I'm a 40-Year-Old White Guy Trying to Have a Rap Career. Is the World Ready For A$AP Fogey?

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Dear Fan,
I am a 40-something-year-old white guy. I have long hair, like rock music, etc. Basically I am into all things white dudes are into. However over the last few years I have really immersed myself into the rap world.

I saw a Jay-Z commercial last night and found it very inspiring. Well, inspiring enough to get me thinking that if I could make just ONE top 20 rap hit I could be set for life. Then I could start having babies and not worry about their future.

Could you tell me how to break into the rap game without a lot of effort?

I feel like my flow, were I to ever give this a go, would probably be a cross between Debbie Harry on "Rapture" and Pete Nice.

This is 40

Dear 40,
Last year I breifly held a position recapping season three of The Voice for Rolling Stone, and aside from the lucid and horrifying sorts of Slouching Towards Bethelehem moments of peering into the blank void of America's soul that only talent competitions can provide, I witnessed a moment that spoke about the nature of fame and the elusive satisfaction of having just one hit.

Ok, so Cupid -- of "Cupid Shuffle" fame -- came on, in hopes of showing all of America, that he is more than just "Cupid Shuffle." He wanted to show that he is someone who could have more hits, more than this one song that was totally huge but did not make a career. Anyhow, so he comes out for his blind audition with the audience and judges and inexplicably performs "Cupid Shuffle," for confusing reasons -- but in part because it's a song people know and love. And none of the judges picked him for their team, but when they turned around Cee-Lo immediately yelled "Cupid!" and was baffled, asking him "What are you doing on this show?"

So, that is my lesson: one song, even if it is huge, guarantees you nothing. Other than a life of time of living in the shadow of the memory. Or Cee-Lo recognizing you. So let's put that thought to bed, shall we? Then, the question becomes "Is 40 too late to launch a rap career?" I don't think it is, honestly, but I reached out to someone who has some experience with this subject, Slug from Atmosphere.

"Now that we have 40-somethings who grew up on the 'hip to the hop,' there's definitely a market for his old man raps," he says. "He should obviously stay away from trying to fit in with the younger dudes. We don't need an A$AP Fogey." He also suggested some ways to appeal to your self-same demographic: "He should make raps about the struggles of mid-life: hamstring stretching, low-carb meals, and the frustrations of being smart-phone-stupid."

The other thing to consider here is: If you are to really become a full-tilt success you have to have a broad appeal. Kanye is only a little younger than you, Hova's about your same age and they are equally beloved by both tiny school children and out-of-touch Wilco Dads™ (dads who only keep up with new Wilco releases, not the dads of/in Wilco). Do you have something to give you transgeneration appeal? Do you have a "Thrift Shop" in you?

I posed your question to Larry Jackson, the Executive Vice President of Universal Music Group, who signed two of pop's biggest internet-borne sensations, Chief Keef and Lana Del Rey. He says that, with the internet, your chances are as good as anyone's. "With ingenuity and knowledge of where to plant the seed on the web, anything is possible. I say that not to give false hope or patronize. Someone sees a 40 year-old white guy rapping and the song is funny or has a touching, poignant message, if it moves you emotionally, makes you feel something with its humor or despair -- the world is your oyster." From there, once you have connected with an audience, he says, you just need the knowledge of how to fan the flames.

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