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In which The Art Assignment visits Chicago-based artist Deb Sokolow and receives the assignment to do a stakeout!


1. Find an interesting object

2. Place the object in a public spot where people can interact with it

3. Pick a location to observe these interactions

4. Document your experience (photo, video, drawing, anything)

5. Upload it using #theartassignment

6. Fame and glory (your work might be in a future episode)

Learn more about Deb's work here:
Listen to a great interview with her here:

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Sarah: Hi, we're here in the scenic, warm, west town neighborhood of Chicago to visit the artist Deb Sokolow. Deb makes huge wall-sized drawings that tell elaborate stories using text diagrams and images. What makes her work so interesting is that the narratives are densely layered and blend fact and fiction. In them, she unravels complex conspiracy theories and delves into the inner and alternate lives of artists, politicians, celebrities, and even neighbors. So let's get out of this bitter cold and go see what Deb has in store for us.

Deb: I’m Deb Sokolow and this is your Art Assignment.

2003 was when I had a- sort of an art crisis. Um, and I think that had a lot to do with what was going on in the world at the time, um, of course it's post 9/11 and we're going to war and it felt, art felt like a very decadent luxury. I remember a grad school critique where there was a, someone, a faculty looked at the work and they said, "well this looks like a waste of materials." (laughs) And I must have looked outraged, but in my mind I though, ‘Yeah, isn't it? It really is a waste of materials; why am I here?'

Sarah: So Deb decided to take an art break and watch a bunch of movies instead. One of those movies was Rocky, which she related to on a deep level. Not just a boxing movie, Rocky was about going the distance and love. So she decided to map out that love story and created a nine foot long flowchart that beings as an objective account and unravels into a highly subjective tale, as she inserts herself into the story as an alternate love interest for Rocky. Like Rocky, Deb prevailed. She continued to make art, but in this new way, exploring stories and people with obsessive intensity. Paying such close attention to others that it became a kind of surveillance.

Deb: This assignment is called 'The Stakeout.' So for The Stakeout, what you're going to do is place an object or objects in a public spot, perhaps on a sidewalk somewhere, and you're going to observe that spot for as long as it takes. See if anyone picks up the object and takes it with them, or picks up the object and looks at it and then puts it back down. Record whatever happens - it could be photographs, it could be words, it could be sketches, and share your documentation.

John Green: No, no, no, no, no. This is another one with no painting!

Sarah: Oh, well, you know, Deb isn't pure social practice. I mean she does an action like this and then she goes back to her studio and she makes a drawing.

John: A drawing. Now see, like that, I understand.

Sarah: Okay, okay.

John: And I do like that this is about surveillance and very topical...

Sarah: Yeah, yeah, yeah it's extremely relevant, I mean with the NSA controversy...

John: Yeah, and it makes you into the watcher instead of the watched, which is interesting.

Sarah: Right, well, and of course there is precedent for it too.

John: Oh, I'm sure there's art historical precedence.

Sarah: Do you want to see some?

John: Of course!

Sarah: Okay. Deb's stakeout calls to mind Vito Acconci's Following Piece of 1969. Every day for a month he randomly chose a stranger on the streets of New York and followed them until they entered a private space. About it he said; "I am almost not an “I” anymore, I put myself in the service of this scheme".

There is also Sophie Calle's Suite Vénitienne, which began in Paris in 1980 when she followed and quickly lost sight of a man she spotted on the street. By chance, she later met him at a party and learned he was about to take a trip to Venice. So she donned a blonde wig and followed him there. For thirteen days Calle pursued the man throughout the city, taking photos and writing detailed reports, including thoughts like "I must not forget that I don't have any  amorous feelings towards Henri B.”

Acconci, Calle and Sokolow's stalker-like activities raise important questions about the nature of surveillance. Does this stakeout reveal more about the watcher or the watched? Is it about the clandestine thrill of spying? Or exposing the vulnerability of others? And what are limits of public and private space?

Deb: I think -uh- it might encourage people to become more observant about their surroundings. When you walk though life with your headphones on all the time and music blaring, you're missing out on whatever's going on around you. And I think that that's a big mistake. I think there's something important about, uh, paying attention to other people and about being curious.

Sarah: Okay, so here is where this idea came from: For months someone had been stealing Deb's Sunday New York Times. It's delivered to the doorstep of her building, and if she got there before 7:30 in the morning, the paper was there. It was later the paper was likely gone. Completely fed up, Deb and her boyfriend made a plan. They would stuff the previous week's copy back into the plastic sleeve, put a note on it that said "We are watching you", plant it outside the door and then watch it from the café across the street. But the morning in question they were tired, so her boyfriend ended up planting the paper but went back inside and promptly fell asleep. Someone took the paper and they didn't see who it was. The next week Deb tried again and planted another dummy paper, this time with a note that said "We now know who you are!" Well rested this time, Deb sat at the café across the street, drank coffee, watched what happened and took pictures. Two individuals stopped and looked at the paper, but neither took it and no-one has taken it since. So this made her think: she could plant anything out there and watch what happens.

Deb: And then I saw this one book, that's the very first book I ever purchased on conspiracy theories, and it's a little dictionary of conspiracy theories. And to sort of sweeten the pot, I would put in some dollar bills, kind of sticking out, just to see if that would grab attention. If no-one even looks at it, then I might go back out and move the dollar bills up, or maybe I'll just end up putting a twenty in there, if no-one really approaches it. And I don't want this to get wet. No-one wants a wet book, so I might put some cardboard underneath it. But I'm defiantly gonna prop it up on the side of the building so that it looks like someone intentionally left it there, instead of having it just flat on the sidewalk and that’s looks like someone dropped it, and I want it to look very intentional.

Deb: Uh oh, there's someone else, oh but he's gonna block it, oh oh!

Sarah: Ah, ah.

Deb: Oh OH! How great is this? Oh finally! Finally! Oh!

(Both Deb and Sarah are sighing, oh-ing and laughing)

Deb: Running… He's noticing it, he's noticing it! He's not going for it.

Is it time to put the twenty in?

Sarah: The twenty?

Deb: Yeah... Kitty, what are you doing? What do you think miss kitty?

Sarah: Here comes a couple guys. Uh, oh oh, somebody-, come over, come over. This guy, this guy right here.

Deb: This guy?

Sarah: Yeah, he passed it, now he's coming back.

Deb: Aha aha, oh! (laughs)

Deb: I would have hoped that there would be a little something more that would have happened. I think it would be great if two people picked up the book together, and maybe there would have been a conversation about that, so I'm a little bit disappointed, but I'm also really happy that someone took it. And I  think it's really interesting that he took it not too long after I put the twenty in. And I did bookmark the bills, the bills were bookmarking certain conspiracy theories in the book, so I was a little bummed that the guy who took ended up taking the book and the money, took the money right out of the book right away and didn't see what was bookmarked. Now I miss the book. I wish I had that book back.


Deb: Did I do it right? Ah, okay, awesome, are you gonna put that in?