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Roc of Ages: Dame Dash's Second Chance at a Second Act

Damon Dash is 44-years-old and if you pay attention, you can see that he is playing a character he is presenting to the world. Damon Dash starring in 'The Life of Damon Dash.'

Illustration by Rob Dobi

Damon Dash is sitting in the loft space that he calls his own on the Lower East Side of Manhattan. It is named Poppington, and bills itself as an art gallery of sorts, although there is not much art on display. Well, except for maybe Dash himself, whose mere act of existence has at times appeared to be some grand exercise in an elaborate piece of performance art. Damon Dash is 44-years-old and if you spend enough time around him, listen to his interviews, pay close attention to his candid social media presence, you can see that he is playing a character he is presenting to the world. Damon Dash is playing himself—Damon Dash starring in The Life of Damon Dash.

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It's a blustery afternoon in late March, just a few short days after the former Roc-A-Fella Records executive appeared on radio station Power 105’s morning show The Breakfast Club, and let loose on its hosts in a way that was loud, combative, opinionated, and funny. It was the Damon Dash of old, the one we have spent the better part of 20 years getting to know. The one who once lost his shit at a Def Jam meeting. The one who willingly shits on feared music execs like Kevin Liles and Lyor Cohen. The one with "Culture Vulture" issues with Complex Media and DJ Vlad and Funkmaster Flex and anyone else who just doesn’t see the world the way Dame Dash sees it. The one who just doesn’t give a fuck.

Today, I am not meeting that Damon Dash, until I am.

Questions about Kanye West and manhood and family find him expressively-candid, thoughtful, poignant, and emotive. He smokes a lot of weed—probably far too much weed—but when he is excited, his eyes, which belie some deeply guarded sadness, widen. He is jovial. He is humorous. He talks about the streets. He talks about the entertainment business. He talks about growing up. He talks about black people. He talks about white people. He talks about women. He talks about men. He talks about success. He talks about failure. He is charismatic. He has completely bat-shit views, views that people have but would never admit they have views. Some make sense. Some don’t. Whatever. He speaks with conviction. He speaks with confidence. Damon Dash is a born leader. I’m buying in. I’m on Team Dusko Poppington. And then I’m not.

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Continued below.

Dame Dash has strong views on family, entrepreneurship and old-school manliness—the kind of things talking heads on Fox News and right wing radio like to discuss—but when I ask him whether he realizes those things are part and parcel of the Republican and Conservative parties, his eyes narrow and his brow furrows. The veins on his neck bulge. He’s offended, angry, and doesn’t see the connection between him and Republicans. He’s a Democrat. “I don’t think I’m saying anything Obama doesn’t say.” He says he believes in paying taxes, even though he owes the I.R.S. back tax money, and says Republicans own oil companies, even though he has an oil company himself—Damon Dash Motor Oil. He says I’m racist because I favorably compare his enterprising stewardship of the black-owned record label Roc-A-Fella Records to Suge Knight and halcyon days of Death Row Records. “You compare me to a nigga that’s in jail,” he says. “That’s racist. Compare me to someone who is white.”

I get it. Sort of. If I were him, I’d be offended too. Or, maybe not. Damon Dash is confusing. I am trying to figure him out. Damon Dash the character is pissed, because Damon Dash the man is hurt. We laugh it off. The tension persists. It’s awkward. He makes thinly veiled threats; I don’t flinch. I’m not Kevin Liles. I’m not Lyor Cohen. I’m not DJ Vlad. I am a man. I will beat the shit out of Damon Dash. Or more likely, Damon Dash will beat the shit out of me. Fuck it. It happens. Damon Dash just wants his respect. Listen to him rant; listen to him rant!

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“I haven’t been in music in 15 years. I do fashion. Compare me to Andrew Rosen, who bought Theory and Rag & Bone. I don’t want to just be compared to Suge Knight. I don’t want to be in the same sentence. I don’t have a label. I have a division of music. I acquire companies. I’m not in the music business. I don’t do what they do. I buy companies. I sell companies. I create companies. I liquidate companies. I license out companies. I do a lot. I design, from the beginning, to the rooter to the tooter. I get a design, I go get the pattern, I go source the fabric, I go do the fittings. I was fucking educated in Savile Row. I learned how to make a suit in London.”

Did you hear that? Damon Dash learned how to make a suit in London.

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All quasi-confrontational bullshit aside, Dame Dash is a motherfucking legend. His early Roc-A-Fella Records moves alone place him somewhere next to Diddy, Russell Simmons, and Bryan “Birdman” Williams on hip-hop executive Mt. Rushmore. He introduced the world to Jay Z, and he built a label that included people like Beanie Sigel, Cam'ron, and Kanye West on its roster. For that, he always be a giant and always be revered.

But these days, he’s more immersed in projects like his art gallery, his fashion line, and his movie. But it’s what he says more than what he does that gets people going:

“If a man doesn’t want to be a boss, then he’s not a real man.”
“I’m not going to fight for something I don’t own.”
“How could a man say he has a boss and be proud?”
“Jobs are for lazy people who don’t want to invest in themselves.”
“Do you have to come to work today? Do you have a choice? Can another man say you’re fired? No one can tell me that.”

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These are some of the things he yelled at Breakfast Club host DJ Envy on the radio. In a day and age when most people aspire to one day tell their middling bosses to go fuck themselves—assuming, of course, they even have jobs in the first place—the Dame Dash school of life doesn’t sound that strange. In fact, it’s enviable. Americans are overworked, underpaid, and frustrated. We think this stuff; we just don’t say it. But there’s something about Dame’s empowerment program—something hard to place, hard to define. It’s a little unsettling.

“I’m not a Republican,” he says, whipping a lit blunt from his lips. “[But] the more entrepreneurs there are, the better it is for the economy. I’m just not with paying people who don’t want to work. It’s a complacency thing. Instead of giving people money, let’s give them an opportunity.”

Dame Dash isn’t like his cousin, the actress Stacey Dash, who supported Mitt Romney in the last election and recently told women to “stop making excuses” about the gender wage gap, but at times he really can sound like a conservative. It’s not intentional. He’s not even aware of it. He doesn’t have a political agenda. But if you listen to him talk long enough, you’ll see he’s on some Ayn Rand libertarian shit—living life on his own terms, unvarnished, unimpressed, unburdened by everyday bullshit—and he doesn’t have a ton of patience for anyone not on his page.

He talks about the streets a lot—the Dame Dash code of ethics comes from the corners he was raised on—but spits out boardroom lingo as if he was born inside one. And in the second half of his career, it can seem like he’s caught between those two worlds, everywhere and nowhere at once. He fancies himself a swashbuckling millionaire. A mogul. A tycoon. But these days he’s missing the outward-facing success, that one a-ha creation, to back his public bravado. Still, he’s cavalier. Just listen to him talk.

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On resilience: “Imagine you get punched in the face, you’re down on the floor, everyone thinks you’re out, but then you get up and you knock a nigga out. I love that fight.”

On gossip: “I think men are wasting their testosterone. Stop being in men’s business. Be like, ‘Yo, I’m a man with a vagina, so I’m not really a man.’

On violence: “If you don’t do what you’re supposed to do and treat men as men, then you get violated.”

On therapy: “Therapy is for women.”

In an era of extreme political correctness, when the finger-wagging internet mob can seemingly destroy anyone or anything it deems too “problematic,” Damon Dash, years removed from commanding the record industry empire that allowed him to be the biggest asshole imaginable, endures. His nonsensical platitudes resonate. He is a lion in winter, a real life character from a Martin Scorsese movie, the black Wolf of Wall Street. But life is not a movie and the ballad of Damon Dash isn’t opening in theaters nationwide this summer. He’s just a guy who has won a lot, lost a lot, and now finds himself caught somewhere in the middle.

“I’m human,” he says. “And if you turn your back, business is like boxing. You get in the ring, anything goes.”

Damon Dash has been beaten before. A $2.8 million unpaid tax bill has been hanging over his head for years and his most recent knockdown comes at the manicured hands of his ex-wife, designer Rachel Roy. In late April, she won custody of their two children and filed a restraining order. A few weeks ago, the police put out a pair of arrest warrants for him, claiming he owes hundreds of thousands in unpaid child support. As Dame Dash often does, he took to social media to lash out at the lawyers and at his ex-wife. In April, he slapped Roy with his own $2.5 million lawsuit. He got “fucked” on the fashion company they started together in 2005 and wants what he is due.

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“I got robbed in that moment for everything,” he says, suggesting that in 2009, back when his money problems really began, he’d invested far too much money into the company for the amount of debt it was carrying. “But it’s just business. It’s all part of the game. They won the battle, I’m winning the war.”

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Dame is a hard guy to get a read on. His moods change moment to moment. One minute he is charming (“The more the love, the better”), the next he’s threatening (“You disrespect a man and you’re unconscious of it, you don’t know what you’re gonna get— especially when you’re in his house”). He’s a little all over the map. Raised in East Harlem, Dash experienced a different era in New York, before gentrification, when neighborhoods were still neighborhoods, when where you lived really influenced who you would become. He ran the streets, busted guns, and saw death up close at an early age. Harlem was dog eat dog, and it shaped his worldview.

“I was raised around real men,” he says. “I look at the people that were violent and the reasons why— it was only to protect honor. Like, if someone disrespected you, where I’m from, if you don’t disrespect them back immediately, everyone disrespects you.”

Damon Dash would not be disrespected. He was intelligent, cagey, and combative—nobody could take advantage of him. He also attended predominantly white private schools, where he was exposed to a lifestyle he didn’t see living uptown. It changed him. Made him softer. But harder too, in a way. “When you’re going to a white school but you live around black kids you get real insecure,” Dame says. “You feel the need to prove yourself. I was a superhero to the white kids, cause I thought they were weaker than me, no disrespect. That’s reverse racism happening—I’m better in sports, I get all the girls, I’m fresher. But I always thought [about] whether or not I could be this dude in the street.”

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In the mid-90s, when he entered the record business as a manager of rap group Original Flavor, he would have his chance. Back then, the rap industry was transitioning out of its please listen to my demo stage and into the DIY independent label model. Tough guys flush with cash from the crack game were angling to get into the business. But you couldn’t just walk into a label asking for a record contract and you couldn’t just post your video to YouTube praying it went viral. You had to get hot in the streets first.

“I’m walking in a room with Jay-Z and you got guys telling me that they’re not going to sign him,” Dame remembers. “Steve Rifkind said he was going to sign him; that didn’t work out. Got him in front of Ruben Rodriguez from Pendulum Records; he was like, ‘rap!’ and we had to walk out like, like ‘get out of here.’ It was just disrespectful. He was the best rapper alive at that point in time, and people were shutting doors.”

It forced Dame to get resourceful. He got with Kareem “Biggs” Burke—a shadowy street guy who allegedly put up the dough to shoot Jay-Z’s “In My Lifetime” video (who is also currently serving a 5-year prison sentence on drug conspiracy charges)—and they started Roc-A-Fella Records.

“If I didn’t put those records out myself, you wouldn’t have ever known about Jay-Z,” says Dame. “There’s a lot of great ones out there no one knows about, cause no one was fighting for them. Not everyone had a Dame Dash.”

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There were many peaks and valleys to the story of Roc-A-Fella, but after ten years, the label was by most accounts a staggering success. Jay-Z was the biggest artist in music not named Eminem, and there were many successful artists and affiliated crews (Beanie Sigel and State Property; Cam’ron and the Diplomats, for example) signed to the company. Rocawear was reportedly bringing in $700 million a year and there were other businesses, too: vodka, magazines, MP3 players. And yet, something wasn’t right.

In 2004, for reason that still aren’t clear—was it over women, drug problems, mismanaged finances or an internal power struggle?—Jay-Z wanted out. Like out out, retirement level out. In the end, the trio wound up selling Roc-A-Fella to Island Def Jam for $10 million; Jay-Z became Shawn Carter the President at the parent company,while Dame got a short-lived vanity imprint called Dame Dash Music Group. A year later, in a $30 million deal, Jay bought his old friend out of Rocawear. Business as usual, but then Hov came out of retirement flipped Rocawear to Iconix Brand Group for $200 million. Did Dame Dash, the ultimate hustler—the name of his 2005 Apprentice-style reality show—get hustled?

“I know how much of a test it is to be honorable,” says Dame, without naming names. “It’s not for everybody.”

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A decade later, Dame and Jay are worlds apart. The general consensus is that Dame lost and Jay won, but that’s binary black and white thinking at its finest, and fails to paint the complete picture. There are bad feelings—a source close to him says Dash has problems trusting people because of the way things turned out—but the gap between the former BFFs is not as wide as people think. No, they aren’t texting about the NBA Finals, however the thought is not wholly inconceivable. Thank the children for that.

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“When I went to the Jay-Z concert [in 2013], do you think I went to go see the shit?” Dame asks, rolling his eyes. “I was with my daughter. She wanted to see it. I called Jay-Z after five years just because she wanted to go to a concert. We went to the back room. I played with [Blue Ivy]. It was great.”

Dame cares about nothing as much as his kids—“I hustle for my last name, not my first” is one of his favorite mantras (his son Boogie, for what it’s worth, is running a successful cookie company of his own now)—and if his daughter Ava wants to see a concert at the Barclays Center these days, she can text Jay directly for tickets. There’s no relationship per se, but both men are reasonably mature. They’re grownups. Fathers. No beef. Just businessmen no longer doing business. They’ll always have the memories—Reasonable Doubt, the logo, “Big Pimpin,” Kanye.

Ah, Kanye. There, the relationship is different. Dame inked ‘Ye to his first real record deal, and though they fell out of touch post-Roc-A-Fella break-up, the past few months have seen Kanye and Dame sidling up to one another again. It started with a phone call.

“I was listening to old Kanye music,” Dame says. And then days later, as if on cue, the phone rang. ‘Ye wanted him say a few words about him at the BET Honors.

“He said some interesting things up top, but I had to address what was on my mind,” Dame says. “There were some issues—he hasn’t supported Biggs; he hadn’t invited me to the wedding. He addressed it, honestly, and we moved on.”

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In the mid-aughts, when Dame left music—or music left Dame—he had a butler, personal photographer, Maybach, and residences in Beverly Hills and Tribeca. The emperor wore new clothes, literally, every single day. But after years of loudly battling with vulturous record executives to get his way, he had a shifty reputation. Depending on whom you ask, he was flat out blackballed. Then, the recession hit. Businesses went bust, apartments got foreclosed on, lawsuits piled up, and he got divorced.

Looking to rebound, Dame went underground. He opened a sprawling multimedia arts space/club/gallery in downtown Manhattan, DD172, and launched a new record label BluRoc, where he worked with artists like Curren$y, Jay Electronica, Mos Def, Jim Jones, and the Black Keys, among others. There wasn’t a specific breakout hit, and he claims the Black Keys, in particular, did him dirty (“The minute I put them on, they went and jumped [the other] way. What is it—because we’re black, they don’t want to be on the road with us? The Black Keys are racist?”), but in its time, DD172 was quietly influential. Then in 2011, the city of New York busted the gallery for selling alcohol illegally, and the Dame Dash comeback party ended.

“It was perfect,” Dame says. “I did everything. Nothing went wrong at all. There was no expectation. The history that got made there is priceless.”

But in entertainment you’re only as hot as whom you’re standing next to, and for the past few years Dame has often stood alone. Sure, he still works with guys like Cam’ron and battle rapper Murder Mook, and behind the scenes he’ll still sought for his council, but in the context of the larger landscape, he’s a man apart, playing in his own sandbox, albeit one that he constructed with his own wood, in his own backyard. The BET Honors, however, gave him a rare chance to be on someone else’s turf. And yet it was still… awkward.

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“I do white people shit better than white people; you can’t out white people me,” Dame explains. “[But] it’s the black people that are high yellow— because they cut with other cultures— who were gangsters years before; as soon as they got they money, they got snobby to hide all this shit. So at [BET Honors it] was a whole circle of [people from] black colleges like Howard and Morehouse. It was like the high end of all the high yellow out there.”

Perhaps perturbed by this, Dame nervously took the stage at the show with his daughter in tow, stumbled over a few words, and then delivered an awkward and at times terribly uncomfortable speech. A lot of it, not surprisingly, was about himself. It was both charismatic and cringe-worthy at the same time. And yet at its heart the message was there—Kanye was a courageous artist, and Dame respected him deeply.

“[Kanye] was brave enough to walk into a room and get teased,” Dash said. “That’s what I liked about him.” He talked about Kanye’s mother. He talked about Kanye’s strength. He talked about investing in Kanye when nobody else would, said he was mad they weren’t making money together anymore, and practically pleaded with him to throw him a life vest. “Invest back,” he said. It was a father talking to his son, begging him to let him back into his life. It worked.

“We’re going to work on films,” Kanye told Power 105 in February. “I really like the films that [Dame is] doing.”

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Almost immediately, Kanye was added as an Executive Producer Dame on Dame’s first directorial effort as a filmmaker, Loisaidas—as well as Too Honorable—and in a video posted to Dame’s Instagram account, the pair touted plans, albeit premature, to purchase the bankrupt online retailer Karmaloop. Dame Dash and Kanye West, the most important artist in all of music, are back in business.

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Damon Dash is wickedly smart. He talks a lot and sometimes doesn’t make much sense. Or, maybe he makes a lot of sense and people just don’t get it; because sometimes you’re so far ahead of the conversation that it looks like you’re the crazy one. Either way, his is not a quiet mind. He’s always thinking, strategizing, coming up with angles, seeing things others aren’t.

“I’m very direct, and I just tell the truth,” he says. “To some people that’s bad; some people it’s good. In certain worlds, where people are evasive, and they want to project they’re perfect, then I’m crazy. I don’t believe I’m perfect. I embrace my imperfections.”

Those imperfections seem to be what are driving him now, leading from one project to the next, the master plan being that there is no master plan. In March, Loisaidas, which he self-funded and pushed forward creatively, was his main concern. He released it direct to the internet—“Netflix won’t return my calls, but fuck it, I don’t have to be humble,” he says—and while critical reaction to the film has been muted, the right people, namely the streets and the internet, have embraced it. The accolades may never come, but it’s a decent film. In April, it was all about the Poppington Academy, a Learning Annex-style seminar for aspiring moguls and creatives. Then he began rolling out chapters of his online audio/visual book, Culture Vulture, where he spews the gospel according to Damon Dash over densely layered instrumentals. Now, it’s all about his next film, Too Honorable, a gritty crime drama which sees Kanye West again in an executive producer role, due out May 25.

Perhaps most importantly, the dust may be settling on a variety of the behind-the-scenes issues that have been hanging over his head. Arrest warrants aside—to the uninitiated, warrants sound scarier than they actually are— a major lawsuit against director Lee Daniels over cash that Dash loaned him early in his career was settled in early April, and according to the Hollywood Reporter, it will yield an opportunity for him to work with the Empire creator again soon. A fence mended with one of the most powerful people in Hollywood, and Kanye in his pocket—even Stevie Wonder can see where things are headed. This is chess, not checkers, after all.

Or, maybe Dame Dash the character, the one whose whose fuse can be lit by the odd off-putting question of a journalist or a radio jock, will keep Dame Dash the man stuck in the shadows, where he’s been for the past umpteen years. Maybe under the towering spectre of brand Jay-Z, the gossip columns, the I.R.S., and the lawsuits, he’ll continue toiling away in the dark. Making quiet money. Making money quietly. Talking loudly. Saying wild shit. Going viral. People listening. People not listening. The neverending cycle repeating itself. Always the character, the Dame Dash people want, but maybe not the one Dame Dash needs.

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I am still sitting in Dame Dash’s loft space on the Lower East Side of Manhattan. It is still named Poppington, and still bills itself as an art gallery of sorts. There are a few paintings hanging on the walls, but the most profound piece of work has been sitting across from me for the past 90 minutes.

Mostly, Dame Dash is a nice, friendly guy. He’s a grownup dude with grownup responsibilities and childlike compulsiveness to keep busy. But at the moment, he is just a man who is slightly more annoyed about a question I’ve asked him than he will care to admit. He is insulted. “I don’t think it was personal,” he says. “I don’t think it was intentional.” But there’s still aggression in his voice, a shift in his body language. He gets up to walk it off and I learn that like the many faces of Damon Dash, this one too, is just temporary. Dame Dash, like teenage child sitting home alone in his bedroom, just wants to be less misunderstood.

“No one understands the game I’m playing,” he says, clarifying his dismay. “So that’s why I be talking to people and they be like… You don’t know what I’m doing. There’s a jaded perception from the press. I’m trying to be LVMH (Louis Vuitton Moët Hennessy), but also have a communications component. I’m savvy with selling things direct to consumer, but I’m also savvy at being an opinion leader.”

Either way, he is defiant, contrarian, in his own world and completely OK with that. He pauses, locks gazes and deadpans.

“I’m just good at a lot of shit.”

Paul Cantor is a writer based in New York City. Follow him on Twitter.