A radio interviewer on Hot 97 asked Jay what he thought of Dash and his money troubles. He said, "I can only have love for Damon," because of what they created as young men. "I have ultimate confidence in him that he'll find his way, because he's an amazing and really smart guy." Representatives for Jay-Z declined to comment for this story.

At the Jones show, Dash does not seem like a man with 99 problems, or any. "The news has been talking about the same tax shit for five fucking years," he says, weaving toward the stage, where Jones is finally rehearsing. "Oh, he's fucked-up. I ain't going bankrupt. Everybody's waiting for it. Every single year, everyone's focus is my pockets. And they ain't even worried about what I'm doing—only what I'm holding?"

A few minutes later, as I watch Dash in the smoky basement that serves as the Mercury Lounge's green room, it's hard not to think about his and Jay-Z's divergent paths. Jay is on the cover of Vanity Fair, in a concert documentary shot by Ron Howard, trading texts with Obama, and negotiating a $240 million contract with the Seattle Mariners for Robinson Cano (oh, Jay-Z is a sports agent now, too), while Dash leads a crew of strivers who skitter about as Jim Jones learns his lyrics.

But there's no envy. No humility. Dash is as brash and as boastful as the guy speeding around on a (borrowed) boat full of babes. "When I see Jay on a magazine cover? That's me," he says. "I'm proud. I don't see why that means me against him. It makes me look big. I don't understand. How does that not make me look big?"

He turns his attention to Jones, who sits with his head hanging low. Dash tells him to think like a rock star. "Like Jim Morrison, man," he says, ducking under a graphic tee hanging from a heating pipe. "Shit is hot up in here!" Dash yells. "This is the real shit!" He stands over Jones like a boxing trainer exhorting his fighter between rounds. "Somebody get this nigga high!" Dash says. He is met by a dozen glazed stares. "Nobody got weed? Y'all smoked it all? Before the show?!"