninsula Hotel. It's an understatement to say that he's understated (a ying to P. Diddy's richer-than-thou's yang, if you will), and today he's wearing a slightly wrinkled white T-shirt and black sweats. Unlike other hip-hop demigods that I've come across over the years, from gang-banging thugs to the more lauded and socially conscious, there are few pretenses with him. And refreshingly, the rapper we know better as Jay-Z -- who is kicking off the Best of Both Worlds tour in co-headliner R&B crooner R. Kelly's hometown -- isn't blinging quite as brightly as his more flamboyant counterparts in the game. Instead, he's celebrating his transition from street hustler to multi-platinum-selling recording superstar to music industry executive and, beyond that, to becoming a brand. And he's doing it his way -- as incognito as he can.

That fits. Carter is a three-time Grammy Award-winning artist, known for being a smooth, nearly silent operator. "I've always been more observant than talkative," he explains. "That's how I got the name Jay-Z from Jazzy. When I was a little kid, I was cool. They used to say back in the day, 'That little kid is jazzy; he's smooth.' That's how I took the 'Jay' and the 'Z.' Besides, I didn't like the name Jazzy growing up, because it turned out to sound flamboyant -- like Jheri curls and wearing purple silk." Ostentatious he's not, but he has got an eye for suits -- and his look is always crisp and cool.

Now 34 years old, the ferociously gifted rap artist took part in cementing hip-hop culture's place on a national scale, making it as American as apple pie and the ethos of Republicans. What could possibly be more American than the social values and political apathy hip-hop has come to embrace in the last few years? And, ironically, what youth movement in this country's short history has been able to have an impact on pop culture globally in the same way as this product of the Reagan administration? Hip-hop is a force that has evolved into a big business, often producing one corny product after another. But Shawn Carter's American dream comes in a package wrapped unlike any other luminary's in the field -- with street credibility and a proven multimillion-dollar track record.

His road to maturity has had its share of mishaps. Two years following the death of the Notorious B.I.G. in 1997 (Jay-Z's teenage friend and George Westing House Technical high school classmate), the artist who's also known as Hova and Jigga ran into some trouble. Jay-Z was accused of stabbing record executive Lance "Un" Rivera at Q-Tip's Amplified listening party. The same year, Jay-Z and DMX wrapped up the Hard Knock Life tour with no incidents of violence, donating a portion $18 million gross to the families of the Columbine victims.

Carter eventually pleaded guilty to misdemeanor assault and was sentenced to three years probation on October 11, 2001 -- two months after he released The Blueprint. Earlier that year, one of Jay-Z's bodyguards was found with a loaded gun when they were pulled over after a performance at Club Exit in New York City, resulting in the rapper's arrest for criminal possession of a weapon in the third degree. And still, Jay-Z managed to come out on top. Most albums became casualties of the post-September 11th economic crises, yet The Blueprint, according to Soundscan, went on to sell two million copies. Proceeds from the tour went to the families affected by the World Trade Center tragedy. Jay-Z is a true believer in karma.

But there's a flip side to moneymaking. Now that the rapper has real wealth and hip-hop is becoming so damn Republican, what with the genre's wealth obsession and emphasis on the individual, does Jay-Z aim to keep up with the Bushes?

"That's real, but I can't do it as much as Republicans cater to the upper echelon of voters," he explains, laughing. "I've been poor and I've gotten money." In fact, he's got so much money that he will not talk about his personal net worth anymore. "After you've had money, you start thinking about how to change things, [about leaving a] legacy," he says. "You start thinking past just having money, but when you first start getting paid, it's natural -- you're supposed to act a fool!"

If there is a legacy to impart, the ideal one these days is taking part in the electoral process. With the upcoming election, Jay-Z is rallying people of the hip-hop generation -- whatever that means nowadays -- to vote. "I used to always think, 'Why are we voting in the black communities? No matter who's in office, nothing happens for us -- it don't trickle down to where we live.' However, now I realize that if we do give our opinions and lend our vote that will put us in power. When our voice is heard, then that becomes power." And Jay-Z should know about power. The year 2003, when he decided he wanted out of recording studios, proved to be his most lucrative thus far.

That was the year Reebok made Jay-Z the first hip-hop artist to land an endorsement deal for his own signature sneakers. In a matter of days, the shoes in the S. Carter Collection became the fastest selling in the company's history, at $150 a pop. In the same year, the artist, who has engaged in lyrical scrimmages with rappers Nas, Fat Joe, 50 Cent and Prodigy, announced his impending retirement (again) with the release of The Black Album.

He's been threatening retirement since he began his career eight years ago, so why take him seriously nine albums later? Staring blankly at the latest Ashlee Simpson video on MTV, Jay-Z cites the need to be challenged in an otherwise static hip-hop world, and to take his career in a more personal direction. "The problem with hip-hop is that people are afraid to grow with the music," says Carter. "We cater to a young audience." This, despite the latest urban trend in which artists like Nelly and R. Kelly are catering to both the young fans and the older generation -- the ones who ushered in the culture decades ago. Jay-Z has both literally and metaphorically traded in his jerseys for business suits, stating, "As you grow as a person you start to view life differently -- not just rap -- and that's what happened to me."

Maintaining that he wanted to go out on top, Jay-Z hosted a sold-out benefit for Russell Simmons's Hip-Hop Summit Action Network at Madison Square Garden last year. It was the impetus behind Fade to Black, the Paramount Classics documentary about the concert that will be out this month. In 2003 Jay-Z also opened 40/40, a sports bar/club located on West 25th Street in Manhattan. One night while he was hanging out in the bar's V.I.P. room, New Jersey Nets point guard Jason Kidd dropped a jewel in his ear: He told the rapper that the Nets were for sale. "I laughed really hard," Jay-Z recalls. "I thought it was a joke and forgot about it. Then someone contacted me." After much speculating in the press on whether he'd be able to pull it off, Jay-Z is now part owner of the basketball team. And he's moving them, along with his partners, to a yet-to-be-built stadium in his native Brooklyn. "Jay-Z and I bonded right away," says Bruce Ratner, the rapper's partner in the Nets venture. "He's a proud Brooklynite who feels like I do: that the Nets will provide a new-found hometown spirit for the borough, especially for kids."

Think of Shawn Carter -- whose estimated worth is, according to Fortune magazine, $286 million -- as having the potential to become the Bill Gates, Oprah Winfrey and Russell Simmons of tomorrow. Plus, he has "the hottest girl in the game," siren Beyonce Knowles "wearing [his] chain." The father of all hip-hop moguls, Russell Simmons, believes that Jay-Z is hip-hop's greatest inspiration. "He's not following in my footsteps," writes Simmons via two-way. "He's leading me."

In his evolution from rap superstar to music executive and nightlife impresario (he's expanding 40/40 to Atlantic City this month), Carter is quietly building an empire. He already co-owns Roc-A-Fella Records, Roc-A-Fella Films and Rocawear clothing, built from the ground up with partner Damon Dash. Now, Carter is finishing his autobiography, The Black Book, with journalist/filmmaker Dream Hampton, and he is planning to launch a clothing line next year, fashioned after Ralph Lauren's exclusive Purple Label. "If you're not challenging yourself, you might as well be dead," says Carter, though "right now, I don't really have any goals. I've reached all the goals I set for myself. I feel like I'm in bonus coverage."

In as much as Jay-Z the artist is fulfilled, his alter ego Shawn Carter is at peace with his life. He's exorcised his demons, most significantly reconciling with his father whom he's dissed on track after track because he left the family when Carter was only 11 years old. Twenty years later, in 2002, they reunited in Carter's home, where the men were able to speak frankly in hopes of maybe starting over. "He passed a month or two after we talked," says Jay-Z. He pauses to think, adding, "I looked at it more as being a powerful day than being a sad day for me. I was like, 'Why did we meet then, this year?' There must have been something to learn from that. I was able to tell [my father] how I felt and put those negative feelings to rest. I was in the process of getting him a place, buying furniture when he passed. His liver was messed up, and they told him not to drink, but he continued to drink until he expired." We all make choices in life and, Jay-Z laments, "that was his."

Still, in typical hip-hop fashion, controversy is never too far away from the rapper. He recently released the collaborative album he produced with R. Kelly titled The Best of Both Worlds: Unfinished Business, with 11 new tracks. Kelly -- whom Jay-Z once distanced himself from when the singer was brought up on charges of child pornography -- is now embarking on a 40-plus-city tour with the hip-hop artist. "Far be it from me to judge a man who hasn't been found guilty," says Jay-Z. And if he's found guilty, the rapper believes, "he'll have much worse troubles than going on tour with me."

And then there are the contradictions. If, atypically, Jay-Z rolls sans entourage, why is it that his constant companion is a seven-foot-tall bodyguard? "You have a lot of people who think they know you because they listen to your music all day," he responds, slightly animated, "and if girls like your music, they can get excited. Sometimes they might even snatch your clothes off or something." Oh, we get it. It's for protection against excited women, because hip-hop bodyguards couldn't possibly be used for fronting.

For instance, just two, maybe three years after releasing 1996's instant classic Reasonable Doubt, the urban legend in the making, hailing from Brooklyn's despondent Marcy Projects, was as usual moving about New York City by himself. He wound up, as many hip-hop royals did at the end of the last century, at Club Cheetah, located in the Flatiron District in Manhattan, to listen to music, have a drink and then move on to the next hotspot. But Jay-Z was so detached from his growing celebrity that he couldn't imagine what would happen within the next hour or so. "I had a [Latrell] Sprewell jersey on, and as I'm leaving, these girls from the club came and got me," he says. "They [stood] in front of me and started going craaazy and ripped my jersey." But the most shocking aspect of the assault on the self-professed "greatest rapper alive" by the coop of overzealous chicken-heads was where it took place. "This was the craziest thing that ever happened to me. What was even crazier was that it happened in New York City, because everyone is too cool to be trippin' at home."