Rabbi Darkside on Bringing Prospect Avenue Around the World


Few underground hip-hop artists in New York have had the staying power of Rabbi Darkside. From an era where everyone had a vinyl single, through rap battling at the start of the mid-2000s rising next wave of battle leagues, to being a coach on “MTV’s Made” and one of the centerpieces of the Hip-Hop Subway Series, if there’s been a major hip-hop event in the city, chances are he’s been a visible presence. In further evidence of how he’s been able to change with the times, he’s recently become one of the few hip-hop artists to successfully use Kickstarter to fund his new album Prospect Avenue, which he’ll be unveiling at the release show on Friday at Brooklyn’s Littlefield. We spoke to Rabbi Darkside on how he’s always managed to remain a constant presence in such an ever-changing turbulent scene.

See also: Peter Rosenberg’s What’s Poppin’ Vol. 1 Takes The New York Hip-Hop Scene’s Pulse

How did your new album Prospect Avenue come together?
It came together over a couple years. A cool year of writing, a year in the studio and the concept came about as I developed the material for it. There’s certain people I knew I wanted to have on it, so after a lot of convincing myself you’re not going to know unless you ask, I had a pretty good success rate getting people I admire to get on the record like Da Beatminerz, Rob Swift of the X-Ecutioners and Homeboy Sandman.

In a world where there seems to be two Kickstarters for every rap artist, why do you think yours worked?
That’s a good question. When I finished the album, I knew I wanted to spend as much or more money releasing it as I spent making it. I broke the bank on recording, mixing and mastering it and I wanted to make it feel like as big of a budget record as I could even though it was an indie record that I was funding myself. So, I came up with a business plan to shop it to prospective indie labels. That didn’t pan out, so I crossed my fingers to find some angel investor independent financier. I don’t know how realistic that was, but that didn’t pan out. So plan C was to crowdsource it. I basically applied my business model to Kickstarter and spent three months developing the campaign, rewriting the text, devising a trailer video, and in this digital era I tried to pitch it as high art for people to invest in what I represented as an artist. I treated the campaign itself like a piece of art, and I think that really came across. I think the inspiration people felt from seeing the campaign came back tenfold, and that inspired me to hyper-personalize the campaign and really invite people into my world, which is a hard thing to do. I didn’t want to be annoying, which I think is one of the biggest obstacles you run into when running a crowdsourcing campaign. My videos weren’t me looking into a camera making a direct “Ask” which most people do. Once the ball got rolling, I made these roll call freestyle rap videos to everyone who contributed that week. That really helped fuel the momentum and inspired some people to even increase their campaign donation. My magic number was 200 unique backers, and I exceeded that by quite a few people and exceeded my goal by 125%.

Do you recall your first entry into the New York underground hip-hop scene?
I moved here in 1999 from Buffalo, New York for the summer between my junior and senior years in college. That summer was completely insane, filled with Black Lily Jam Sessions at the Wetlands and Summerstage shows. As a visitor during that point, my introduction was Central Park cyphers and cyphers down in the Village. I remember being at S.O.B.’s with Common just chilling in the spot. Meeting rappers on the corner or in Washington Square Park were some of my earliest memories of New York hip-hop.

What’s the biggest difference between the underground scene then and now?
I think, 13-years-ago there was a real sonic and content difference beween what was underground and what was not. There was a real “anti-jiggy” mentality that defined the underground. “Backpack vs Glam” was a real thing. You could see someone and affirm from their attire if they were into underground hip-hop. It’s not so clear-cut anymore. There’s also not as much freestyling between rappers at shows as there used to be. A lot of that energy lives online now, you used to have to get out to interact with people. Plus, up-until 2004, there was no way for a DJ to play your instrumentals unless you had vinyl pressed, so that changed the live show element for the better for me.

See also: Ten Great Neighborhood-Specific Brooklyn Rap Anthems

How were you able to parlay your underground hip-hop success into worldwide touring?
My first international adventure was September, 2007. That was to Prague to celebrate the release of the first Czech human beatbox album. It was created by Jaro Cossiga who I met in 2006 through [beatboxer] Kid Lucky and that lead to us collaborating on a track. Thanks to the power of the internet, we were able to exchange files and make this record together. I was the only international guest on the record, and since they had some pretty serious sponsorship to get this record put out, they had money to fly me to Prague. Basically, the connections I made meeting international hip-hoppers in New York City, allowed me to set-up an international tour that summer.

What’s the Hip-Hop Re:Education Project that’s opening up Friday’s show?
It’s a multi-faceted youth organization that I co-founded which relies on the hip-hop elements as teaching elements. It is a five-borough-wide organization that uses hip-hop culture to inspire and transform communities and engage and improve youth motivation and achievement. We do three things primarily: an all-city “out-of-school” workshop series for young people that culminates with a inter-borough youth rap record, we do curriculum design and direct instruction, and we facilitate international youth hip-hop exchanges where young people from Berlin for cultural immersion, and we send a group of young people from New York to Berlin and we’re planning our first trip to Barcelona.

13 years after your first time rapping on a New York stage, how is Friday’s show in particular going to be different?
This show [will be] a real celebration of independent art culture in New York City. Everyone I’m collaborating with on the release of the record is an independent entrepreneur. From the Brooklyn-Queen t-shirts printing the tees to Wandering Star brewery brewing a special Prospect Avenue Darkside Ale to the CD and Vinyl pressing plants, this is really intentional. It gets back to why the Kickstarter was successful. I’m doing all of this independently, and I wanted to approach it like the Green Bay Packers and give the fans a chance to buy into the team. I think that appeals to people.

The Top 20 NYC Rap Albums of All Time: The Complete List
Hip-Hop’s 25 Best Weed Songs
Sorry, But Kanye Is the GOAT