Wiz Khalifa and the Ones Who Never Made It

Wiz Khalifa’s got a new album out today — Khalifa — which, depending on your listening preferences, you may want to check out. Or, you may not. It’s up to you. I have no idea what the hell anyone listens to anymore. It seems like Snapchats have more shelf-life than songs these days, but who am I to say.

Anyway, I probably wouldn’t be writing this if I didn’t realize that on the occasion of this being Wiz’s 6th album — not including his countless mixtapes, which are arguably albums, too — it’s also coming up on 10 years since I set out to write a short little profile on Wiz for XXL magazine. It was a thing they used to do on new artists, Show & Prove it was called. It took twenty hours of work for an article that was 300 words, and for whatever reason, Wiz was due to be featured.

He was set to perform at a new artist showcase at S.O.B.’s nightclub — I think, if I’m not mistaken, it was part of Allhiphop.com week, or something like that — and in order to write the article, I needed to interview him. So I interviewed him sitting in a corner booth towards the back of the club, about an hour before the show. He was 18-years-old, but looked all of 12.

One thing about rap shows, they’re never organized very well. Wiz, I believe, headlined that show, but that meant he went on last, hours after the show began. By the time he hit the stage, there was — no exaggeration — like, 10 people there. They were probably Pittsburgh transplants. Or friends of his managers. I have no idea why anyone would wait around that long to see a new artist unless they had some sort of personal or professional relationship with the guy.

Anyway, I wrote the article and then the strangest thing happened — the editor killed it. I guess she felt it wasn’t the right time, that maybe his buzz wasn’t big enough to warrant the coverage, or that she wanted to cover him later. I have no idea. Magazines can be very political and there are a lot of question marks surrounding why certain things happen and why they don’t.

It turned out to be the right move, because a year later, Wiz signed to Warner Brothers. If there was a time to cover him, it was then, not the year before, when I was doing my little piece. And yet, the Warner thing didn’t really work out for him. He had that one song, “Say Yeah,” which people liked, but I don’t think the label really knew what to do with him. He was from Pittsburgh and it’s like, how does a major label break an artist from Pittsburgh? What would they know about that?

All through that time though, I would occasionally check out his shows, since he performed rather frequently. And just like that night at S.O.B.’s, in front of 10 people, he always gave a very energetic performance. Lean and wiry, he kind of bounced around the stage almost like Gumby. His music, too, was perfect for live performances, because he was never a rapper who got lost in his notebook. His lyrics were easy to recite.

At one point, I remember him touring with Girl Talk — remember Girl Talk? — another Pittsburgh native, and he was actually opening the show. He did a gig on the Williamsburg waterfront in Brooklyn, it felt like every white person in the borough was there, even though they didn’t really know who he was. Weird scene, for sure.

But all the while, he just kept working, kept releasing music, and over time — even though most critics never really warmed to him — he earned his fan base, little by little. And in 2010, when “Black and Yellow” pushed him into the mainstream (fun fact: I actually heard the song in the studio the day it was recorded), it wasn’t like he’d just popped up out of nowhere. His thing was already in motion, he just needed something to make everyone finally pay attention.

Wiz Khalifa has released many albums since then, and heck, I’ve been to a handful of his shows. I’ve covered him from time to time, written this thing or that thing. And through it all, I’ve just kind of enjoyed — from a distance, of course — watching how things have panned out for him.

I gather that during the course of any artist’s career, like life itself, there are peaks and valleys. Some albums are gonna hit, some are gonna miss, some are going to be just okay. Things are up, down, then they’re up again. The cycle continues.

It is though, remarkable, that ten years can by pass by, almost like a blink of the eye, and someone who sat across from you at a table — without having much to say, ultimately — can now be knee-deep in a life, in a career, that seems so… full. This, of course, on the heels of it potentially not happening at all.

I sometimes go back and look at that article I wrote, mostly cringe at how bad it is, and then think about all the other artists I’ve written about, the ones who had all the momentum, all the buzz, all the ducks in a row, the blueprint for success mapped out. The ones whose articles made it into the magazine.

And then I think about how few of them actually made it, how so many of them just faded into the background, never to be heard from again. Maybe they’ve got desk jobs now, or work security at Home Depot. The second life for failed rappers is usually not a noteworthy one.

But among others who I wrote about, Wiz Khalifa is one who made it. I mean, really made it. Which goes to show, you just never know. You never fucking know.

Written by

Wrote for the New York Times, New York Magazine, Esquire, Rolling Stone, Vice, Fader, Vibe, XXL, MTV News, many other places.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store