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.
 
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  | 
 
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."
 
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  | 
 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."
 
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  | 
 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 Prisons." 
 MORE PHOTOS 
  | 
 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.?"
 "Yeah."
 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. 
 
  | About This Series | 
  | 
Two generations after the end of legal discrimination, race still ignites
political debates -- over Civil War flags, for example, or police profiling.
But the wider public discussion of race relations seems muted by a
full-employment economy and by a sense, particularly among many whites,
that the time of large social remedies is past. Race relations are being
defined less by political action than by daily experience, in schools, in
sports arenas, in pop culture and at worship, and especially in the
workplace. These encounters -- race relations in the most literal, everyday
sense -- make up this series of reports, the outcome of a yearlong
examination by a team of Times reporters.
 | 
 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.
.
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