Writing

Jay‑Z Re‑introduced Me to Basquiat

I have painted since I was four years old. Sketchbooks first, then canvases, then an easel that still eats my afternoons. My high school gave out two Verizon scholarships, one from the music department and one from the art department. I won both in the same year, and I was the first student there to do it.

So I did not come to art late. What I did not have was a reason to look properly.

I have thought about that pair of scholarships since. At seventeen they just looked like two prizes. Hip hop is where the two stopped being separate.

The name in the verse

I knew the name already — any kid who paints does. But Jay-Z puts Basquiat in his lyrics the way other rappers name cars, and hear it in a verse enough times and you go back and find out why. That is the whole distance between recognising a name and understanding one, and hip hop walked me across it.

“The truth is, as far as hip-hop and arts, we were like cousins. If you think about those days when Fab Five Freddy was with Madonna and Basquiat and everything.”

Jay-Z · Real Time with Bill Maher, 2013

What I found was a kid from Brooklyn who put crowns and skulls and scrawled words on a canvas and made the art world come to him. He did not wait for a door to open. He kicked it in from the outside.

That is the part that stayed. Not the prices. The nerve.

Then I bought into him

Years later, the first piece I ever invested in was a Basquiat. Not a whole painting. Shares of one, held the way you would hold a position in anything else.

I have thought about whether that changes what he means to me.

Michael Olaiya standing beside a large Basquiat painting in a gallery
The Broad, Los Angeles

My art page says I do not look at paintings as investments, and that is still true. Looking and owning are two different acts. Standing in front of the work, I am not running numbers.

But I would be lying if I said there was nothing fitting about it. A man whose entire story is about getting inside a room that was not built for him, and a generation later, people who look like him owning a piece of the room.

What the music actually did

Hip hop did not just borrow from the culture. It sent a whole generation of us to go and look.

“Concerts are pretty much performance art.”

Jay-Z · the first line of Picasso Baby: A Performance Art Film, 2013
Picasso Baby · Jay-Z at Pace Gallery, 2013 Six hours of rap, performed inside a downtown gallery — the exact collision I am describing here, filmed. This is what sending a generation to go and look actually looks like.

“When art started to become part of the galleries it became a separation between culture, and even in hip-hop people were like, art is too bourgeois… That’s what’s really exciting for me, bringing the worlds back together.”

Jay-Z · Picasso Baby: A Performance Art Film, 2013

— Mike

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