Tales of a Jewish Rapper: An Interview With George Watsky

Best known for his music, rapper George Watsky got his start in spoken-word poetry. He became a rhythmic and fast rhyming voice for millennials after his video “Watsky Raps Fast” went viral in 2011, kicking off his music career. At the age of 29, he has already produced a number of albums the latest of which, All You Can Do, peaked at #6 on the iTunes charts. Lin- Manuel Miranda, creator of the hit Broadway musical Hamilton, called Watsky one of his “favorite rappers of all time,” and, yesterday, Watksy launched his first collection of Essays called, How to Ruin Everything.

While this honest and humorous account details the things one might expect from a rapper on the road including puking in hotel room toilets, auditioning for porn-star like roles in LA, rolling around with with redheads in the fields of the Midwest, doing cocaine and parties in Los Vegas, the collection also holds insightful nuggets of wisdom and takes a witty approach to dealing with moments of failure, humiliation and adversity.

In perhaps the most poignant essay, Watsky tells the story of his father’s best friend, a therapist who struggled with depression, revealing the inspiration for one of his songs, the Wounded Healer. He begins by describing the complex relationship his father had with his grandmother who, like many Jews of her generation in Manhattan, was raised in poverty during the depression. “If you asked her how she was,” George told me, “she would say, ‘I can’t complain’ and then she would launch into a 20-minute complaining session.” In the essay, George describes his father’s die hard but cautious support for the San Francisco Giants writing, “like many Jews, they knew excitement is dangerous; the more you invest, the more you’re devastated by the let down.”

Watksy independently funded the creation of his music videos, which later went viral, by performing at hundreds of college campuses across America between the years 2008 and 2012. The book describes his time on the road, painting a picture of despair that cast a shadow over rural American towns.

When I asked him about touring these empty towns of the Midwest, George explained that there is sadness to it but also a kind of gratification. “I’m performing in a part of America that had this huge boom after WW2,” he said, “It was the engine of the American economy and it’s not anymore. There’s a sad feeling that pervades these closed main streets all over. I was representing a previous version of America both in terms of being a small town in the Midwest as an economic driver and as a white person.” He explained that America will become so much richer in its diversity in the future and that he isn’t sad to see an old institution of power disintegrate. “The straight white male as a power structure is becoming a dinosaur and I don’t think that’s a bad thing.”

Watsky sees a bright future for poetry saying, “I don’t think poetry will ever become obsolete. There will always be new generations that discover the power of a poem. You’re seeing a lot of new poets rise up on the internet right now.”

So why write an entire book about life’s failures? “There’s nobody that can say they didn’t fail a lot of times before they succeeded,” Watsky said,  “I hear ‘no’ more times than I hear ‘yes.’ The only way to lose is to let all those minor stumbles defeat you.”

When I asked Watksy if he would ever perform in Israel he said, “I’d love to come to Israel That’d be awesome!”

How To Ruin Everything  launched yesterday and is available at all major bookstores and online.