(AllHipHop Features) The San Francisco raised performer decided to venture into another realm of entertainment by penning a series of humorous essays.
Those 13 writings have been curated into the new book How To Ruin Everything. The 230-page collection chronicles various moments from Watsky’s life such as battle rapping in middle school, traveling overseas, and suffering epileptic seizures.
The All You Can Do album creator’s first literary work has garnered praise from several high-profile individuals including other writers, Hip Hop mogul Russell Simmons, The Daily Show correspondent Hasan Minhaj, and Hamilton creator Lin-Manuel Miranda.
“Funny, subversive, and able to excavate such brutally honest sentences that you find yourself nodding your head in wonder and recognition,” writes Miranda about How To Ruin Everything.
AllHipHop.com caught up with Watsky to discuss his latest effort. The Emerson College graduate also touches on what’s next on the music front.
Why did you decide to write this book now?
I’ve always bounced back-and-forth between different forms since I started writing as a teenager. I started doing spoken word poetry and music at the same time. I studied playwriting and screenwriting in school, so working in different forms is always something I really wanted to do.
I had a lot of stories I wanted to tell. I wanted to try something new. I’ve been on the road for about four years, and I found a formula that was working for me. So I wanted to try a project that made me feel a little less comfortable.
How did you decide which stories you wanted to include in the book?
When kids come up to me after shows and they’re writers, I always tell people the main thing they should focus on is writing about the things that fascinate them. That’s pretty much what this book is for me. It doesn’t really follow a theme. These are just things that fascinate me.
You’re meant to jump back-and-forth between essays. Some of them are more personal, some are more political, some are funny, some are serious. It’s the book form of what it would be like to have a conversation with me.
You got a lot of praise from different people. How does it feel to have established writers praising your work?
It’s cool. I went to all these people and asked them to say nice things about my book. So on the one hand, it’s super dope to have people that I look up to coming to bat for my book. But, I want to acknowledge they’re also friends of mine and have an interest in seeing me succeed.
It was a humbling experience to go to folks I really respect and ask them for those favors. The fact they were down to really put their reputation on the line for my book meant a lot to me.
The Cover To Watsky’s Essay Collection
As you were going back and retelling these different things happening in your life, what were some of the emotions you went through?
It’s definitely a therapy project about trying to admit things to yourself that you might have pushed down. Also, another big thing I was thinking about is the other people that were in the stories and how they came across. It’s a tough line to walk between wanting to tell the truth but not wanting to burn bridges with people in your life that you care about.
They didn’t sign up to have their flaws exposed publicly. I don’t mind making myself the butt of the joke. That’s the career I signed up for. Being honest about my flaws and shortcomings is what I do for a living. But to drag my family into it, that’s another thing.
What were their reactions when they read the book or when you told them about it?
I let everyone who was included in one of the essays read a draft of it before I published it, before I even finished. I wanted everyone to know I wasn’t trying to smear them. I was trying to be transparent and give them the opportunity to tell me if it was something that was really going to hurt them.
There were a few little details that folks asked me to remove, but for the most part, it wasn’t anything major. I think that everyone I showed it to really appreciated that I went to them upfront about it.
There were some times where people felt unflattered by things that I didn’t feel was unflattering for them, but I tried to put myself in their shoes. I got a lot of good responses from everybody.
Now that you’ve done this endeavor, are you interested in doing more writing like non-fiction or screenwriting?
Definitely. I did a short film adaptation of one of these stories, and it went over really well. Honestly, it went over better than my music. I have fans that really love my music, but it’s polarizing for people. But the short film adaptation for one of these stories had the most consistent positive feedback for anything I’ve put out.
That made me feel like there might be a future for me. I studied screenwriting in school, and the response really made me feel like it’s something I should keep pursuing. I’m not going to stop the music, but screenwriting is something I’m interested in.
Speaking of music, what’s the status of your next project?
I’ve been working on new music. I’m moved to New York in September, and I’ve definitely been busy while I’ve been here.
So no timeline yet. You’re just recording?
Yeah, no timeline yet. But it’s not going to be a long time.
What do you hope readers take away from reading your book?
The thing I’m interested in doing with my writing – no matter what the project is – is finding moments of shared human experience. Things that connect us across any identity politics.
Identity politics are in my book. I try to acknowledge who I am, acknowledge my privilege. But that’s not the core of my book. The core of my book is about what makes humans the same and how we can relate to people in a different country or different school.
Through the book, I’m trying to find that empathy, that shared humanity. And I’m trying to understand what bonds us together as human beings.