When confronted by the press about Chicago’s overwhelming political corruption, city politicians often shrug and curtly concede: “That’s Chicago politics.” The city’s corruption is so native and unyielding that it just “is what it is,” has been and always will be. In Steve James’ five-part docuseries City So Real, a buoyant portrait of Chicago loosely wrapped around the 2019 mayoral election and the murder trial of Chicago police officer Jason Van Dyke, the city’s denizens justify an array of their problems with that same self-referential and self-enabling sentiment, “That’s just Chicago for you.” But the city’s 2019 mayoral election saw young candidates on the ballot give voice to a growing want and need for radical change. James spent time filming candidates like Amara Enyia, Ja’Mal Green, Neil Sales Griffin and Lori Lightfoot, despite their being at the very bottom of the polls. Of course, in a major upset, Lightfoot went on to win the runoff election over Toni Preckwinkle by a landslide. Under Lightfoot, Chicago’s status quo didn’t budge, but the global pandemic and murder of George Floyd finally gave the dogged city a shake.

By now, everyone knows the results of the election and trial (Jason Van Dyke was sentenced to just six years in prison for the murder of Laquan McDonald). James doesn’t generate pseudo-suspense around these past events and instead lets his lighter humanist fascinations guide him. As we know from his past work, his lens knows no racial boundaries. In City So Real he finds himself on the predominantly Black south and west sides as often as he does the predominantly white north side, and majority Latinx east side. The impressionistic structure of City So Real, coupled with the extended length of the docuseries (he was always limited by the standard duration of the feature length documentary) sees James perusing Chicago at his most liberated and, to our amusement, undisciplined. 

But, over the years, the thought of a white filmmaker imposing his camera on non-white communities has become more contentious. What happens when a “white camera” starts rolling on Black, yellow and brown subjects? Are the white filmmaker’s motivations pure and even then, is their camera not susceptible to implicit bias? Are its BIPOC subjects not reduced to how they react to a white camera and white audience? In early September 2020—as Steve James was still shooting footage for the fifth and final episode of City So Real—he took a break from wrapping his finale to conscientiously reflect on his role as a white filmmaker with creative liberties in non-white spaces, and how he goes about embracing his access to subjects or lackthereof. City So Real premieres tonight on National Geographic.

Filmmaker: I didn’t realize you were still shooting footage for the final episode of City So Real.

James: When the pandemic hit everything shut down. Lori Lightfoot was gaining a national profile, and since we hadn’t sold the series yet, I thought it would be great to do some kind of postscript that takes account of the pandemic. Then, when George Floyd hit and the upheaval, it became clear that we needed to do a full-on episode. Then I was out in the streets a lot more. Before that I was doing internet interviews with people from my home and shooting very minimally. I’m excited about the prospects of this episode—it will certainly make the series even more relevant. 

Filmaker: I’m always curious about how and when a documentarian chooses to end their films when the story they capture is a continuous one and there are always potential milestones on the horizon.

James: Originally it was going to be a standalone film, then that changed. If you talked to people I work with, they’d tell you I have a problem about shooting too much. There was so much going on that it became clear it really wanted to be a docuseries. My partners at Participant [Media] were very supportive of that. The concept was that we would shoot through at least the first election and possibly through the runoffs. But once we got through the first part of the election I felt there was no way we could also put viewers through a deep dive of the runoff. [laughs] I figured people would be like, “Please, don’t do that to me.”

We shot some between the first round and the runoff, but we were very strategic with that plan and thought that was the movie. Lori came from nowhere and, as it turns out, becomes the mayor of Chicago. That had a neat conclusion and I was perfectly happy with that until everything else happened. So, now I’m really excited about the idea of getting to look at what it means for the city right now. The city is certainly emblematic of what’s going on everywhere else. 

My filmmaker friend Robert Greene said I should just keep just keep shooting. At some point we’d have 20 episodes. If someone was willing to pay for that I would probably consider it! [laughs] 

Filmmaker: How flexible is a documentary budget to an extension like that?

James: I’m a real bargain as a filmmaker. We had to make some allowances for the larger length, but it wasn’t expanding the budget in any significant way. We shot a lot and there was a lot to cut. I have a terrific co-editor in David Simpson, who I’ve worked with a lot over the years. One of the reasons docuseries are becoming so commonplace and prevalent is because the economics of the docuseries work so well for sales. To be able to give a streamer or a network multiple hours of content—I’ve been making long films my whole life, so I was made for this. [laughs] Or I’ve been enabled by it. But there’s an economic logic to the docuseries that works, as well as the fact that it allows you to dive much deeper into a topic. 

Filmmaker: And they have an easier time selling than a three-plus-hour documentary.

James: Absolutely. I had gotten away with making long films, but if you look at the majority of standalone documentaries, there seems to be a consensus that 90 minutes is the length a documentary needs to be. It’s rare to see one that’s two hours, that’s considered long now. 90 minutes is the sweet spot and I think filmmakers know that and that’s what buyers are looking for. It will make people more inclined to consider their film. [Buyers] look at two things, the description of a film and how long it is. [laughs]

Filmmaker: Have you found your truest form in the docuseries format?

James: Yeah. If I was making Hoop Dreams today it would be a docuseries. No one wants to show a three-hour documentary in a theater, period. We were extremely fortunate that that film played theatrically at a time when theaters played few documentaries theatrically, it was kind of astounding. These days that wouldn’t happen. I think of City So Real as basically a five-hour documentary that’s been broken up into episodes. It doesn’t conform to the docuseries style that a lot of these crime documentaries do.

Filmmaker: The cliffhanger.

James: Yeah, and withholding information. The little twist at the end of the episode to make you keep watching. There’s an art to that, but that’s not what this series is, that’s not what America To Me was. I’ve always done long films. Now I get to make them even longer and in a form that’s more commercially viable and valuable to audiences.

Filmmaker: Each episode does have a unique ending unlike a feature-length film, though. The end of the first episode: Maze Jackson closing the WVON 1690 AM morning show with the haunting sound of 16 gunshots in succession, a moment to reflect on the murder of Laquan McDonald by CPD officer Jason Van Dyke. The gun shot sounds seem to go on forever. Another episode ends abruptly to match an abruptly ended debate between the mayoral candidates at the Chicago Sun-Times. They’re not your usual episodic endings, so what was your approach to them?

James: You do want to think through how you begin and end every episode, because people are fickle. They may love the previous episode, but if the next episode doesn’t grab them they have plenty of options out there. [laughs] So, you do want to grab people at the beginning of each episode and lead them to a strong, provocative ending. Even if it’s not the traditional cliffhanger, at least they’re in a place where they want to keep watching. So that 16 shot scene seemed like the perfect ending to episode one. Much was made of the Laquan McDonald trial in Chicago and without question “16 shots” became the catchphrase for the tragedy. So the way Maze Jackson, the radio host, would play that was haunting. It’s episode three that the debate happens. The debate is so funny and contentious that it seemed like a great way to go out. We’re doing something with the series where we have the title come in at the beginning and at the end, so we’re also thinking about that too. What leads us back to the title of the series that resonates? 

Filmmaker: Unlike America To Me or some of your past work where you filmed people who are not used to being under a movie camera’s scrutiny, you’re filming mayoral candidates on City So Real who are. These people are always “on.” Was there an impetus to crack at that armor? 

James: There were two things I knew going in. We weren’t going to embed with one or two candidates completely and tell the story of the election through them. I didn’t want to do that. That’s a lot of political documentaries that follow campaigns. Lately there’s been this thing, like with the AOC doc and some others, where people are following multiple candidates in completely different races. I love the idea that there were ultimately 14 people on the ballot who represented this wide array of people who thought they could be the mayor of Chicago. [laughs] On the other hand, I knew that we weren’t going to be following 14 candidates either. We were going to have to make some choices, so we felt our way into it. Certain candidates were much more willing to allow us to film them and some candidates weren’t willing to let us in at all, even though they are in the film. Toni Preckwinkle, for example, we went to events and just filmed her. We never got inside her office or inside a car with her, but that doesn’t mean she’s not in the film—and probably not in ways she’ll be crazy about. 

But there were certain candidates, like Lori Lightfoot, who really interested me from the beginning, even when no one was giving her a shot at being mayor. Here was this woman who had never run for office before, a gay Black woman with a strong personality. I let my fascination drive that. In the same way, Neil Sales Griffin, who literally came in last, is one of the most prominent people in the series because there was something about him that fascinated me. Amara Enyia was another example.

Then there were candidates that I really wanted to get access to like [Bill] Daley, Susana [Mendoza], and Preckwinkle. But the candidates who thought they had a serious shot at winning were not going to let us in. I’m sure part of the calculus was, if they won and there was something embarrassing in this film about them, they’d regret it. And obviously we weren’t going to help them get elected. We weren’t media. It was always interesting when we’d try to initiate with these candidates and they’d see me with the big camera and go, “Oh who are you with?” They were very interested, but as soon as I gave them my pitch they were like, “Oh yeah, talk to my press people!” and it would go nowhere. We probably shot enough to make a whole film on Amara Enyia. She was one of the candidates who was the most receptive. But I knew we weren’t going to do that. For Lori, we had to overcome her press people to get the footage that we got. She personally liked the idea of what we were doing and liked us, but her press people didn’t see any value in it for her. So we really had to work around them to get what we got, and thank god we did, because she won. 

Filmmaker: Lori becomes more prominent in the series in the same way she does the election. Did that have to do with access or editing choices?

James: It’s a combination. We were certainly filming all our main people down the stretch. The press people would never cooperate with us—after one initial shoot with Lori they were done with us. But Lori really appreciated what the film was about. I told her we were following the campaign, but that we were also following the trial, that it would be a mosaic portrait of the city itself and the people who live here. We would just show up and walk straight up to her, bypassing her press people, and say, “Hey Lori, do you mind if we put a mic on you today and shoot a little bit with you?” Before her press person could get in the way or intercede, Lori’d often say, “Sure!” [laughs] I’d get a look from the press person, but the boss had said yes.

Both myself and Zak Piper, my producing partner of many years who played a vital role, felt she was coming on. We didn’t necessarily think she’d win, but that Sun-Times endorsement shocked everyone. I mean, the Tribune endorsed Daley. [laughs] You’d expect the Sun-Times to endorse someone like Preckwinkle, or someone who was thought of as having a real chance to win, but they bravely went with Lori. At the time they endorsed her she was 2.8% in the polls. That was huge. That got everyone’s attention. So, we redoubled our efforts down the stretch. Fortunately it paid off.

Filmmaker: It’s interesting that candidates like Daley hear “documentary,” rather than a news outlet, and feel it’s something to avoid. 

James: One of Daley’s people, I won’t say who —and this is a guy who liked the idea of doing this—told me, “Bill’s not really good with people.” [laughs] “He worries about how he’ll come off.” Of course I’m like, “Oh no, it’ll be fine!” But I’m thinking, “This guy wants to be mayor and he’s not good with people?” [laughs] But it didn’t stop us from featuring him in the film and I think not having access to those larger candidates ended up being a blessing in a way. It didn’t mean that we weren’t going to find a way to reveal them in the film, but it also allowed us to focus our energies on candidates who I think are probably more interesting. I hope this is not a film that comes off as, “Who is going to win the mayoral election?”  It’s not this heavy, plot-driven film about election and strategy. I’ve seen plenty of great documentaries that do that, but I wasn’t interested in doing that. I was interested in using the mayoral election as a spine to a film that was much more a portrait of the city, and the wide array of candidates represents the diversity of people in the city. 

Filmmaker: You build your transitions through the city. You’ll have shots from inside a bar or a salon with news on the TV and cut to the actual footage and out to somewhere else from there.  Can you talk about how you made your way through your portrait of the city?

James: The inspiration for this film was the Chris Marker film Le Joli Mai, which I saw in grad school thirty-however many years ago. At that point in time I was probably more wanting to be a narrative filmmaker, but this really turned my head around to documentary. It’s a portrait of Paris in the mid ’60s and it’s one of those liberated films in the way that it has a little bit of everything. It’s a kitchen sink film: it has verite scenes, scenes where he just talks to people, poetic passages that look like Cartier-Bresson photographs of Paris, this poetic voiceover that I knew better to try to attempt. I remember seeing it and thinking a documentary could be anything. After being in Chicago for a number of years I kept thinking it’d be great to attempt something like that in Chicago. He found a kind of perfect moment when politics were coming out, Algeria was very much on people’s minds. I always knew that if you want to [make a portrait of a city] that you don’t just do it randomly, you hang it on something. 

When this mayoral election came along and it was coinciding with the Laquan McDonald trial I knew it was the time to do it. Zak and I and my son Jackson, who was also very prominent in shooting the film, really wanted serendipity to drive where we went. We knew we had the mayoral election as a spine, but beyond that we wanted to let the stories literally take us where we’d go. There were many days that we went out and maybe had one thing in mind to shoot and had no idea what else we’d shoot and just winged it. We met people: the shoe shine guy, the Uber driver, the couple that did the early voting.

In the past, if you come across interesting people like that and they’re not part of the story you’re telling, you don’t make them part of the film. [laughs] But this was a film where we could do that. We had captured some of that news media in situations, which was good, it was inside the idea, but then we thought we’d go and shoot televisions all around the city so that we can show the city instead of having boring news media full frame. It’s another element of what the city looks like. In post we started going out and shooting places wherever we found televisions. [laughs] Then we [composited] news media on to some of the televisions. So it was a combination of actual sound in the place, but also orchestrated, which is a lie, but one I’m very comfortable with. 

Filmmaker: It also leaves room for comedy. There’s the Willie Wilson supporter who can’t pitch a sign in the ground, the squirrel running off with a Reese’s Peanut Butter Cup. 

James: A lot of times people think of my work as just tackling serious issues, which I do. But most of the films I’ve made are pretty damn funny. Even The Interrupters is funny—it’s not just funny, but there are funny moments. Myself and the folks I’ve worked with over the years have always had an eye out for something that makes us laugh, both in the field shooting and in editing to bring that forward. Even though these are long films, I want them to pull you through them with a range of emotions. When you’re making a film like this, which is pretty random [laughs] in a lot of ways, what’s going to pull you through it as a viewer? There’s a lot going on in Chicago and it’s also profoundly entertaining. Politically, it’s arguably the most entertaining city in the country. [laughs] 

Filmmaker: You randomly swoop in on a dog walker who invites you and the film crew into the houses of people like a circuit court judge who lives in the Gold Coast neighborhood. Did you need any other permission to get in, or was it free reign after getting the dog walker’s go ahead? 

James: [laughs] That was, of course, Participant’s first question when they watched it. “We love this scene, but oh my god, did you have permission to be in those people’s houses?” Yes, the dog walker got permission. He explained what we were doing and they gave us permission, so that was a great relief to the people at Participant. 

Filmmaker: You’ve said before that you used to be asked how, as a white filmmaker, you made Hoop Dreams, and that the question has recently turned into should you be telling Black stories as a white filmmaker? I’ve noticed that one of the effects of putting BIPOC people in front of a white camera-person is that they begin to talk, even in casual conversation with others, as if they’re talking to or explaining something to a white audience they wouldn’t have to a non-white filmmaker. What you’re capturing becomes a response to the white perspective. It is not only that, of course, but what’s your approach? Do you always aim to close the gap between you and BIPOC subjects or does that distance sometimes make sense?

James: Right, that’s a complex question. Let me start by saying, even though the principals in this film are white, we had a very diverse team. We had two Black field producers, our third DP Kevin Shaw and our sound person Baili [Martin], who did the most of the sound besides Zak, are Black. So, I was very conscious of having a diverse team in the field because it is vitally important in telling these stories. I feel that responsibility and need more than ever. America To Me was very much in that mode. But I think you’re right, and it’s not necessarily a bad thing. You’ll have to decide if it falls into that category you describe, but I feel like there are absolutely moments as a filmmaker, if I put in the time and developed relationships with the subjects, that I’m getting something that doesn’t necessarily feel directed at me as a white person. The scene in the Black barbershop, Kevin Shaw shot and Bailey recorded. I was there, but I had a Black team in place and think that it helped the situation to evolve in the way it did, which was that conversation [between a barber and a customer]. To me, it is an utterly vital conversation those guys are having.

Over the years I’ve been able to in some ways, not overcome, but get to a place where there’s a level of comfort and trust where the subjects are presenting themselves more authentically—in the way they would in the world. Having said that, I also think there’s plenty of times where what you’re saying is true. Black subjects want to be heard. It’s not so much an agenda they want to put out. They are explaining to me, as a white filmmaker, outsider, something vitally important to them and they are articulating it in a way for me to really get it, and by extension, frankly, most of the audience. Because most of the audience for all of these films are white—although it’s changing, which is great. I think of myself as a filmmaker who, when I go in and tell stories in communities of color, is trying to understand, capture, learn and humble myself—realize I know nothing. I am white, and I am white in that situation. I would say that for many of my films the initial audience is absolutely white, because I am their surrogate in a sense. But what pleases me, I have to say, is that certain films I’ve made in those communities have also been embraced by those communities. The Interrupters was, Hoop Dreams was, and America To Me has been embraced by people of color, especially people focused on equity and race in the educational space.  

Those are due to not just to me, but the team in place and the time we put in to tell those stories. We’re not swooping in to get an opinion or get a quick take. For me, a perfect example is Flamo [from The Interrupters]. There’s a scene where Kobe takes Flamo to get some jerk chicken and it’s a funny scene because he’s trying to smoke weed in the car and Kobe’s like, “You can’t do that!” But later in that scene Flamo talks about wanting to change his life. He very poetically says something along the lines of him wanting to be the person telling the story, not the person someone’s telling the story about, meaning that he’s dead and gone. The way he says that is so beautiful and poetic and my guess is that it would not have happened if I wasn’t there. He wouldn’t say that to Kobe. Kobe knows that. That’s not a conversation he and Kobe need to have. But he wanted to express that to me. He’s finding a way to express that to someone he thinks needs to hear it. And I feel like that’s where being an outsider can be used to your advantage, because everything is new to you enough, and if people trust you enough, fully and deeply, there’s much truth to be gained from that. 

Filmmaker: How do you convince people that you’re not that news media camera, or that camera that’s come to be used against them?

James: It’s interesting because sometimes people do think we’re that. Ameena Matthews from The Interrupters initially did not want to participate in the film. We had her boss call her to ask if she’d let us catch her on a mediation and do a little interview. She said OK, and after she was ready to bail. It took her a while to want to be a part of the film. One of the ways I convinced her is by showing her three of my other films. When she watched them she sort of got what I was doing and explained that she thought we were just typical white media people trying to get crazy shit going on in the neighborhoods. 

Even though I said all of the right things, I think, she didn’t trust me because I was white and had a camera. But the big camera can also be an advantage. It was on The Interrupters and on City So Real, it makes a statement that you’re real. Everyone’s out there shooting stuff. Everyone’s got their cell phone, everything is documented that’s at all contentious. So, if we show up and do not look like or do not present ourselves in any way that the TV media do, it can also become an advantage. On The Interrupters, we had an incident where the cops were going to arrest interrupter Cobe Williams and me and Zak because they thought we were doing some kind of scam. I went and got the camera out of the trunk of the car, because we weren’t filming at that particular moment, and he was like, “What’s going on here?” I told him, “We’re doing this documentary that’s going to be on Frontline and if you’re going to haul us in we’re going to film it.” He of course disappeared, then one of the interrupters that was with us said, “That camera’s more powerful than an AK.” 

Filmmaker: On the other hand, as a white filmmaker, white subjects feel comfortable expressing their racist attitudes to you. How do you approach them? 

James: One of the things that have become crystal clear to me, really starting with a film I did in 2009 for “30 for 30,” No Crossover: The Trial Of Allen Iverson, was that if I was going to be dealing with race in any sort of substantive way, I increasingly have to turn the cameras on white people. It was also made crystal clear to me on America To Me when [former assistant principal] Chala Holland told me that I have to film white students, I can’t just focus on students of color. So on City So Real, from the get go, we knew we were not just going to be filming in communities of color. We need to find our way into the white community and gauge who they are. The scene in the Bridgeport barbershop, we had arranged to shoot there and they were friendly to let us in, but I had no idea a bunch of them were ex-cops. We just thought this would be a good contrast to the Sideline barbershop.

We often did that. If we were going to see a white neighborhood trick-or-treating, we also went to a Black neighborhood. We wanted to show the range of experiences around similar settings or events across the city. We got a great scene in a Black barbershop—what goes on in a white barbershop? In the way that you find out in the scene that they’re ex-cops, that’s exactly how it happened for us too. It preserved that. When he tells that racist joke it takes a turn. We went to that Black barbershop in episode five after they reopened the barbershop after three months of quarantine and it was right on the heels of the rioting. Look, [the white barbers] aren’t bad people, but they have certain attitudes. The other scene that takes place in that home during the debate is one my son Jackson shot. I was shooting at the debate, but we got Gary McCarthy’s campaign to allow us to go to one of their big supporters homes. 

After the debate ended I got a text from Jackson—that scene took place in Bridgeport as well—and he texted me, “Bridgeport. Bridgeport. Wow.” [laughs] Honestly, that’s how people feel and that needs to get out there. We haven’t at all betrayed a trust. There’s a reason we include the line where someone goes, “You realize you’re on camera?” and the guy [who made several racist comments about mayoral candidate Amara Enyia throughout the debate] goes, “Yeah. I don’t care.” It’s important that you know that he feels very proud of his point of view here. People like you and me will look at that and think “Jesus.” But there are plenty of people out there that feel that way. We’re seeing that now.