No one even pretends to do a double take over Jay-Z's longevity anymore. Remember, during his "un-retirement" period, circa Kingdom Come, when there was question about whether he could still bring it? Those questions don’t get asked so much these days. Jay is pushing 42, and this summer he’s got a brand-new throne for us to admire. His collaborator, Kanye West, who just turned 34, makes it hard not to conceive how he could still be relevant, if not dominant, half a decade from now.

For a form that used to chew up its legendary innovators with an astonishing quickness (Rakim, what happened?), this is a noteworthy, and relatively recent, development. “Well, you’ve cherry-picked the genre’s top star as an example,” one could object. But it isn’t just Jay who has blasted past the most imposing barrier to middle-age success. More and more, we’re seeing veteran artists extend their commercial viability in what has long been known as a young man’s game. The conventionally accepted life span of a rapper is changing. As 40-year-old rappers become the norm, the question becomes, when will they stop? And why would they? Hell, the way things are looking, Dre might be 50 years old by the time Detox finally drops. Call it Energizer Bunny hip-hop. They keep going and going.

What has brought about the change? And what are the secrets to aging gracefully in rap? As different as every long-term career in rap tends to be, there are some broad similarities. The fan base that supports an MC’s first act usually is not sufficient enough—or doesn’t stay cohesive enough—to sustain a decades-long career. For rappers with that ambition, this reality requires constantly finding new allies, as well as going out and discovering pockets of affection the rapper didn’t even know existed in the first place.
It was only through his recent touring with Kansas’s Tech N9ne, who turns 40 in November, that Bay Area mainstay E-40 found out about a new strain of hardcore fan. “You’ve heard of the Juggalos?” says 40, 43 years old himself, of the crazed cultish devotees of Detroit’s Insane Clown Posse. “Not everybody know that, but Tech got an established fan base. I did a 43-date tour with Strange Music. And it was quite interesting, because I went to places that I didn’t think was fuckin’ with me yet. Everywhere—all down the East Coast, Midwest, South—we hit every angle… There’s a lot of Juggalos out there. They be fired up. What’s that, ‘mosh pit’? They be doing that in the crowd. And I just tripped on that. The response: They knew my hood shit; they knew everything. You’d be surprised.”

After a full decade in decline, the 43-year-old Raekwon has been experiencing a powerful resurgence since his widely acclaimed 2009 comeback, Only Built 4 Cuban Linx…Pt. II. It’s a resurgence that has come with a certain shift in demographics, too, as Rae and his Wu-Tang compatriots have become favorites of the indie-rock fans who center around and have taken—as has been a trend in various musical genres of late—to performing some of their classic 1990s albums in their entirety. But Rae got a whole new perspective on the reach of his legacy this past spring, when Illinois Republican State Senator Christine Radogno rose during a floor debate…to cite a banger from one of those albums.

“Some of you may know that, last night, Raekwon from the Wu-Tang Clan was in town,” Radogno said, throwing a long, Midwestern twang into the last syllable of the Chef’s moniker. “And I got some financial advice from him, which I would like to share with all of you, because it does seem quite relevant.”

Radogno proceeded to bite a portion of the script from the classic Chappelle’s Show sketch “Wu-Tang Financials,” in which Raekwon made a guest appearance touting a financial-advisory business based on the lessons put forward in the group’s 1993 hit “C.R.E.A.M.”

“The most precious thing in the world is the financial security and well-being of your family,” Radogno said, quoting Rae. “You want to send your little ones to the best school, and in the end, you want to know you’ve left them with peace of mind. Nowadays we all know that cash rules everything around us: C.R.E.A.M. Get the money. Dollar, dollar bill, y’all. Thank you.”

“I heard about it,” Raekwon says, still sounding amazed. “This is something that wasn’t premeditated for me. It was just love. At first my peoples told me about it. I was like, ‘What they tryin’ to do, label me on some Fidel Castro shit or something? What’s going on?’ But then, as I took a look at it, it wasn’t nothing disrespectful, you know what I mean? And honestly, when I tell you I was shocked, I was only shocked at the people she was saying it to. All you see in there was suits and books, you know?

“Maybe she came to the show that night and was coolin’ with her girlfriend or whoever, and they was like, ‘Wow, this is an intelligent kid.’… I think I’m a smart dude. I think I have enough common sense to show another side of me, and maybe she seen that.”