In 1982, the year hip-hop began to make it seem like the ’60s might finally be over, oversized radios were pumping the utopian futurism of Afrika Bambaataa’s “Planet Rock” and the urban neorealism of Grandmaster Flash and the Furious Five’s “The Message.” Downtown darling Jean-Michel Basquiat, known on the New York streets as SAMO, painted a memorial to Charlie Parker that read: most young kings get thier head cut off. The current owner of that painting is a relatively new player in the art-world bull market named Shawn Carter, known around the world as Jay-Z.

Ten years ago, Jay-Z made his debut with the critically acclaimed album Reasonable Doubt, a portrait of a Bedford-Stuyvesant drug dealer on the verge of his biggest break. Impossibly cool on the surface, his hustler persona was unmistakably desperate at the core. The album was powerfully encapsulated by one of its track titles–a credo that doubled as a refrain, as simple as it was haunting: “Can I live?”

The question seemed particularly timely. Within a year of Reasonable Doubt‘s release, two rap kings met bloody ends: Tupac Shakur was murdered in Las Vegas, and Shakur’s rival and Jay-Z’s close friend The Notorious B.I.G. was gunned down in Los Angeles. But hip-hop’s restless competitive ethos abhors a vacuum at the top, so Jay-Z stepped up and seized the rap crown. During his reign, he underwent a transformation from street hustler to high-end brand name, helping found what advertisers now call the “urban aspirational” market.

Three years ago, having reached what he thought was the limit of his rap powers, he retired on top, like Michael Jordan after his Jazz-killing jumper, with a fine, revealing record, The Black Album. He was burying his rap persona, or at least he said he was. In the summer of 2005, Carter’s 18-year-old nephew was killed in an auto accident, driving the Chrysler 300 that had been a graduation present. Who can say how much death has figured in Jay-Z’s rise and return? Perhaps living means never quitting.

In 2004 he was named CEO of rap’s most storied label, Def Jam, the same one he helped rebuild as a hungry artist. (The deal included the chance to repossess his master recordings, a rare contractual clause rife with racial symbolism.) A tastemaker nonpareil, he started wearing button-downs and Evisu jeans, and urbanwear felt the shock waves. When, having learned of Roederer Cristal’s distaste for its urban customers, he stopped drinking the $200 bottles of champagne, thousands joined his boycott. He is the most famous co-owner of the New Jersey Nets and has supported a controversial proposal to move the team to his beloved Brooklyn, a project that has already unleashed rampant real estate speculation.

It wasn’t much of a retirement. Before long he was guest-starring on countless recordings and launching high-profile shows and tours. Not even a growing beef with disaffected Roc-A-Fella rapper Cam’ron and his crewmate Jim Jones could slow Jay-Z’s hustle. His hobnobbing with champagniers in France or with Gwyneth and Chris in London, as well as requisite outings with his glamorous girlfriend Beyoncé Knowles, became gossip-column fodder. As Brooklyn’s answer to Bono, he held court with Kofi Annan and Nelson Mandela and traveled to Tanzania and Nigeria to shoot an MTV documentary on the global water crisis. He could have rested on such clout. But he decided he wasn’t ready not to risk his neck anymore.

In November he roared out of rap retirement with Kingdom Come. The record is strangely disengaged and absolutely disposable. But its release has occasioned a dazzling display of brand leveraging. In a photo spread for a fawning GQ Man of the Year cover story, Jay-Z threw up a Black Power fist while dressed in a Club Monaco cardigan, a Purple Label button-down and his own Rocawear sweats. The man who used to show off a Che Guevara shirt, his ice chain covering the red star on that famous beret, had repackaged hip-hop’s rebellion into a symbol of the postmulticulturalist good life.

As Budweiser Select’s “co-brand director,” he appeared in a commercial with NASCAR drivers Danica Patrick and Dale Earnhardt Jr. to announce Kingdom Come‘s release date during Monday Night Football and the National League championship series. (By comparison, former mentor Sean “P. Diddy” Combs launched his new album with a Burger King-sponsored video on YouTube.) On an HP commercial, Jay-Z outlined a typical executive day with his usual bravado, commenting on an online chess move he had just made: “This game is over. I wonder if he knows.”

Jay-Z himself fueled the engines of this monopoly mediascape. When the album leaked onto the Internet, he countered with free previews of Kingdom Come on 220 Clear Channel stations. Then he got in the charter jet for a twenty-four-hour, seven-city tour blitz. Captured online and on TV almost in real time, this act of twenty-first-century omnipresence seemed to spin his hilarious evangelical-baiting, God-complex nickname, J-Hova, into something else. The world was his witness.

On November 28, near the end of another year of plunging record sales, Jay-Z made good on his claim to being “hip-hop’s savior.” Kingdom Come became his ninth No. 1 album, tying him with the Rolling Stones in chart toppers and making him the most successful rapper of all time. Its first-week sales of 680,000 copies made it one of the biggest pop blockbusters of the year. By any measure, Jay-Z has accomplished his goal: He is the black face of the new establishment.

But wasn’t hip-hop supposed to be the new counterculture? It certainly felt that way in the late 1970s and early ’80s, when the movement was led by politically abandoned youths of color like DJ Kool Herc, Afrika Bambaataa and Grandmaster Flash. The culture’s first institution, Bambaataa’s Universal Zulu Nation, was inspired by black radical ideologies and presented itself partly as an alternative to gang warfare.

While pundits dismissed the culture as a youth fad, the ecstatic encounter between hip-hop’s adherents and downtown’s avant-garde in the morning of Reagan’s America produced genuine excitement. Young hip-hop heads found open doors to formerly exclusive circles. White urban hipsters saw poor youths of color as bleeding-edge prophets of social rebellion and aesthetic iconoclasm, raw voices of truth and freedom. (Such ferment had not been felt since John Sinclair and the White Panthers were inspired by free jazz and the Black Panthers to talk dope, rock and roll, and fucking in the streets.)

Of course, first-generation rappers had always been more likely to talk champagne, caviar and bubble baths–to drop brand names rather than reality raps. In 1982, while “The Message” captivated downtowners, uptown DJs were snapping the records over their knees and throwing them away. Many hip-hop heads didn’t have any romanticized notions about living close to the edge.

In the mid-’80s, hip-hop’s first crossover fired the imaginations of kids from Coxsackie to Cairo. As they grew older, many of them came to believe that diversity could triumph over American monoculturalism. By the end of the decade, they were moving both musically and politically with confidence and urgency, determined to blast away rock orthodoxy and racism with word, sound and style.

Then they won. Unlike Parker and his fellow beboppers, who often felt like exiles in their own country, hip-hop entrepreneurs like Russell Simmons, Combs and, later, Carter rode a wave of demand and brought hip-hop into the mainstream. When rock counterculture became the dominant pop culture, most musicians or managers didn’t become brand stars. But in the postindustrial economy, Simmons, Combs and Carter embodied–in the clothes they wore, the consumer goods they endorsed, even the political causes they championed–a hip-hop lifestyle.

Simmons and Combs grew up in black inner-ring suburbs enamored with the style of the kids from the other side of the tracks, but Carter was one of those kids. He came from the Marcy Houses, the projects in Bedford-Stuyvesant once overtaken by drug gangs. As Jay-Z, he wrote songs about cocaine, but these were not tales of rock-star high times, à la J.J. Cale and Eric Clapton. They were often harrowing stories of wise-beyond-their-years teen dealers who had to “learn to live with regrets.” He and fellow New York rappers Nas and The Notorious B.I.G. borrowed from West Coast “gangsta rap” the figure of the hustler, but they focused on the low end of the hierarchy, on the kid who could be found “grinding” on the corner day to day–always restless, always endangered, hoping to outwit cops, murderous rivals and turncoat allies to rise above the scrum. Release came in classically American displays of conspicuous consumption–bawdy, garish, often sexist–the line connecting music-video bling to Tony Soprano’s bada-bing.

By the time Jay-Z released Reasonable Doubt in 1996, President Clinton had been elected to a second term, and his promises of post-LA riot change had given way to legislation that brought massive prison growth, the “end of welfare as we know it,” the rise of workfare and corporate globalization. It’s no coincidence that “Politics as Usual,” the title of one track, was New York City slang for the drug game. On “Where I’m From,” off In My Lifetime (1997), he rapped, “Government? Fuck government. Niggas politic themselves.”

Jay-Z met the economic expansion of the 1990s–unleashed by corporate consolidation and free-market globalization–by making his pop slicker, dabbling in world-pop sounds and creating bigger, more seductive fantasies of success. (About this time, a group of rappers from the housing projects of New Orleans called the Cash Money Millionaires introduced the word “bling” into the lexicon.) Yet he also used civil rights imagery to buttress his self-mythology. No longer claiming to represent merely the Marcy Houses but also “the seat where Rosa Parks sat, where Malcolm X was shot, where Martin Luther was popped,” he even called himself “the soul of Mumia.” With these comparisons, Jay-Z not only flattered hip-hop’s sense of itself as an insurgent culture but claimed–with typical braggadocio–a place for himself alongside icons of the black freedom struggle. Clearly there was much more behind the game face he was showing.

Corporate media’s massive economies of scale favor a drastically limited scope of rap archetypes that, not coincidentally, traffic primarily in stereotypes of black sexuality and criminality. Labels make fewer signings, so there are fewer “types” to represent. Furthermore, those signings tend to fill old boxes: the party girl in furs and stiletto heels, the gunslinger at odds with rivals and cops, the crack dealer on the corner. Jay-Z admitted as much on The Black Album, a record that led one of his shrewdest observers, Elizabeth Mendez Berry, to call him a “confidence artist.” But he claimed simply to be giving the people what they wanted: “I’ve dumbed down for my audience and doubled my dollars,” he said on “Moment of Clarity.” “They criticize me for it, yet they all yell, ‘Holla!'”

So Kingdom Come finds Jay-Z struggling to figure out, as he asked on The Black Album, what more he can say. Gone are the drug dealer stories. The hustler is no longer on the corner. In a dedication to his old jailed friends, beautifully sung by John Legend, called “Do U Wanna Ride?” the mention of coke is product placement for the cola, not just the illegal product cut and cooked with baking soda.

On the record’s emotional set piece, “Lost One,” Jay-Z’s trademark flow fails him, and he stumbles badly. When he disses and dissects his former Roc-A-Fella partners in the first verse, he rides the rhythm easily. But over the next two verses–about problems in his relationship with Beyoncé and about his deceased nephew–he sounds tongue-tied. It’s a clue that this restless hustler is no good at endings.

Jay-Z sounds most comfortable rapping over bombastic tracks by Just Blaze, a young New Jersey producer with a gift for taking familiar beats and classic hip-hop breaks and flipping them into arena-sized anthems. But hip-hop’s most artistically expressive tension comes from the underdog’s striving to become top dog. As a cocky teen, Def Jam’s first star, LL Cool J, once said, “Even when I’m bragging, I’m being sincere.” But CEO Jay-Z is now a 37-year-old, straining for relevance with a new refrain, “30 is the new 20.” Heard over a bench-warmer beat by the 41-year-old Dr. Dre on “30 Something,” it’s the least convincing line he’s ever uttered. When he boasts about collecting passport stamps, working stock portfolios and buying Birkin bags for Beyoncé, he is no longer endearing. The man who once apotheosized “urban aspiration” is beyond reach.

If Jay-Z’s art is no longer influential, his influence on the art is more pervasive than ever. His bold signings at Def Jam–from teen idol Rihanna to lyrical hero Ghostface Killah to sophisticated soulster Ne-Yo–might prove that the hip-hop market encompasses a wider demographic than anyone else in the industry imagines. And as Jay-Z has moved from the corner to the boardroom, a significant group of new generation artists–including his Def Jam signings Rick Ross and Young Jeezy–continue to mine the territory he opened with Reasonable Doubt, a genre many now refer to as “crack rap.” The second-biggest hip-hop release this year was by Atlanta’s T.I., a former drug dealer turned movie idol who has reworked Jay-Z’s late-’90s mix of crack and bling into platinum status. One of the most acclaimed releases this winter was by a Virginia-based pair of ex-dealers called the Clipse, whose 2002 hit “Grindin'” ushered in crack rap’s return.

Unlike the business metaphors (“Rap Game/Crack Game” was one of Jay-Z’s most popular songs) and Scarface-like heights and depths of the crack rap of the ’90s bubble economy, most narratives now start with kitchen-scale claustrophobia. Lyrics fuss over the details of “the work”– the drop, the baking, the setup, the sale, the re-up–because everything after that is idleness and fear and justification. Backed by sci-fi textures, the Clipse offer dystopian futurism like writer Richard Morgan, while Young Jeezy’s lushly orchestrated tracks infuse its tiny world with romantic grandeur. It’s the sound of lowered expectations straining to be shockingly new, or simply noble.

Crack rap’s resurgence is not a case of, to use a rap cliché, “street journalism.” In many cities, heroin tops have supplanted crack rocks as the scourge of choice. And although there has been an alarming rise in urban gun homicides across the country, some evidence suggests that the numbers do not signal a repeat of the ’80s drug wars. Hip-hop journalist Kris Ex has written that crack rap is now primarily a matter of “style and design.” This music, which is being pushed by global corporate conglomerates, sells a myth of street life that makes crack production a metaphor for the new economy.

Amid war, post-Katrina unrest and, especially, expanding joblessness, the small-time hustlers of crack rap provide a strange kind of comfort. In a “free-agent nation” where fortysomethings routinely find themselves pink-slip obsolescent and twentysomethings are encouraged to prepare themselves for an insecure occupational future by becoming their own brands, perhaps crack rappers–whose desire for the good life is matched by the insecure certainty of the kitchen-and-corner struggle–have become the new countercultural heroes. Of course, this counterculture too comes with its illusions. Kris Ex reminds us of “the thirteen-year-old spotter caught up in a turf war, the five-year-old girl that takes a stray bullet…. Every real crack rock that is sold, is sold to a real person.” The tragedies of crack rap are the stories never told, the fallen bodies never counted.

When Basquiat died, his friend Keith Haring painted a memorial featuring a pyramid-shaped heap of tumbled crowns, a graveyard of kings. For now, Jay-Z has avoided this fate. But if he can’t be trusted when he says that “30 is the new 20,” it may be because we know his neck will still be well protected when he turns 40 in a few years.