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Lil Dicky Called His Shot 5 Years Ago Saying He’d Parlay His Rap Career Into TV

Back in 2015 at Irving Plaza, before a live show on the Professional Rapper Tour, Lil Dicky was kind enough to give me some time for an interview on Mailtime. I thought it was a wild move. I didn’t think any artist would wanna be bothered by an interview just a couple hours before he hits the stage. I remember when I was covering the Mets back in college at WFUV, I broke the cardinal rule of approaching Tom Glavine for a sound byte on a day he was pitching. It was fucking SPRING TRAINING, and Glav turned me down. The reporters all looked at me like I had spit in his face, attempting to ask a question to a man who had to pitch a fake game in 3 hours. But I learned that day that when people are expected to perform, you don’t bother them with your nonsense questions. 

Anyway, Lil Dicky was no Tom Glavine. He invited me backstage to his green room at Irving Plaza, a place I had been many times before for the Barstool Blackout tour. And we sat down and LD delivered this unbelievable interview. A half hour convo about who he is and what he was trying to do. A deep dive into what he was all about, and what he was trying to achieve, all along the journey to find his soulmate. That was Lil Dicky’s main goal - to find his soulmate. A deeply romantic and introspective dude who happens to have a leftward sloping penis and a knack for spitting multisyllabic rhymes and making people laugh.

And so I asked him I if he considered himself a rapper or a comedian. And that’s when he delivered this sound byte that Chuck dug up today while listening to an old school episode of the first iteration of Mailtime. He told me he was a comedian using rap as a vehicle to become a writer and have his own TV show. Fast forward 5 years, and whadda ya know, “Dave” is one of the funniest and most successful shows on television. Do you know how fucking COCKY it is to call your shot like that? 5 years in advance, tell everyone that you’re using your skills and background to game the system, to gain exposure, to eventually dominate a field to which you currently, ADMITTEDLY, have zero ties?? At the time of that interview he had no reason to believe he was going to have a successful TV show other than his rap skills and his belief in his own comedic writing. And he laid out exactly how he was gonna make that jump from humorous rap to television comedy, and he did it in a crazy short period of time. 

And you can say to me that anybody who’s ever made it big has had a moment like this where they called their shot. But the difference here is LD was well on his way to being a successful music act. By some standards he absolutely already was. And by other, higher standards, I’d say that the Long Winded Answer was going to be a massive rap/pop success. It would have been easy to just say, fuck it, let me just keep crushing this rap thing. But the goal was comedic writing. It was that back in 2015, and probably many years before that, and it was the goal in 2019 as well. Dude stuck to the plan, and now can consider himself a triple (quadruple? Quintuple?) threat. Unreal. 

One of the best examples of confidence in the modern world of content and technology you will ever see. If the Independent Variable was in any other genre, at any other time period, with even 1% less confidence and faith in himself, maybe he’s still just making funny music videos. Instead he’s got a TV with 4.8 MILLION viewers across all platforms, which is 2112% higher than FXX’s average TV show. Surpassed Atlanta as FX’s most watch comedy ever. BOSS shit. Congrats to The Human Bitcoin, Cheeto Santino, and everyone who put their balls on the table and made it happen.