David Bowie's former painting collaborator Beezy Bailey reflects on the rock star's visual art career

While David Bowie was better known for his musical chops, the legendary rock star was a serious visual artist.

And thanks to a thrifty Canadian shopper, one of his paintings is getting a moment in the spotlight after it was picked up for $5 at the donation centre of an Ontario landfill — and is now up for auction, with the latest bid over $50,000.

But for South African artist Beezy Bailey, Bowie's history with paint brushes is old news. 

After they met during one of Bowie's trips to South Africa, the pair collaborated on more than 50 paintings in the 1990s. Bailey and Bowie remained friends until the musician's death in 2016.

Bailey spoke with Day 6 host Brent Bambury about how the friendship came to be, and what it was like painting with one of music's biggest stars. Here is part of that conversation.

You suggested that the two of you should paint while you chatted. How did Bowie react to that? 

We realized that we had quite a lot in common. You know, I said, "Did you go to art school?" And he said, "Like most rock stars, I started off at art school." And clearly it occurred to me that then he was interested in painting.

That's when I made a suggestion pretty early on that perhaps we should, instead of just sitting with the mic and a recorder, get into the studio and do some painting. He immediately loved that idea, and that's how it started.

That's a pretty bold proposal — to invite David Bowie to paint with you while you paint. How did you get that idea?

It sounds a bit weird, but I kind of clicked with the guy. So I didn't feel, "Wow, I'm taking a big chance," kind of thing. I almost felt like I was giving him a break.

I don't mean to sound arrogant, but yeah, it was like, hey, he's staying in a hotel in Cape Town. It can be quite boring, and this would be an exciting thing, which, of course, it was for him. And he immediately responded in that way very positively.

So what did you and David Bowie paint on that first visit? What did you produce?

What we did to kind of break the ice is we played what they call exquisite corpses. It's a surrealist game where you draw a head, and the other guy draws a head and you leave a mark for the neck, and then you swap papers and you draw the body, and so on down to the feet.

We did two or three of those, and in fact, we did T-shirts.... And then he scrawled on the back of the T-shirt, the first one we did, "Bound for Glory." That was what he decided to call that piece.

After that first meeting, Beezy, where you clicked, Bowie invited you to come to New York for two weeks and to paint with him. That was his program. He wanted you in the studio with him. How many paintings did the two of you finish during those two weeks?

We finished, I'd say over 50, actually. And some of them were really big. Six-by-seven-feet big. I mean some huge canvases included.

I painted, which was later on to become a theme in my work, where if you look at Christ on the cross and you remove the cross, it looks like he's dancing. But actually I got Bowie to pose in that pose, painted him against a black background life size, and he painted me in a similar position.

When you say you collaborate, I mean, obviously you posed for each other, but did you actually paint on each other's paintings?

Very much so. So what would happen is we would lay out several canvases against the walls and on the floors and we would run around going from one to the next, very much aware of a kind of 50-50 contribution to each image.

It reminds me of the scene in Basquiat, which is the film that Bowie was making at the time, where he's playing Andy Warhol and Jeffrey Wright is playing Jean-Michel Basquiat, and they are standing up and kind of collaborating on a painting in real time together. Did you think that when you saw the movie?

Absolutely. And the kind of stuff that weaves in and out here is unbelievable in terms of the kind of real life coincidences and all the rest. It's quite amazing.

You said that there's a lyric in Outside that you think may have been about you. Can you tell us about that?

[It's like] that song, "You're so vain. I bet you think the song is about you." But I just couldn't help thinking because basically he'd come in the studio and say, "Hello, spaceboy." 

And then it comes out on the album Outside, which, of course, he was working on while we were painting, the song Spaceboy. And quite a few of the lyrics in that song I can relate to possibly being about myself.

I'm not saying the song's about me. I'm saying I could have been woven into that song.

Do you think it ever bothered Bowie that he wasn't as recognized for his visual art in the way that he was for his music?

I don't think so, necessarily, for the simple reason that that wasn't his main focus, as it were.

But there was definitely, throughout the time, the kind of awareness that he lived in the shadow of his own superstardom, in terms of escaping from under being David Bowie, the rock star singer, to being a painter, which you can understand.

Imagine taking Picasso and Picasso now wants to go and start a rock group. People are going to say, "You've got to be kidding."

Written by Jason Vermes. Interview produced by Annie Bender. This Q&A has been edited for length and clarity.