Damon Dash Resurrected

Cast out of Jay-Z's kingdom, a notorious hip-hop mogul takes a kinder, gentler, hipper approach to reinvention

On a recent muggy evening, veteran Houston rapper Bun B performed in the basement of a luxe Tribeca gallery. It was a dark, crude space, packed to the gills, as if a Bushwick loft party had burrowed up through Manhattan topsoil.

Empty Budweiser cans collected in corners, smoke clogged the air, and condensation gave the walls the slick glisten of a slug's belly. "This is the hottest place in the world," Bun marveled, a sheen of sweat reflecting off his bald head. His live backing band eased into the opening bars of "International Players Anthem," and the crowd voiced approval. Among that congregation was Damon Dash, grinning, giving out hugs, and chortling with laughter, back in the thick of things.

Dash's new gallery, DD172 (his initials and the Duane Street address), is a different world from the dank catacombs beneath. The hardwood timbers are spotless; the white walls of the ground-level exhibition area soar upward into the airy office space where he now works. Six years have passed since the splintering of Roc-a-Fella Records, the hip-hop label Dash and Jay-Z built into a sprawling entertainment empire. Jay long ago ascended to a rarefied plateau of celebrity where the absurd is normal: He fraternizes with Russian billionaires, taunts Noel Gallagher at Glastonbury, and makes sweet love to Beyoncé on a mattress stuffed with unicorn hair. Dame has not been so fortunate: One by one, his flotilla of business ventures—in music, fashion, sports promotion, publishing, and film—have sunk. Following a much-publicized fall-out with his former cohort, his reputation as a cagey entrepreneur was tarnished, his fortune stripped clean, his marriage to fashion designer Rachel Roy torn asunder. And he is happier than ever before.

A new man, now surrounded by fellow artists, not Scarface posters
Raquel M. Horn
A new man, now surrounded by fellow artists, not Scarface posters
In the studio, with Sienna Miller (!)
Raquel M. Horn
In the studio, with Sienna Miller (!)
With Jim Jones during the 
BlakRoc sessions
Jonah Schwartz
With Jim Jones during the BlakRoc sessions
With daughter Tallulah
Raquel M. Horn
With daughter Tallulah

Morning sunlight spills into Dash's office, the man himself splayed across a furry white couch beneath a large, feathered Ojibwa dreamcatcher. He wears a fuchsia T-shirt with diagonal yellow stripes, jeans, and tortoise-rimmed glasses that, when coupled with the flecks of gray in his beard, give him a "rad dad" look. He shares the space with a pair of women in their early 20s who have ascended, in the manner of a metastasizing start-up, from assistants to heads of divisions. The woman who presides over the music wing is also a singer; the one running the magazine America Nu, Dash explains, "loves taking photos and doing artistic things." He says he prefers working with women because they're harder to yell at.

In a few hours, the compound will pulse with creative energy: Such up-and-coming rappers as Curren$y and Stalley will record in the music studios, while a video production team called Creative Control works from editing bays. Enjoying the morning's relative calm, Dash wanders from his office into a wider area where a few people quietly tap away at laptops. "I'm not surrounded by posters of guns and Scarface here," he notes. There's no sign of Tony Montana, true, but the gallery walls are covered with stylized portraits of marked militants wielding Kalashnikovs. This is the evolution of Dame Dash.

Born and raised in Harlem, Dame seemed to have hustling in his bloodstream. His mother sold clothing out of their apartment. His cousin, Darien Dash, was the first African-American to take a dot-com public. Actress Stacey Dash is a cousin. Discipline problems kept Damon bouncing around private schools like Isaac Newton and South Kent on scholarship, but he eventually earned his GED, and began promoting parties and managing musicians in the early '90s. "He was an undeniable ball of energy," says Clark Kent, the Brooklyn DJ and producer who worked with Dame at Atlantic Records and first introduced him to Jay-Z in 1994. "I saw that he had a relentless approach to having his way. He approached everything with an independent spirit that makes people either get down or lay down."

Roc-a-Fella became a record label that same year, a partnership between Jay, Dash, and Kareem that quickly led to a pressing and distribution deal with Priority Records; after achieving critical acclaim and moderate commercial success with Jay-Z's 1996 full-length debut, Reasonable Doubt, the Roc-a-Fella trio retained their independence and signed a co-venture deal with Def Jam for a reported $1.5 million in expansion capital the following year. "It wasn't like it was built to be this record label," says Kent. "Everything they did was like homeboys. The premise was to make one album, but it was too good and too easy."

Money started pouring in when Jay-Z's third album, 1998's Vol. 2 . . . Hard Knock Life, sprinted to the top of the charts and sold five million copies domestically. The LP's club-friendly combination of dexterous lyrics and sparse, spacey beats made Jay a star, and his reflected glow was enough to help Memphis Bleek's Coming of Age (1999) and Beanie Sigel's The Truth (2000) become gold-certified debuts. Roc-a-Fella was further legitimized as more than just a one-man show with subsequent signings: At full strength, the roster also included Kanye West, Cam'ron, Juelz Santana, State Property, M.O.P., and, strangely, Samantha Ronson. Other labels were crossing the Mason-Dixon Line in search of fresh talent, but Roc remained an obelisk of street-oriented East Coast lyricism and soulful-yet-punchy production in the face of the rising Southern tide.

Dash was a star himself, challenging Diddy as the most visible hip-hop executive. He splashed champagne on girls in videos, dated the r&b singer Aaliyah, and reveled in his reputation as a pugnacious asshole in the boardroom. He now regards the Roc-a-Fella heyday with some regret: "I didn't really understand the ramifications of being so influential, of saying things that could potentially be negative," he says. "At the time, it was about getting money at any cost and talking about buying nice things that most people couldn't afford. I think it put a very superficial mentality into the world. If you're rapping about doing criminal things, the majority of your fans are criminals or fans of criminals." Whatever the merits of his social critique, Roc artists talked about it because they lived it: Sigel, for example, beat an attempted-murder rap in 2004 (although he served time on separate federal weapons charges), while Peedi Crakk did several stints in prison, most recently until April of this year.

If Roc-a-Fella really was injecting malevolent thoughts into the soft skulls of the impressionable, that brainwashing mercifully ended when the company was cleaved apart in 2004. Tension had been mounting for more than a year, starting when Dash appointed Cam'ron, a crony from Harlem, one of the label's vice presidents, while Jay-Z was vacationing in the Mediterranean. Eventually, Jay decided to sever business ties with his fellow founders; their stake in the company was sold back to Island Def Jam for a reported $10 million, while controlling interests in the remaining clothing, film, and alcohol ventures were sliced up. Jay signed a three-year contract to become president and CEO of Def Jam—a position he would leave in 2008 for Live Nation. He offered the rights to the name "Roc-a-Fella" to Dash and Biggs in exchange for the recording masters to Reasonable Doubt, but the pair wouldn't make the deal. "We all earned those masters," Dash says.

This turn of events remains bewildering. "The people that I was helping, once they realized their dreams, they did what a criminal would do," Dash continues. "They stabbed you in the back. Think about the frustration of building a brand for years that should be taking care of your family, and then the person that was the closest to you saying, 'Nah, you can't have no parts of it,' and flushing it."

It was the end of an era, both for East Coast rap and for a label whose artists and executives were once so close that they ate Sunday dinners with Jay-Z's family. Artists were divvied up, forced to pick sides. "I thought it was fucked up," says Leslie "Freeway" Pridgeon, a Philadelphia rapper who released his debut album on Roc-a-Fella in 2003. "I missed the whole family structure that we had: Dame, Jay, Biggs. It was more than just music, like we're riding regardless." The road had forked.

In 2006, Dash boasted to New York magazine that he was worth approximately $50 million. He and his wife owned a loft in Tribeca and a house in Beverly Hills. There was a personal chef and a $400,000 Maybach 62 with a driver. His closet housed 300 pairs of sneakers, with another 1,000 in storage. But Dash was a benevolent overlord: He wore a fresh T-shirt and pair of socks daily, then donated the once-worn items to charity. Whatever acrimony existed from the destruction of Roc-a-Fella was buried beneath heaps of money and a slew of entrepreneurial projects, including the Damon Dash Music Group, the Rachel Roy Designer Collection, Pro-Keds sneakers, Armandale vodka, America magazine, BlockSavvy Technology, an Apprentice-esque BET reality show called Ultimate Hustler, and excursions into the cinematic world.

But these new endeavors failed to benefit from the platinum touch Dash exhibited at Roc-a-Fella. A career as a boxing promoter—he partnered with former HBO executive Lou DiBella to form Dash-DiBella Boxing—fizzled. Despite a claim that his stable of fighters "all like to knock niggas the fuck out," none rose to champion ranks. Punches landed also at America, a glossy men's publication that folded shortly after the editor-in-chief filed a police report alleging Dash assaulted him. And although Dash had portrayed himself as an owner of Pro-Keds, the deal he struck in 2004 was only to license the name; he agreed to pay a monthly premium in order to build up the brand, with the stipulation that he would split the profits if the company later sold above its original value. Only problem: Pro-Keds was part of Stride-Rite, a publicly owned company. He was paying to promote a company in which he had no equity. "Bad deal on Dame Dash's part," Dash says now. "That's over."

The poor investments added up. By 2008, Dash owed New York State $2 million in taxes and faced lawsuits from lawyers and landlords. A bank began foreclosure proceedings on his Manhattan property; a judge ordered the seizure of his Chevy Tahoe. "No money, mo' problems" crowed the Daily News. Dash cut his losses, selling half his stake in the Rachel Roy Designer Collection to Jones Apparel Group. He claims the transaction as a victory, even if financially pyrrhic: "In a recession, I sold a company that had nothing to do with something I was perceived as knowing how to do," he says. "It's not about being famous, it's not about being rich. It's about having taste and style, and I was able to penetrate that, getting into the same circle as Anna Wintour, André Leon Talley. Instead of being best-dressed in Vibe, I was best-dressed in Vanity Fair." Still, as his business endeavors faltered, so did his marriage. In March 2009, his wife of four years—and mother of two of his children—filed for divorce. Dash won't discuss the current state of their relationship, but still refers to her as "my wife."

There's no shortage of people who've made and squandered fortunes in the entertainment world. But Dash's crash was magnified by the success—totally unprecedented, really—that Jay-Z has enjoyed. It would have been acceptable if the rapper had reached an artistic peak after the Roc-a-Fella break-up, but his most notable accomplishments came in Dash's supposed realm of expertise: marketing, branding, endorsements, and a spiderweb of business deals, including a small stake of ownership in the New Jersey Nets. In 2006, "Lost One," an early Jay single after his "retirement" hiatus, included what appeared to be a line directed at Dash: "I heard motherfuckers sayin' they made Hov/Made Hov say, 'OK, so make another Hov'/Niggas wasn't playin' they day role/So we parted ways like Ben and J-Lo." Both the winner and the loser were clear.

Where Roc-a-Fella was a stronghold for the baggy-jeans-and-dangling-medallion set, events at DD172 attract a downtown crowd where guys in gingham shirts, thick glasses, and colorful sneakers mingle with attractive, post-neo-soul girls. At a recent opening, a group of attendees sipped caipirinhas made with coconut water and inspected those menacing pictures of gun-toting extremists. It was entry-level stuff, but fun. For Dash, this scene is ideal: "When I look at a hip-hop mogul that was relevant 10 years ago, they should be doing exactly what I'm doing," he says. "It should be something intelligent and renaissance." He uses words like "renaissance" frequently—also "moral fabric" and "quality of life" and "evolution." There's a classist strain of pride in his discussion of transitioning from the hip-hop world to that of fashion and culture, but his fabled obnoxiousness has been tempered with some humility. Still, midway through being interviewed, he stops mid-sentence to gripe: "Know why I'm tight right now?" he asks the room. "Nobody taping me." Someone grabs a digital video camera and starts filming.

Dash has begun working with a new collective of hip-hop artists, and he naturally draws comparisons to the formative days of Roc-a-Fella. But in a case of dramatic reverse-engineering, one of the notable proponents of glittery mainstream rap has been reborn as a purist backpacker. "I wasn't aware of this beautiful movement of artists that stick together, that don't rap about negative things," he says. "They have swag, style, and they're with me because they love the fact that I preserve their independence. I'm not exposed with them. I didn't have to give them any money to get down with me." One project, titled 24-Hour Karate School, brought together Ski-Beatz, a producer who created much of Jay-Z's Reasonable Doubt, and underground artists like Mos Def, Jean Grae, and the Cool Kids. The BlakRok LP put indie rockers the Black Keys in the studio with Jim Jones and RZA. After years of rolling to shows 20-deep in expectation of brawls, Dash expresses awe that Curren$y, a New Orleans rapper once affiliated with Lil Wayne, tours without an entourage.

Likewise, the troupe of young artists who records in DD172 was surprised to encounter the current incarnation of Dash. "I grew up seeing Dame pouring bottles on models and doing dances and being very arrogant," says Stalley, a bearded rapper from Ohio. "But he's nothing like that. He's very down-to-earth, very humble. I think the other way that he did it wasn't as much fun as it is now."

Last week, Curren$y released his LP Pilot Talk on Roc-a-Fella Records, joining Kanye West and Jadakiss as the only artists to put out albums on the label since 2007. It was Dash who put together the pressing and distribution deal with Def Jam; the familiar Roc logo is both imprinted on Curren$y's album and hangs from a chain around his neck, suggesting the label may be in mid-resurrection. Dash, veteran promoter that he is, effuses praise for his new charge: "He'll be bigger than anyone I've ever worked with," he says with conviction undiminished by the statement's unlikelihood. To him, things are always possible: "A lot of things I'm saying now will not resonate to the average individual for five years," he says. "So five years before it happens, I sound crazy."

Battered but far from broken, Dash remains a feverish salesman, an entrepreneur with a proud independent streak, and a self-proclaimed visionary. One thing he's never been is a musician. He's never rapped, never sung, never produced the tracks his artists performed over. Now, he rises from the couch in his office to lift up a turquoise guitar. He sits back down, rests the instrument on his knee, and strums a simple melody. It's shaky, but he stumbles on. "I can do this all day," he says happily. "I've been playing the same exact song for six months, and nobody cares."

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