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The performance poet-turned-rapper Watsky pulled no punches in his first collection of essays. All of his work is characterized by witty wordplay and disarming honesty.

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Watsky is a slam poet turned rapper known for his fast-paced vocal delivery and versatile lyrics.

Born as George Watsky in San Francisco in 1986, he won several slam poetry competitions as a teenager and placed fourth in the National Youth Poetry Slam in 2006. He recorded his first hip-hop album in 2009 after graduating from Emerson College in Boston, Massachusetts. In 2011, his humorous video “Pale Kid Raps Fast” became a viral phenomenon, garnering over 25 million views. His 2013 album Cardboard Castles topped the iTunes hip hop charts. His next record, All You Can Do (2014) peaked at number 33 on the Billboard top 100. He released his sixth studio album, Placement, in 2020.

In May 2020, during the COVID lockdown, Watsky rapped consecutively for 33 hours, 33 minutes, and 19 seconds, setting the world record for the longest continuous freestyle rap and raising over $140,000 for artists affected by the pandemic. He published a book of essays, How to Ruin Everything, in 2016.


After winning several high profile slam poetry competitions, a teenage George Watsky became a spoken word star.

There’s 7,046,000,000 people on the planet and

most of us have the audacity to think we matter.

Hey! Hear the one about the comedian who croaked?

They stabbed him in the heart, just a little poke.

But he keeled over because he went into battle

wearing chain mail made of jokes.

Hey! Hear the one about the screenwriter who passed away?

He was getting elevator pitches and the elevator got stuck halfway.

He ended up eating smushed sandwiches they pushed through a crack in the door

and repeating the same crappy screenplay idea about talking dogs till his last day.

But after years performing on the college circuit, his attention shifted to another art form. But he says that, far from a radical shift, becoming a rapper was merely an acknowledgment of his first love, live music.

George Watsky: That was my version of going to church, was going to a concert and seeing those people up on stage and the energy of the crowd. The experience of a concert is something that is extremely special to me and to be able to do it on a nightly basis, it’s this crazy rush. I get to be the most ego-driven version of myself on stage. Which allows me, I think, to be a little shyer in private life. Whereas in the past I thought I needed to be the center of attention all the time. Because I had no other outlet to fuel that part of me.

Even as he plays an exaggerated version of himself on stage, Watsky remains steadfast in his commitment to his own voice, rather than a pale imitation of how tradition dictates a rapper should sound.

Watsky: There’s a lot of politics involved in being a white rapper. There’s a lot of conscious and subconscious choices you make about how you want to be perceived as a musician. And those choices actually say a good deal about where you stand as an MC, what you think about hip hop and your place in hip hop. And for me, one reason that I fell in love with hip hop is its honesty and the person who is speaking, relaying their own experiences. For me, my experiences are going to be the ones I’m having talking to you. And yeah, some people when they listen to me might not think it’s their idea of what rap is supposed to sound like or what classic hip hop is or what they grew up on loving. But what I grew up loving was honesty, perspective, sharing yourself. And so that is my conscious choice when I rap, to sound like I sound in conversation. And some people might perceive it as being nerdy or like “Wow, that guy sounds really white.” Like, yeah okay, I am. That’s who I am, that’s what it’s gonna be like when you meet me.

Watsky’s music draws from a wide swathe of influences, including, unusually, classical music. His latest album, x Infinity, ends with a song cycle.

Watsky: The first one is a song called “Conversations”, which is about two different conversations I had with my father about mortality. One when I was nine and about to turn 10 and one when I was 29 and about to turn 30. And in the first one, my dad was consoling me because I was freaking out about getting older, that death isn’t for a long time. And in the second conversation, I was consoling my father that it wasn’t for a long time. So the first verse is his conversation to me and the second verse is my conversation to him. That goes smoothly into “Knots,” which is sort of a Chopin inspired piano piece that I rap over, and it tells the story of a piano player named Arthur Rubenstein. He attempted suicide when he was young. He was in his early 20s. So he tried to hang himself and his rope snapped. And he felt that he had an epiphany at that moment and “Knots” tells the story of Arthur in his room with creditors banging at the door as he ties the noose, he puts himself up on the chair and then steps off it. “Knots” ends with him stepping off of the chair.

Watsky regards himself as a writer first and foremost. His debut collection of essays published by Penguin Random House is a New York Times bestseller. How to Ruin Everything is a brutally honest recollection of some of the most memorable episodes of his life so far. “Ask Me What I’m Doing Tonight” recounts his time as a traveling poet.

Watsky: And I’d learned after this many shows that any single performance can be the one that inflates your ego or destroys it. The night that makes you feel like a big web of energy links every single being across time and space. Or the gig that alienates you from every shallow, shitty human on the planet. After the show, I rolled around in a field with a pretty redheaded agricultural engineering student like I got to do occasionally after good shows. We pulled ourselves apart, laid on our backs looking up at the quilt of stars, hundreds of miles from the light pollution of St. Louis. Am I going to see you again? Yes. I never really gave much thought to the fields while flying over them. Just seems like a whole lot of empty space from above. But I wonder how many half naked kids you’d see rolling around in them if you zoomed in. Back at the Super 8, I scraped the golden crusty cheese off the corner of my Stouffer’s container with a plastic fork I picked up at the front desk. The corners are the best part and I always save them for last. “Maybe I’ll start eating better on the road”, I thought, and check the ingredients on the back of the Stouffer’s box. “Wheat. But maybe later.”

These days, Watsky is a world away from the college circuit and so too are his lyrics.

Gotta shovel, now I’m breakin’ this ground.

Because I’m in the red

but it’s only a color that I will be paintin’ this town.

Because when I make it, then I dedicate it to the

friends that stood with, who would do me favors.

Even lend me paper, when I couldn’t pay for

A little take-out.

Watsky: I’m trying to do self-examination and I’m trying to meditate on what I really think. And when there’s a world event, I do try and go deeper into the layers of what I think. Doesn’t mean I’m always giving the most intelligent analysis of a situation. But I am trying to at least examine what I really think about stuff and play the counterargument against myself.

AJC: Right, but aside from external events, you’re going through this world. You’re a person on this earth and you’re changing and growing all the time, and having new experiences in your relationships to other people and in your relationship to the world. How much of that self-examination goes into your music, do you think?

Watsky: I mean, a confusion and a terror about living and mortality has always been the driving force behind all my work. And if there’s anything that I’m trying to get across, it’s how little I know, how much I think that a person to exist in this world needs to rationalize their existence just to get through a day. And you know, we don’t even know what we are and yet we’re able to stumble our way through life and through a week and through a month. And yet, under the surface, at least for me, in every moment there’s this feeling of like “What is going on?” at all times. Like I know as you get older, you get better at pushing those thoughts to the back of your mind. But I don’t wanna get better at pushing those thoughts to the back of my mind. I think that even though you’re growing older and getting better at existing, you’re also getting worse at examining and seeing wonder in things and realizing how bizarre daily life really is.

Bouncing off my bedroom walls since I was hecka small

We’re every age at once and tucked inside ourselves

Like Russian nesting dolls

My mother is an eight year old girl

My grandson is a 74 year old retiree

Whose kidneys just failed

And that is the glue

between me and you

That is the screws and nails

We live in a house

made of each other

And if that sounds strange

It’s because it is

Somebody please freeze

time so I can run around

Turning everyone’s

pockets inside out

And remember,

you didn’t see s–t

Watsky: I think that there’s a hypocrisy in what I do, which is at the core of my work, I’m sort of a nihilist. I don’t believe in fate. I don’t believe in a structured god. I don’t believe that there’s a plan for me. I’m terrified of not mattering. I know that I don’t matter. Like every individual human being is a grain of sand. But yet I want to so much. I want to matter, I want my work to matter, I want to communicate with people. I want to connect with human beings. I want my life to feel like it has meaning on this planet. I believe in beauty even though I don’t know what it is and yet… It’s the core message of my new album that nothing matters, so it doesn’t matter, nothing matters. How do you square up the fact if you are a nihilistic person and believe that we’re all just dust in the wind with the fact that you want to live a meaningful life?

And for Watsky, meaning lives here.

So when the world breaks your legs

You go and beat it with your crutch.