One in an occasional series marking the 30th anniversary of rap music

On his desk in his corner office is a fruit plate, prepared for him by his at-home chef and served to him by one of his harried personal assistants, the one who never has time to eat and who lost 15 pounds in the first month on the job. Damon Dash -- CEO of the "Roc," Roc-A-Fella Records, Rocawear Clothing, Armadale vodka, Tiret New York watches and Dash Films -- sits, picking at the tropical fruit, baseball cap swung backward, diamond stud blinging in one ear. Holding court.

First, he summons the music guys: "Ah, here we have the no-hit team." Dash kicks out a reporter and shuts the door to his office, and the hollering commences. A few minutes later, Dash flings open the door and orders everyone, the music folks, the fashion folks, the sneaker folks and the advertising folks, inside. EVERYBODY.

NOW.

Dash, 33, Harlem-born and prep-school-bred, may oversee a $500 million hip-hop empire, the one he founded in 1996 with his friend, Grammy-winning rapper Jay-Z. But as he sees it, the devil -- him -- is in the details, and if he doesn't keep an eye trained on every aspect of his companies, then who will? These days, he's got more than his share of pressure. Jay-Z, the man upon whose back Dash built his fortune, says he's retiring. He's facing serious legal problems, including a civil lawsuit brought by a woman who accuses him of sexually assaulting her in Brazil, an allegation he vehemently denies.

And he's in negotiations to sell Roc-A-Fella Records.

Life at the top can get awfully complicated.

"Pay attention," the single father of two says. "This is very important. Sneakers are very important."

Indeed, sneakers are everywhere, piled up on the window ledges, all in size 91/2, and all laced just the way Dash likes them. He parades about the room, modeling sneakers, soliciting opinions, answering his cell phone, berating those whose attention wanders.

Dash knows from sneakers; never wears the same pair twice. In the $10 billion game of hip-hop -- which turns 30 this year -- where Run-DMC immortalized "My Adidas" and Heavy D rhapsodized about Nikes, it pays to be branded. Dash knows this, and in his unceasing quest for -- we're not making this up -- "world domination," he's just acquired Pro-Keds for an undisclosed sum. Still, the sneakers are just one line item on his acquisitions docket.

By 6 p.m., on a summer weekday, there are 23 employees crammed into Dash's office.

His attention span is at once manic and focused, flitting from one subject to the next, daring his underlings to keep up.

The men in the group struggle to match wits with him, but he's like a mother lion, distractedly swatting away at her cubs.

The verbal sparring escalates until, in a flash, Dash and one of the music guys, the burly one, are "play" boxing, trading blows around the sneakers as one of Dash's female assistants bounces up and down, squealing, "Omigod. Omigod. Omigod."

Another day, another dollar.

It's All Good

The latest office boxing match leaves Dash with a broken finger. But what better release can he find for his restless energy? With 20-hour workdays, work and play often morph into one: Partying is part of his work -- "I'm selling my reality" -- and to him, work is a party. And it never ends. He can't look at a business opportunity that feels right, he says, and not jump on it. (He even satirized his thirst for corporate conquest on "Chappelle's Show," where he hawks Roc-A-Pad sanitary napkins.) So he's not complaining. Working like a maniac, barely having time for a shower, needing hired help to remind him it's time to eat? It's all good. It's so good.

"I look at myself like a rock star," Dash says. "I have fun and laugh most of the day. But I got to work."

Indeed, the workaholic Dash is one of a trio of hip-hop impresarios at the top of their game, men who've mastered the work/play dichotomy and turned their Cristal-soaked lifestyles into cold cash: Def Jam's Russell Simmons, Sean "P. Diddy" Combs of Bad Boy Records, and Dash. They started out in music, toiling behind the scenes rather than in front of the mike (only Combs has gone from producing to performing), polishing talent so that others may sparkle. From there, it was a natural progression to peddle other aspects of the hip-hop culture -- clothes, liquor, jewelry, sneakers, movies -- to a public eager to wrap itself in the perceived accouterments of the "urban" lifestyle.

Back in '74, when DJ Kool Herc first started marrying rhymes to beats, no one else took the music seriously. But they did, the men and women of hip-hop, selling mix tapes out of car trunks, pressing records themselves. If no one else cared, so what? They were doing it for themselves, representing for a culture, hip-hop.

And along the way, they got paid.

Making money seemed like a revolutionary act.

"People like Russell and myself, and Puff, we just saw that niche and that opportunity," Dash says. "It's new music, there's no real protocol for it. A lot of people have been exploiting and capitalizing off of our culture and it hasn't been us. And we've been able to be put in a position where we can be the businessman.

"We've made it cool to be the CEO in the 'hood. We made it cool to be smart."

There's Roc-A-Wear clothing, the Roc's cash cow, raking in an estimated $350 million a year and ranked No. 2 in retail sales by industry analysts in the urban wear market this year, sandwiched between Simmons's Phat Farm and P. Diddy's Sean John labels. There are the sneaker lines, Pro-Keds and Roc-A-Wear. There's Roc Digital, the electronics company recently launched, featuring MP3 players. There are Dash's film companies, which have produced five films in five years: Roc-A-Fella films, which cater to the rap music demographic; and Dash Films, which co-produced "The Woodsman," a November film starring Kevin Bacon that is generating festival buzz. (This year Dash directed "State Property II," due out in 2005, and is slated to direct "Iced.") Then there's America, a glossy, coffee-table magazine that rhapsodizes about the urban life. And Roc-A-Fella Records is expanding beyond its rap roots to incorporate rock and R&B artists like Ronson and Nicole Wray.

Of course, as Dash's empire expands, others ask: Who really benefits?

"Hip-hop has definitely provided opportunities for entrepreneurship," says Yvonne Bynoe, president of the Brooklyn-based Urban Think Tank. "My question has to do with the long-term gains. . . . As a purely business consideration, I think these guys are fabulous. But the problem I have is they make it seem like this is tied to some larger hip-hop audience."

African Americans in the inner city, she says, don't win the wealth. More often than not, the products aren't sold in the ghetto. And in the corner offices of these "urban" companies, the faces of the publicists, the lawyers, the dealmakers are frequently white.

Mention this criticism to Dash, and he bristles.

"I'm benefiting," Dash says, "I'm black. We market to all demographics."

He's annoyed, he says, because no one questions whether an Italian-owned company is benefiting the Italian community. Why is a different standard placed on black-owned businesses? He says he puts money back into his community, with his charities such as Team Roc, a program that combines basketball and academics to reach inner-city kids, and his participation with the politically focused Hip-Hop Summit Action Network, which he started with Simmons.

As for the Roc, many of the faces there are indeed white, from his assistants to his vice president of Dash Films, sprinkled in with Asian, Latino and African American faces.

Dash says that many of his employees are friends he grew up with back in the day. That means a lot to him, he says: "I want you to get rich. Spread it around. No matter how arrogant you may be, people'll love you. They'll be like, 'But he got everyone around him rich.'

"I'm not saying that everyone has to want what I want, but if you work with me, You. Have. To. Want. To. Take. Over. The. World."

Dash for Cash

Yes, he's a product of the inner city. Yes, he grew up with his dad largely absent. But Dash isn't someone who so easily fits into tidy stereotypes of ghetto dwellers who yanked themselves up by their Nike straps. His mother was a travel agent and an entrepreneur; he grew up middle-class in East Harlem, went to private school and tooled around town in a Nissan Maxima. He grew up hustling, yes, but hustling meant throwing parties and managing fledgling rap groups, the better to fund his lavish tastes.

Still, his wasn't a trouble-free adolescence. By his own account, he was a wild kid, a restless sort who got kicked out of the Dwight School for bad grades and bad behavior. His mother died of asthma when he was 15. And in 1987, according to court documents obtained by The Washington Post, he allegedly raped a 14-year-old at a summer camp in New York. He was 16 at the time.

According to the civil lawsuit, Dash had been "dismissed from the summer camp program . . . because of his unruly conduct, aggressive behavior and violence." The camper alleges in her complaint that he returned to the camp, where he assaulted and raped her. The case appears never to have gone to trial. (When asked generally about the case, Dash says, "Someone accused me of doing something that I didn't do and it was thrown out of court." Dash's publicist did not respond to repeated requests for comment on specifics of the civil case. Efforts to confirm the details with the camp were unsuccessful.)

In 1988, the same year the civil suit was filed in New York County, Dash went to boarding school on a scholarship.

There, he learned to traffic in contradictions.

At South Kent, an all-boys' school in Kent, Conn., Dash was an average student, a khaki-clad preppie who took up lacrosse. At home, he boxed at the Boys Club and ran with the rough boys.

"I dealt with the illest murderers and street guys that you could ever meet," he says. "And I survived. And I also survived the preppiest, richest, snobbiest, most prejudiced individuals as well."

Paul Abbott, South Kent senior master, remembers a "charismatic" kid from "difficult circumstances," a kid who was passionate and outspoken, a kid without a mother, a kid without moorings.

"There were a lot of things that were going on at home that made his time with us one foot in one pond, one foot in the other," Abbott says.

Indeed, Dash's stay at South Kent was short-lived. His upperclassmen friends had all graduated; the kids left behind were "corny," he says, innocents who couldn't begin to fathom where he came from. So he dropped out after a year, getting his GED back home in New York.

School wasn't the priority; making money was.

He's a "cakeoholic" -- that is, someone who's addicted to earning (and spending) massive amounts of money. He is, after all, a child of a certain kind of Harlem, nursed on the glamorous life, where being "flossy" is a virtue. Where the more money you have, the more you realize what you don't have.

"At first," Dash says, zipping through Manhattan in his custom-fitted, chauffeur-driven van, "I aspired to ride first-class.

"But once I rode a private jet, it was like first-class is disrespectful and demeaning to me."

He makes these statements without the slightest bit of irony. Indeed, his ego is notorious. Witness him dancing around in his artists' music videos, holding aloft bottles of Armadale vodka.

"Damon is his own biggest fan," says Toure, Rolling Stone contributing editor and former host of MTV2's "Spoke N' Heard."

"He's certainly not going to ever hesitate to tell you how smart he is, how rich he is. . . . He couldn't be more self-confident, and in hip-hop, that's a virtue."

From the start, when he went to a Heavy D party in the early '90s, Dash was fascinated with the glamour of rap, the girls, the power, the rush of living under the klieg light of celebrity. With his cousin, Darien Dash (brother of actress Stacey Dash, co-star of "Clueless"), he formed Dash Entertainment, representing fledgling rap groups.

"I used to make fun of him," remembers Kareem "Biggs" Burke, co-CEO of the Roc, who met Dash when they were in high school.

They didn't understand his musical taste, particularly the appeal of a former hustler from Brooklyn, Shawn Carter, who went by the moniker Jay-Z. Dash mainly repped the "backpack rappers," those whose forte was technical skill, MCs who could turn a rap about basketball into a display of lyrical virtuosity, a symphony of rhyme, rhythm and flow. But the early '90s was the era of gangsta rap, with Dr. Dre, the late Eazy E and Snoop Dogg rapping about hard life and hard times. Then, in the early '90s, Biggs heard Jay-Z battle DMX in a rhyming battle, and he was converted. Listening to Dash talk on and on about how, with Jay-Z as their ticket, they could create an empire, Biggs was even more convinced.

"He was saying, 'Yo, we can have a clothing line, music, we can have a bunch of things and just branch off,' " Biggs remembers. His other friends didn't get it, he says, "but I thought he made a lot of sense."

So in 1995, they formed Roc-A-Fella Records, pressing records themselves and selling them out of the trunk of their cars, and pushing radio shows to play their music. They were loud, they were everywhere, buying out the bar and promoting the glamorous life.

"They started their own label when it was hard to do that," says Toure. "They had an aggressive, boisterous way. . . . And they made it work."

Jay-Z's first album, "Reasonable Doubt," released in 1996, sold more than a million copies. In 1997, Roc-A-Fella entered into a 50-50 partnership with Def Jam/Island Records, a partnership that gave them both the heft of corporate financing and no small amount of independence. The label expanded to include other talent, like Beanie Sigel, Cam'ron and M.O.P., and launched the performance career of former power producer Kanye West, whose 2004 debut album, "The College Dropout," has sold 2.1 million records to date, according to Billboard senior analyst Geoff Mayfield. Today, Jay-Z alone has sold over 17 million records.

"They really came into the industry with a chip on their shoulder," Toure recalls. "I remember Damon talking, 'We don't want the nigger deal. . . . You're giving us the best deal.' "

Others, Toure says, were just happy to have their song on the radio, thrilled to be in the game, " 'Omigod, we were on MTV. . . .

"These guys were never like that. They were like, 'Omigod, we're going to get paid.' They definitely had their eyes on the prize."

Trouble Afoot

Times have changed. Jay-Z has announced that after a decade of rapping, he will retire from the business after the release of his latest CD, "The Black Album." Says Biggs: "He's getting old." (Jay-Z is 35.) "Retirement" seems to be a fairly loose concept. Recently, Jay-Z announced that he will embark on a more than 40-city tour with the legally challenged R. Kelly. (Jay-Z, through a publicist, declined to be interviewed for this article.)

The tabloids are rife with reports of tensions between Dash and Jay-Z, of the latter defecting to form his own label. But Dash insists that the two are still friends. "It's kind of obvious by his new demeanor that he's not as involved with us anymore," he says. "If he chooses to be an independent entity, that's fine. I choose to stay with the Roc."

Apparently, staying with the Roc means unloading part of it. With the exception of the wildly popular West, the other artists don't have the selling power of Jay-Z, whose last album sold 2.7 million records. (Beanie Sigel, who beat an attempted murder rap last year, sold 552,000 records with his album "The Reason." Cam'ron, recently signed to the Roc, sold 458,000 copies of his album "Confessions of Fire.")

Dash has been in negotiations to sell the company to Universal; he says it's a smart business move. You don't hang on to a business forever. You create a business, you have success, you negotiate. It's how you get a check.

These days, he has had to focus on more than just getting a check. He's reportedly back in the courts, fighting with the mother of his son over custody. He's being sued by Tony Mason, an acquaintance, for allegedly assaulting Mason on two different occasions, according to the complaint, one of them once on the set of the 2002 film "Paid in Full," which Dash produced. ("I defended myself, but I didn't assault him," Dash says.) Mason's lawyer says the case is scheduled to go to trial Nov. 15.

His latest legal troubles are a bit more dramatic. He's been sued by Kirstie Thompson, a sometime model. In her complaint, she accuses Dash of assaulting her by forcing her to have sex with him after a New Year's Eve party in Brazil in 2002. According to her attorney, Raoul Felder -- the celebrity divorce lawyer who has represented David Gest and Rudy Giuliani -- Thompson filed a complaint with the Brazilian police and then left the country.

It's a case, in the wake of the Kobe Bryant drama, tailor-made for the tabloids: rich man, pretty woman, explosive allegations.

When asked about the case, Dash becomes upset.

"Nothing happened," Dash says, his voice rising. "It looks like a publicity stunt to me. . . . I respect women 100 percent. . . . No check has been cut by me and I would never settle. . . . It's felonious [expletive]. . . . Why would I ever settle for something that I didn't do? Ever in my life. Ever. Ever. Ever."

Thompson's lawyer, Felder, says of the civil case: "We have witnesses in New York. . . . There's no question she had champagne, but that's not a license to be raped."

The lawsuits, Dash says, are the cost of being a public figure.

"There are no criminal charges. . . . Just another case of someone trying to get a dollar."

Traveling With the Posse

It takes a village to take care of Damon Dash.

Dash is a man who lives surrounded by people, and a good number of those people happen to be women.

He has lost the two loves of his life: His mother, Carol -- "I was always the kid that was crying for his mother" -- and Aaliyah, the singer-actress who was killed in a plane crash in 2001. The two had talked of marrying, if they could coordinate their schedules. He misses her still. Now, he says, he focuses most of his attention on his two children, 12-year-old son Boogie, of whom he won custody after a virulent court battle; and 4-year-old Ava, his daughter from another relationship, who lives around the corner. He wouldn't mind being in love again, even though these days, regarding matters of the heart, he mostly plays the field. (Last year, British tabs went into a frenzy over his alleged relationship with the very married Victoria "Posh Spice" Beckham, who was the spokesmodel for Rocawear.)

Today, at his cavernous TriBeCa loft, the field is pretty crowded, with nearly a dozen people, mostly women, hovering as Dash breakfasts, a pretty young model-actress gazing raptly as he frets about needing to mediate a contretemps between friends. ("But that's so dangerous!" the model-actress exclaims.)

It's time for a road trip, but he's having trouble getting out the door. There's an impromptu fashion meeting to oversee, phone calls to take, a dinner party to plan.

Finally, he finishes eating, says goodbye to the young model-actress and checks his blood-sugar levels with a tiny portable testing kit (Dash is diabetic) and then he's out the door, two assistants, a mohawked videographer, one of his senior VPs and a reporter in tow. They pile into Dash's van, a cushy leather affair outfitted with a queen-size bed in the rear.

Everyone crams into the few available seats, with Dash's bodyguard riding shotgun in the front, next to the chauffeur.

Damon sprawls out in the bed, nestled amid a pile of snowy white pillows and blankets.

Today's trek to Philadelphia is to check on the progress of Dash's latest investment, "Shadowboxer," which stars Helen Mirren and Cuba Gooding Jr. in an improbable pairing as an interracial and incestuous mother-son team of assassins.

Films fascinate. There is the sense that film is the arena that eludes him, that he can't stand being the kid left out of the game.

Years later, he's still chafing at the "very disrespectful treatment" he received from the suits at Dimension, which distributed "Paid in Full."

"He's pre-labeled," "Shadowboxer" director Lee Daniels says. "Because he's rap. Because he's alleged gangsta. We're getting ready to show what alleged gangsta rap can do. Which is serious art."

On the set, an old school auditorium, Dash jokes around with Daniels and actor Stephen Dorff. He's intently focused, concerned, solicitous with Daniels, a kinder, gentler Dash. His only gripe comes when he watches the dailies of Gooding performing a strip dance to an old rap tune.

"Yo, why'd you have to use Nas?" he asks, referring to a rival rapper of Jay-Z's.

An hour or so later, back inside the van, Dash nestles back in his bed, ready for a nap. Music plays in the background.

Except that sleep eludes the ever-restless Dash.

"Play that again!" he demands.

The volume cranks. Heads bob. It's been a long day, and everyone's getting a little loopy, deconstructing the lyrics to the Beatles' classic "I Am the Walrus," a song that some speculate is about, fittingly enough, John Lennon's disillusionment with pop life: What does this song really mean? What's up with the Eggman? Koo Koo K'Joob?

Then Dash starts speculating about making a movie based on the Walrus. They would all be spies with cool code names. Sofia, one of his assistants, would be Koo Koo K'Joob.

And Dash would be the Eggman. No, no, no, he'd be the Walrus. Or are they the same thing?

They play it again and again. The orchestration swells, the strings gaining in intensity as the song sweeps and swells through the darkening van as it speeds up I-95, through the Holland Tunnel and back into TriBeCa, back to Dash's loft with its pinball machines and Roc-A-Wear ads. Everybody sings along.

"I am the Walrus!" Dash chants, pointing at his chest, head bobbing, body bouncing.

"I am the Walrus! I AM THE WALRUS!!!!!!"

"Koo koo k'joob, k'koo koo k'joob!!!"

Researchers Meg Smith and Karl Evanzz contributed to this article.

"We've made it cool to be the CEO in the 'hood," says Damon Dash of steps he and other rap pioneers took to build businesses that comprise records, clothes, movies and more. Dash at his TriBeCa loft in New York and at a hip-hop summit, left, last month in New Jersey to discuss issues of concern to young voters.Dash travels and operates his businesses the same way: in style. At his Rocawear office, right, he presides over companies that rake in an estimated $500 million a year.