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e waited until the bus was ready to leave before squeezing up front to address the passengers. The Greyhound was going from Chicago to Indiana. It was winter. The sky was suffused with gray.
He surveyed the bunched rows of seats. There were only 19 passengers, most of them young, most of them black. Billy Wimsatt was white. It was an audience that made him especially comfortable.
He held aloft a slender book. "I wrote this book," he said over the chitter of talk. "It's pretty good. It normally sells for $12. On this bus, I'll sell it for $5, and you can read it along the way free."
It was called "No More Prisons," and was about incarceration and philanthropy and hip-hop, always hip-hop, for hip-hop was the everlasting undertone to his life. He was a writer and activist, and over the years his work had made him something of a minor cult figure in the hip-hop world, a white man with unusual credibility among blacks deeply protective of their culture. He was an unbudgeable optimist, convinced he could better the world by getting whites and people of other races to talk together and work together. He spent most of his time on the road, on a yearlong tour of several dozen college campuses, preaching his message. Now the bus was taking him to Earlham College in eastern Indiana.
Some passengers gave grudging looks of curiosity. What gives with this guy? Six people beckoned for copies. One woman gave hers back after 15 minutes, opting for sleep. A man behind her bought one. A woman said she'd take one, too. "Cool," Mr. Wimsatt said. He gave her a big smile and a hug.
Billy Wimsatt was 27, still clinging to the hip-hop life. He didn't look terribly hip-hop, and not because he was white. He was balding and brainy-looking, with an average build and an exuberant nature.
He was born as rap music was being invented by blacks and Latinos in the South Bronx. What began as party music became their cry of ghetto pain and ultimately their great hope for a way out. And as hip-hop -- not just rap music but fashion, break-dancing, graffiti and the magazines that chronicle it all -- blossomed into the radiant center of youth culture, Billy Wimsatt and lots of white kids found in it a way to flee their own orderly world by discovering a sexier, more provocative one.
Like many young hip-hop heads, he regarded hip-hop, with its appeal to whites and blacks, as a bold modern hope to ease some of the abrasiveness between the races. Hip-hop, as he saw it, endowed him with cultural elasticity, allowed him to shed the privilege of whiteness, to be as down with blacks as with whites. For a long time, he felt black in every respect but skin color, he says, which was why he had been able to get away with that much-noticed article seven years ago in The Source, a magazine considered one of the bibles of hip-hop.
It was a withering critique of "wiggers," whites who try too hard to be black so they will be accepted. Soon, he argued, "the rap audience may be as white as tables in a jazz club." In the last paragraph, which The Source cut from the final version, he warned black artists that the next time they invented something, they had better find a way to control it financially, because whites were going to steal hip-hop.
"And since it's the 90's," he concluded, "you won't even get to hear us say, 'Thanks, niggers.' "
Yes, Billy Wimsatt seemed about as authentically hip-hop as a white guy could get. But as he slid into the complexities of adulthood, he said, he often found himself wondering if that was enough, unsure which culture was truly his. He had drifted a long way from his black hip-hop roots. Now, on these unsettled grounds, he was far from certain he could stay true to his ideas.
Nancy Siesel/ The New York Times
Billy Wimsatt embraced
hip-hop as a boy to slip the bounds of his whiteness.
A Believer on the Brink
On a clangorous Manhattan sidewalk, Elliott Wilson stopped to study the bootleg rap tapes splayed on a street vendor's blanket. Music emanated from a portable stereo.
"Some dope stuff here," Mr. Wilson, a gangly, light-skinned young black man with inquisitive eyes and a contagious laugh, said approvingly. The bargains got him pumped up. He peeled off a five-dollar bill and bought "Opposite of H2O" by Drag-On.
Elliott Wilson had never met Billy Wimsatt, but their lives had traced similar trajectories across the hip-hop landscape. As a writer and editor, he too had spent much of his adult life thinking about hip-hop. And not just hip-hop, but race and hip-hop. Race was unavoidable in hip-hop -- what with all those black rappers idolized by white teen-agers -- and like Billy Wimsatt, Elliott Wilson was preoccupied with that conjunction and what it meant in his own life.
Which culture was his was not Elliott Wilson's worry. Hip-hop had inspired him to believe that, precisely because he was black, he could achieve what whites simply assumed was theirs by birthright -- a gainful life over which he asserted control.
When he read Mr. Wimsatt's "wigger" article, he and a black friend were beginning their own hip-hop publication, Ego Trip. They saw it as a brash challenge to the established, white-owned magazines like The Source. Bubbling with assurance, Mr. Wilson had judged the "wigger" article amusing; for all its ridicule of whites, he had still considered it "a white boy's perspective on hip-hop." He certainly hadn't seen it as a prophecy of personal doom.
Now, he sometimes had to wonder. He was closing in on 30, trying to hold fast to his own idea of the hip-hop life. He had watched with anger and growing pessimism as Ego Trip folded and whites asserted ever-greater control over the hip-hop industry. Recently, he had become editor of a promising hip-hop magazine, XXL. It was white-owned. And so he wondered if he was selling out, if he would ever become what he wanted on his own terms. Was hip-hop his story, the black man's story, after all? Did hip-hop unite the races or push them further apart?
A White Boy Confined in His Skin
Growing up in Chicago, Billy Wimsatt remembers, he believed the only way he could have a good life was to be black.
His own life felt proscribed. He was an only child. There was rarely music in the house, just the droning news stations. He saw an awful lot of "Nova" on PBS. He was to avoid the unsavory black neighborhoods.
Yet, he recalls, black children seemed to roam freely. They seemed to grow up faster. In fourth grade, his teacher asked if anyone baby-sat. A black girl's hand shot up. Incredible. Black girls were mature enough to baby-sit. He says he longed to live in the projects.
Where he lived was the integrated neighborhood of Hyde Park, in a perfectly diverse six-flat: two white families, two black, two mixed. His father taught philosophy of science at the University of Chicago. His mother was sort of a perpetual student.
At his mostly white private school, he was not especially
popular. He imagined becoming a computer programmer, a
scientist, an astronaut. Then, in sixth grade, a black kid
told him to listen to a rap song, "Jam On It." "It was like a
message from another world," he said.
Nancy Siesel/ The New York Times
"My magazine isn't some
white-boy magazine," says Elliott Wilson, who has been
editor of XXL for a year. Still, "it can't be totally
black if a white man is signing the check."
Increasingly, he disconnected from a white culture that he equated with false desires. He had jumped out of his container, he said, "like spilled milk." After sixth grade, he persuaded his parents to transfer him to a largely black public school. The cool kids, he noticed, wore fat sneaker laces, favored gold jewelry, did graffiti. He began shoplifting fat laces, fake gold jewelry and markers and selling them to hip-hop heads.
He started break-dancing on the streets. And at 13, he began sneaking out at night and riding the trains with black and Latino friends, bombing the city with spray paint. Upski was his chosen tag. From then on, little Billy Wimsatt became Upski, one of Chicago's most prolific graffiti artists.
His frazzled mother, dogged by insomnia, would discover him gone at 2 a.m. She barred his graffiti crew from the house (one of them even burglarized the place), sent him to a psychiatrist, threatened military school. When he persisted, his parents plunked him back in private school. But he barely associated with white classmates, he says. Hip-hop had cloaked him in a new identity.
Astonishingly, and much to the dismay of many older people who abhorred its defiant attitude, its frequent misogyny, violence and vulgarity, hip-hop culture was becoming a great sugar rush for young people of all races. Before long, rap would eclipse country and rock to become America's top-selling pop-music format. And whites would be the ones buying most of those rap albums -- a full 70 percent.
For many, even most, young whites, hip-hop was ultimately a hobby, to be grown out of in good time. For Upski, it became a cause, especially as the late 80's gave rise to politically conscious rappers like Public Enemy, with its peppery blend of black nationalism and rebellion. "Once it became a pretty full critique of American life -- race, politics and political hypocrisy -- that's when it really registered with me," he said.
A Black 'Leader of the Nerds'
Elliott Wilson grew up in the Woodside Houses project in Queens, the oldest of three brothers. His mother was of Greek and Ecuadorean roots; his father, a printer from Georgia, was black. Elliott was very light-skinned, and his hair was different from the black kids'. When it came to skin color, he picked up some mixed messages.
He was 5 when his father told him: "You're going to be judged by who your father is. I'm black. So you're black. Accept it before you get hurt." And he did, he said: "I felt like the black man from the jump."
He also spent a lot of time with his father's mother. She was tough, and she had friends of all races. She called white people crackers, but told Elliott, "Never trust a black person darker than you."
Attending predominantly white schools, self-conscious about his looks, he never really fit in, he says, recalling that time now. The black and white students didn't mix much, and while the black football players were cool, he was no football player. Instead, he befriended the outcasts.
"I wanted to be a cool kid and I wasn't," he said. "But I didn't want to sacrifice who I was to fit into the system. I'd rather create my own system. I wasn't going to be a fake. So I was the leader of the nerds."
His parents sheltered him from the influence of the streets. He watched a lot of television. He loved "Happy Days" and "Good Times," admired Howard Cosell and imagined becoming a sportscaster. In high school, he says, he increasingly felt himself an outsider. His grades, always good, fell.
But there was hip-hop. Hip-hop was cool, and his growing love of it made him begin to feel cool. His parents bought him a set of Technics 1200 turntables and a mixer. On weekend nights, while classmates were out on dates, he would be home taping the hip-hop shows off the radio.
When he listened to Public Enemy, he began to shake his head knowingly. For young Elliott Wilson, unaware of so much, the group's powerful lyrics of oppression and rage, especially the album "It Takes a Nation of Millions to Hold Us Back," were an awakening to what it meant to be black in America. He got a Public Enemy jacket, with the group's logo on the back: a black man in the cross hairs of a gun.
He became more aloof. He no longer said hello to white people, even family friends, unless they greeted him first, he now says. They asked his parents, What's gotten into Elliott?
He went to La Guardia Community College -- in part because Run of Run-DMC had gone there to major in mortuary science -- and then to Queens College. He began writing for hip-hop publications. One day first semester, he had an interview with Kool G. Rap. School felt irrelevant. He walked out of class and never returned. He entrusted his fate to hip-hop, and hip-hop breathed possibility into his life.
"If I came out of school without hip-hop, I wouldn't have thought of owning my own business and having power," he said. "As a person of color, to be legit, you think you have to be a worker for someone. Hip-hop made me believe."
But hip-hop was full of bizarre crosscurrents. When he saw white kids simulating his behavior, he got annoyed. It was one thing if they had grown up in the culture. But those well-to-do young whites who tried to appropriate hip-hop for themselves, he says, were simply insecure "image chameleons."
Right here was the enigma of hip-hop: The black rappers certainly weren't preaching integration, inviting whites into their homes. They were telling their often dismal stories, the pathologies they felt had been visited on them by a racist system they yearned to escape. But so many white kids were turning that on its head. They wanted to live life large, the way the rappers did.
A Reason for Rhymes
The phone rang. Dog got it: "He here. We here. I'll hit you back later. You gonna be in the crib?"
It was afternoon. Like a lot of aspiring rappers, Dog and his friend Trife were living life small, passing time in Dog's rampantly messy apartment in Brooklyn's Clinton Hill section. Passing time was what they did most days. They played games, gossiped, drank Hennessy, chewed over the future. Weekends, they went bowling. They were 23, young black men seeking sanctuary from the streets by rhyming their lives.
With their friends Po and Sinbo, they had formed a rap group, Wanted and Respected. Dog's closet was stuffed with recording equipment; his specialty was creating the beats. He made some slim money doing tapes for kids with their own rap dreams ($100 a tape) and selling shirts on the street. The group had played a few clubs, always gratis. Others shuttled in and out, but life weighed on the composition: members kept getting jailed, and one had been killed.
Dog and Trife had followed a trajectory of intense poverty and outlaw life. Dog's grandmother basically raised him -- a dozen relatives packed into a three-bedroom place. Trife grew up with his mother, an R & B singer, and seven others in the nearby projects; he still lived there with her.
They had belonged to a gang called the Raiders, they said, selling drugs and doing other things that landed them in prison. If a white person came into their neighborhood, they said, they robbed him. They all packed guns. "It was bad as Beirut," Dog said. Trife said he still sold drugs, and some of the others did dubious things.
A few years ago, they gravitated to rap, embracing it the way so many poor blacks have long embraced basketball. But it was better. There were more slots. And it seemed to demand less talent. "You don't even have to sing well," Dog said.
"Music is my sanity," Trife said. "If I wasn't doing this, I'd probably be doing 25 to life."
Dog laughed. "If it weren't for rap, I'd be dead."
Many older blacks felt rap denigrated their race. They hated the constant use of "nigga" in the songs. Dog and Trife shrugged this off. Rap was raw and ugly, but that was their lives, they said. Rap was a blunter truth.
Dog found it curious that whites -- suburban mall rats,
college backpackers -- bought most rap records. "White people
can listen to rap, but I know they can't relate," he said. "I
hear rap and I'm saying, 'Here's another guy who's had it
unfair.' They're taking, 'This guy is cool, he's a drug
dealer, he's got all the girls, he's a big person, he killed
people.' That is moronic."
Nancy Siesel/ The New York Times
Dog, right, Po and Trife,
left, the members of Wanted and Respected, at a housing
project in Fort Greene, Brooklyn. Trife sees music as
his sanity. "If I wasn't doing this," he said, "I'd
probably be doing 25 to life."
Later, Dog said: "Hip-hop is bringing the races together, but on false pretenses to make money. Look at Trife. He's got two felonies. That means he's finished in society. But he can rap. His two felonies, in rap, man, that's a plus."
"It's messed up," Trife said. "In hip-hop, I'm valid when I'm disrespected."
Trife recited some lyrics he had written:
You can't walk in my shoes,
If you ain't lived my life.
Hustling all day, clapping out all night.
The Cool Rich Kids' Movement
The road to Earlham was speckled with billboards for Tom Raper RV's, the Midwest's largest RV dealer. The trees were sheathed in glass from the freezing rain.
Earlham, a small Quaker college, was predominantly white, marginally into hip-hop. Upski was to give a talk, accompanied by a hip-hop group, Rubberoom.
Upski had dropped out of Oberlin College in his junior year. He had only reluctantly gone to college at all. He spent more time doing graffiti and reading magazines than going to class. He wrote an anonymous column for the black paper that scathingly denounced white people. He had a hip-hop radio show: "Yo, this is live from Chicago." Many people thought he was black.
Even so, he says, he was sporadically queasy about his hip-hop moorings. He knew his infatuation with blacks could be taken different ways. He could be accepted as credible, or taken as exploitative.
"That is the great fear of blacks," he said. " 'Oh, you'll be fascinated with us, and then go back to dominating us and you'll be better at it because you'll have inside information.' " When he had shown drafts of his writings about race to a black classmate at Oberlin, she had slipped them back under his door and stopped talking to him.
He committed himself to journalism and activism. As he put it, "I saw it as my job to get white people to talk about race."
In 1994, a year after his influential "wigger" article, he self-published "Bomb the Suburbs" -- part memoir of a white man's life in hip-hop, part interviews with hip-hop figures, part treatise on race and social change. It sold an impressive 23,000 copies. The gangsta rapper Tupac Shakur declared it "the best book I read in prison."
Upski hitchhiked around the country, promoting the book, pushing his views on racial cohesion, further cementing his eccentric renown. "I thought white people would start listening to and liking black people," he said, but ultimately, he was discouraged.
He refocused. He would become a social-change agent, motivating whites to be activists. Last fall, he published "No More Prisons" and began the "Cool Rich Kids' Movement." He would coax cool rich kids to give money to the cause. He started the Active Element Foundation and, with an ally, a well-to-do white woman, also started a group, Reciprocity, that paid him a modest salary. This year, he began his college tour.
At Earlham, before a mostly white audience, Upski said: "The thing that drives me is getting to know people and making relationships across race and class, which doesn't happen so much in America. Some of the stuff I'm going to say is going to sound heavy, and you're going to say, 'Let me go smoke some weed and chill.' "
He bounced around the room, his manner that of the
motivational speaker. He said: "My goal today is to encourage
you to accept the best and worst things about yourself." He
talked about how they were too comfortable in this school, and
how he had been "saved" by transferring to a black school
after sixth grade. And then Rubberoom performed, and a lot of
people left and the remaining ones danced. Upski danced.
Chronicles of hip-hop
abound. Like The Source and XXL, they are mosty
white-owned. A brash and satiric black-owned hip-hop
magazine, Ego Trip, did not survive in print. A white
prophet of hip-hop, Upski, wrote a memoir, "Bomb the
Suburbs," and followed it up with "No More
Upski had brought along a copy of Stress, a small hip-hop magazine published by people of color. Upski told the students to read this, not the white-owned magazines.
He used to write for XXL, a fledgling magazine with a white owner and publisher. In 1997, the original black editor and black staff quit after being refused an ownership stake. There were innuendos of racism, but whether it was just business or race depended on the vantage point. Upski, however, swore never to work for XXL again.
After all, there were always ways for a smart white guy to make money.
Agonizing at the Monkey Academy
When the editor's job at XXL was offered to him last August, Elliott Wilson was put in a delicate spot. He was broke. In college, he accepted a flurry of credit cards and bought all the "fly" clothing. Now he owed $8,000.
He remembers thinking about how blacks needed to think more like whites. "We have a short expectancy in life," he said. "So we go for the quick buck. That's why kids sell drugs. That's why they rob. We don't feel we can be on a five-year plan to success."
The XXL job came with excellent pay -- low six figures. But talk of racial tension stained the place. He asked himself, he said, could blacks think he was selling out? First, he had to discuss it with the Ego Trip collective. He went over to the Monkey Academy.
Two rooms in a Chelsea basement, the Monkey Academy was a shrine to hip-hop. Roosting on a shelf was a "Talking Master P" doll ("Make 'em say uhhh") and a memento from Puff Daddy's 1998 birthday gala. Rap posters adorned the wall: Snoop Doggy Dogg, RZA, Jungle Brothers.
Ego Trip was five young men of color with ambitions of hip-hop entrepreneurship: Mr. Wilson, Sacha Jenkins, Jeff Mao, Gabriel Alvarez and Brent Rollins. They saw race as a depressive undercurrent to everything, and it was the focus of their scabrous humor. "We're always talking about the blacks and the whites," Mr. Wilson said. "That's the way me and my boys are."
The very name Monkey Academy reflected their saucy attitude. As Mr. Jenkins explained it: "Call me paranoid, but when I meet with white people, I feel that with their eyes they're calling me monkey. So why not wear that proudly? Everyone in hip-hop wants to use the N-word, so why not take it to the next level? Call us monkeys." They especially liked to trace their understanding of society to the "Planet of the Apes" movies, where the light-skinned orangutans controlled the dark gorillas.
Several years ago, the group published Ego Trip, which they saw as a magazine about race disguised as a hip-hop magazine. They invented a white owner, one Theodore Aloysius Bawno, who offered a message in each issue, blurting his bigoted views and lust for Angie Dickinson. His son, Galen, was a Princeton-educated liberal who professed common cause with blacks. But in truth, he was an unaware bigot, as Mr. Wilson says he feels so many young whites are.
So much of the hip-hop ruling class was white. As Mr. Wilson put it, Ego Trip wanted "to strike at all the black magazines that are white-owned and act as if they're black." It was a small irony that Ego Trip's seed money of $8,000 came from a white man, but at least he was a passive partner.
Though it gained a faithful following, Ego Trip stayed financially wobbly. No new investors came forth; the collective suspected the reluctance had to do with skin color. Ego Trip gasped and expired.
Now its founders scrambled with day jobs and worked on projects like "Ego Trip's Book of Rap Lists" and a companion album. Hip-hop Web sites were proliferating, and they hoped to start one, too. They said they wanted to hear the roar of money, on their terms.
"Black people create, but we don't reap the benefits," Mr. Wilson said. "We get punked and pimped. If we were white boys, we'd all be rich by now."
On that August day, he recalls, he sat on the couch, his emotions in an uproar. He had to wonder: was he now going to work for a true-life Ted Bawno? The others, he says, expressed a dim view of the XXL offer: "They were feeling I was pimping."
Not long before, he had been music editor of The Source. One duty was to rate new albums, on a scale of one to five "microphones." When he gave three microphones to "Corruption" by Corrupt, he says, the white publisher, David Mays, increased it to three and a half without telling him. When he confronted Mr. Mays, he concluded that the publisher did not respect him. Mr. Mays wouldn't give his side, but as Mr. Wilson tells it, he quit over half a microphone.
He felt strongly, he recalls, that he had to help himself. He no longer saw hip-hop as a great equalizer. "Who because of hip-hop now believes, 'I've seen the light, I'm going to save the blacks'?" he would say.
Sure, there was something positive in white kids' idolizing black rappers, but "what's going to happen when these white kids lose their little hip-hop jones and go work for Merrill Lynch?" he said.
What should he do? Months later, he remembers the confusion, the vectors of his life colliding. His throat tightened and he began to cry. He went to the bathroom of the Monkey Academy and composed himself. The message left hanging in the air from the others was, Do what you got to do.
As a black man, how many opportunities would come his way? He had this unslaked desire to prove his mettle. He took the job.
Tapping the Unconscious Biases
Upski went to the laundermat. Shaking in detergent, he talked about how he was a bundle of contradictions, subject to irrational racist phantasms for which he had no cogent defense. "I have patterns like every other white guy that I'm not very aware of that play out as racist," he admitted. He laughed at racist jokes. Walking down the street at night, he felt threatened if he saw a shabbily dressed black man. "I frequently feel I have more of a level of comfort and trust with white people," he said.
He talked differently to black friends ("Yo. . . That's wack. . . Peace, brother."). It infuriated his white girlfriend, Gita Drury. "I'll say to him, 'Do you know you're talking black now? Can you talk white, because that's what you are,' " she said. "I think it's patronizing." When he got on the phone, she could detect at once the caller's race. When he talked black, she would wave a sign at him: "Why are you talking like that?"
She saw this episodic behavior in other ways: "If we walk down the street and a black person walks by, he will give this nod, raise his chin a bit. He wouldn't do it with a white guy. I'll say, 'Oh, you have to prove to a black person that you're down.' "
Not long ago, Upski recalled, he spoke about race at a prominent college along with a black friend. He was paid twice as much as his friend. He spoke longer, but not twice as long. He never told his friend.
Sometimes, he said, he believed that black people were dumber than whites. Sometimes he felt the opposite. Now, as the washers ended their cycles, he hauled the wet clothes to the dryers. A stout black woman stood beside an empty cart. He asked if she was using it. She stared at him, bewildered. He asked again. Nothing.
Exasperated, he simply grabbed the cart and heaped it with his clothes.
Later on, he said: "When that happened, part of my gut reaction was, 'This is a black woman who has limited brain capacity, and it fits my stereotype of blacks having less cognitive intelligence.' "
Would a white woman have understood?
"It's dangerous for me to even say that," he said. "But that's what I thought."
Embarrassed by Rap's 'Babies'
The strip club was scattered with patrons with embalmed looks, solemnly quaffing their beverages. Elliott Wilson pulled up a stool beside a dancer. A fistful of dollars flapped from a rubber band curled around her wrist, the night's rewards.
Strip clubs, in particular this one in Queens, had a powerful hold on him. Though rap was his music, he said, he liked to unwind here rather than at a hip-hop club. There, everyone wanted something. Here, no one wanted anything but his money. "I'm not caught up in me and Puffy having each other's cell phone numbers," he said.
He had conflicted feelings about rap and rappers. "A lot of rappers rap about sex and violence, because people are interested in it," he said. "But it's art. It's poetry. If a rapper says, 'Kill your mother' in a song, it doesn't mean kill your mother. You can't take anything at face value." The real-life violence and arrests of rappers were something else. "Rappers are babies," he said. "They don't know how to balance their success and their street life. When I hear about Jay-Z this and Puffy that, I'm embarrassed to be part of the profession."
Mr. Wilson and his friend Gabe Alvarez shared an apartment in Clinton Hill, next to Fort Greene, a gentrifying neighborhood promoted by Spike Lee before he moved to the Upper East Side.
"Part of it's good and part isn't," Mr. Alvarez said. "You go a block over and there're the drug dealers."
"It's like the classic black neighborhood," Mr. Wilson said. "The liquor store, the bodega. I want good restaurants. I don't want to live in the 'hood. Who wants to live in the 'hood?" He wanted to move to Park Slope.
It was not his thing to go out of his way to patronize black businesses. It was fruitless, he said. He had seen that so much in hip-hop. "There's always a white man somewhere making money," he said. "You can't avoid the white man. My going to a black barber or something doesn't do anything."
Upski Meets Dog and Trife
Upski had gone to get his hair cut at the black-owned Freakin U Creations. He only went to black barbers, and part of his manifesto was to direct at least half his money to minority stores. Fort Greene afforded plenty of possibilities.
All in all, though, he found the neighborhood imperfect, already too gentrified. His girlfriend lived there, so he did. He had lived in a black neighborhood in Washington. He said he felt he belonged either in a rich white neighborhood, where he could persuade residents to integrate, or in the true 'hood, where he could organize. He mused about moving to East New York.
Upski chatted with one of the owners, Justice Cephas. Two young black men waited their turn. Mr. Cephas was a hip-hop promoter on the side and was working with their group. They were Dog and Trife.
Upski said, "Don't take anything off the top."
Dog studied Upski's pate and said, "What's there to take off?"
Upski laughed. He asked how they felt about whites' moving into the neighborhood.
"Five years ago, I would have beaten you up just for sitting in that barber chair," Dog told him.
"Oh," Upski said.
"But I've matured," Dog said.
Later, though, he talked about how he was still deeply bitter toward white people. No white person had ever done anything positive for him, he said. As he remarked of whites: "I've never been with you. Why would I want to be with you now?"
Trife added, "If you're not my people now, you're not my people down the line."
Dog and Trife had told Upski about their group, Wanted and Respected. Trife's older brother had started a record label, Trife-Life Records, and they were working on its first album. They hoped to sell it on the street, create some buzz. All the while, Trife said later, he was thinking, "What is this white guy doing in this barbershop?"
Upski smiled. These young men, he said, reminded him of the black friends he used to run with in Chicago. If he were younger, he mused, he might want to run with them.
The Beatles Parallax
Inside Elliott Wilson's XXL cubicle was a computer, a stereo and a table strewn with rap albums. The music was on -- loud.
His eyes scanned the screen -- copy for the next issue. He fiddled with it. "I'm adding curse words," he said. "Putting in ain'ts. Making it more hip-hop."
The publisher, Dennis Page, came in with his beneficent smile. "Hey, man, we doing O.K.?"
Mr. Page peeked over his shoulder at the screen. He nodded: "That's dope."
They went on like that, bantering.
Mr. Wilson called his boss D.P.G. -- Dennis Page Gangsta, after Snoop Doggy Dogg's crew, the Dogg Pound Gangstas. Mr. Wilson had given D.P.G. an inscribed copy of "Ego Trip's Book of Rap Lists." He wrote, "I don't care what people say, I know your favorite color is green."
It was how he felt about the relationship. They were both there for the money, he said.
Dennis Page was 46. He had the black walk, the black talk. His father had run a liquor store in Trenton, and Mr. Page had hung around with black kids and absorbed their ways. Now, he says, he has no real black friends. He admits he's been called a wigger. "I feel stigmatized by black people in hip-hop who feel I'm exploiting them," he said. "I don't feel I'm exploiting. It's a business. The record companies are white-owned. But I feel I take more heat. Certain black people feel that white people shouldn't even buy hip-hop albums, no less write about it. I'm not saying a black man can't buy a Beatles record."
XXL was just going monthly, and its circulation, which it gave as 175,000, was still far below the leading magazines' -- Vibe sold more than 700,000 copies, The Source 425,000. XXL had been heavily political, clearly aimed at blacks. To build up the white audience, Mr. Page and Mr. Wilson agreed to tone it down, focus it almost entirely on the music.
"My magazine isn't some white-boy magazine, though," Mr. Wilson said. "It's black, too. I'm not sacrificing what XXL stands for." Even so, he added, "it can't be totally black if a white man is signing the check."
'I Preach to Mess Up'
Tuesday dawned muggy. It started badly and got worse. Upski was addressing about 250 students at Evergreen College in Olympia, Wash. Maybe 10 weren't white.
He had gathered a panel of half a dozen students. One, Evelyn Aako, was black. Introducing her, he said: "I don't know her very well, but she's black. And she's going to talk about issues of being black on campus."
Ms. Aako gave him an arch look. "That was very weird," she recalled thinking. "Like I was a little dark object."
As Upski began talking, the white audience got defensive. One student said: "Why do we have to talk about race? Why can't we talk about how we're alike?"
Ms. Aako was getting disgusted. Finally she told Upski: "I've been sitting here with an uncomfortable feeling in my stomach about how you introduced me. I felt tokenized and on display. This follows a tradition where black people serve as entertainment for white people. That's not what I do."
Upski said: "I screwed up. But what can we do? The world is screwed up."
Some white students were looking irritated. One said: "Can't we hear Upski talk? We can talk about race later."
A black student said: "What do you mean later? We never talk about race."
Some whites left. Virtually all the students of color followed. Before leaving, Ms. Aako said, "It's not my job to educate you."
Later, Upski sounded no less confident of his ability to stimulate change. But perhaps, he said, he needed to refine his approach.
"I think the main thing that keeps white people from growing is they're afraid to look bad," he said. "So I preach to mess up. One of my blind spots at Evergreen was that Evelyn wasn't going to trust me, that black people and white people, we're still at war."
Increasingly, he said, he was questioning his own evolution. Here he was intent on helping blacks, and spending most of his time in white culture. He had had a string of black girlfriends, but now he was with a white woman. A few years ago, probably two-thirds of his friends were black and Latino. Now it had flip-flopped.
Hip-hop itself had moved away from political and racial talk and for the most part sold excess and riches, women and violence. So much of hip-hop, he said, was self-denigrating, imitative and shallow. It was candy.
"One of the things I have the least respect for about parts of black culture," he said, "is there's so much pain and insecurity that it gets medicated by aping the worst aspects of white culture."
He talked about how so many of his old black and Latino graffiti friends hadn't survived hip-hop too well. One got locked up for firebombing a car. Another fell from a fire escape while trying to rob an apartment. He is now a paraplegic, drinking away his life, Upski said.
And yet, Upski had to admit, he was cruising along. His girlfriend, Ms. Drury, had inherited money, though they lived modestly. He didn't earn a lot, but he didn't worry. Until recently, he never took cabs and rarely ate out; he called it flaunting privilege. But now he was traveling more in white circles where everyone took cabs and ate out. So he did, too. And, he acknowledged, he liked it.
"The part of Billy that wanted to be black for a good part of his youth, that's fading," Ms. Drury said. "One of the issues in our relationship is he's a chameleon. The thing with Billy, he wants to be liked."
He had always cared so much about how he looked through black eyes, he said. Now his success depended on how he looked through white eyes. He had always dressed poorly and now he owned three suits. Where was he going? he wondered. As you got older, holding onto your hip-hop values seemed a lot harder if you were white.
Traps and Trappings of Success
Elliott Wilson climbed the stairs to the basketball court. The old guys were already there. The doctor had told him he had high blood pressure, a real slap in the face. "I've got the black man's disease," he joked.
Who knew the factors, but he had never eaten properly. He was also feeling the pressure of his job, he said. A friend who had been editor of The Source said the same thing had happened to him.
His doctor put him on medication, urged exercise. So he had begun playing full-court basketball three mornings a week. There was an early crowd of young guys, but Mr. Wilson wasn't ready for them. He played with a bunch of white guys, some in their 50's and 60's, and one black guy in his 70's. He hit some baskets and missed some. He changed and headed for XXL.
He had now edited four issues. The first one, with DMX on the cover, had outsold any previous issue. He felt he was making a mark, he said. He had his disputes with Dennis Page, but they got along. His Ego Trip comrades felt proud of him.
He was making such good money, more than three times what Upski made, but somehow, he said, that wasn't the point. What he really wanted was to "take The Source out in a year or two," then expand the reaches of Ego Trip. Still, there were always seeds of self-doubt.
"Do I feel secure?" he said. "No. Because I'm black and I have bad credit. Having bad credit in this country is like being a convict. You don't have a prosperity mind-set when you're a person of color. You have something, you always feel someone is going to take it. You're always on edge, wondering what next."
'I Just Want the Money'
Dog twirled the dials and gave Trife the signal to start. In the tiny apartment, Dog and Trife and Sinbo and Po were rehearsing for their album, the one they hoped might be destiny's next chosen one.
Scrizz, Trife's brother and the C.E.O. of Trife-Life Records, was listening like a jittery father. With no product yet, Trife-Life was not a paying job for him. His background, like that of the others, was drugs and crime. At the moment, he was out on bail while fighting an assault charge.
Wanted and Respected started in on its song "All the Time." Golden bars of light streaked through the windows. Scrizz tapped his foot. He, too, had a got-to-happen mentality. He didn't much care who bought the album, white or black, but he knew where the money was. "I just want them to eat it up," he said. "I just want the money."
It came down to that. A group of young black guys in Brooklyn rhyming their lives, betting on a brighter tomorrow sponsored by white kids' money.
Dog turned up the music. They cleared their throats and kept rapping.