For everyone else at Daley’s Restaurant that cold December morning, it was business as usual. The waitstaff took orders from customers. The cooks grabbed tickets off the carousel. A mayoral candidate, Paul Vallas, posted up at a large table, ready to discuss the issues, while his hustling senior campaign advisor Phillip A. Bradley enticed potential voters with free coffee and pink t-shirts. A woman adorned in seasonal green sang Christmas carols to smiling, if discomfited, guests.
But a father and son saw opportunity.
“This campaign manager, we started filming him, and he’s like, ‘Paul’s going to win. Paul’s going to win’ — then he just starts going,” remembered “City So Real” cinematographer Jackson James. “[He] was just so magnetic. He was running around on the sidewalk, and you’ll turn around, and he’d be inside talking to someone else. Then he was running to his car to get t-shirts to give to people. And then you’d look over at Paul, and it’d be a very polite conversation. There’d just be people talking about politics. [Phillip] would sit down for a second, take a bunch of photos, then jump up and run away again. And you’re just like, ‘Of course we’re going to go film this guy.’”
Director, fellow cinematographer, and Jackson’s father, Steve James, was supposed to be there that morning, too. His wife and Jackson’s mom, Judy, was having minor surgery, and Steve took her to the doctor. But as would often happen throughout the documentary series’ 20-month shoot, the two filmmakers briefed each other on what the other was missing.
“My dad just texted me, and was like, ‘How’s it going?’ and I was like, ‘This is crazy. Like, this is definitely going in [the series],’” Jackson said. “He immediately came down.”
So Steve, Jackson, and series’ producer and sound recordist Zak Piper sat down to have lunch, right there at Daley’s historic diner. Jackson knew Steve wanted nothing more than to join them.
“He could see how much I really wanted to be there,” Steve said, “And he so nicely said to me, ‘Do you want me to go pick Mom up when her surgery is over?’ And I was like, ‘You’d do that?’ and he said, ‘I’ve had a lot of fun with this. Yes, I’ll go get her. You film for a while.’”
Passing the torch from son to father isn’t the way that metaphor would typically go, but “City So Real” isn’t the end or the beginning of either artist; it’s an evolution, a shared vision between the pair that served as a learning experience for both. Not only a portrait of a city but of the people who bring it to life, the Emmy-nominated docuseries speaks to national issues as well as it addresses personal passions. Shots of gleaming skyscrapers and passenger-seat confessionals blend seamlessly into an intricate story that travels from neighborhood to neighborhood, candidate to candidate, scene to scene, helping the audience see the city — and thus the country — from a dizzying array of perspectives.
All of these subjects were captured by Jackson and Steve James, a family team working in the father’s adopted city and the son’s backyard. Jackson grew up in Oak Park, IL, a 30-minute train ride from downtown Chicago and the site of Steve’s last documentary series, “America to Me,” which examined racial, economic, and class issues affecting Jackson’s former high school (as well as the country at large).
Examining universal issues through meticulous personal portraits is a theme of Steve James’ work dating back to “Hoop Dreams,” making “City So Real” a natural extension of his interests. Long simmering in his mind and inspired by Chris Marker’s 1963 French documentary “Le Joli Mai” (“The Lovely Month of May”), James knew he’d have to approach this project differently.
“It was one of the films that made me interested in documentary because [of its] incredibly eclectic approach,” he said. “It has vérité moments, it has interview moments, it has poetic composition moments, it has voiceover narration that’s also very poetic.”
Before production on “City So Real” began, Steve showed Marker’s film to Jackson, Piper, and more collaborators to better illustrate the open approach to shooting he hoped to execute. Jackson remembered seeing parallels to Richard Linklater’s scripted feature “Slacker,” which bounces from character to character over the course of one day in Austin, TX. Steve encouraged the comparison, “But I think he was just saying that to get me in,” Jackson said.
“You’d see [those movies], and you’re like, ‘Wow, there’s a lot you can do with making a movie that isn’t really, necessarily, what you start off thinking you’re going to do,’” Jackson added. “The free-ness of those two movies, I think, were things that I really enjoyed.”
Watch how Steve James and Jackson James unpacked favorite films from Chris Marker and Richard Linklater to help free their approach to “City So Real” in the video below.
Steve had two ongoing stories he knew would form a throughline for “City So Real”: the 2019 mayoral election, which featured more than dozen candidates competing for Rahm Emmanuel’s vacated seat, and the LaQuan McDonald’s murder trial. McDonald, a Black teenager from the city’s West side, was shot 16 times while walking away from Chicago police officer Jason Van Dyke.
While producers would assign various events to cover — including press conferences, debates, marches, and more — Steve wanted to let chance encounters and the team’s instincts dictate what other viewpoints informed the series.
“At first it was a little maddening, because as free as I am as a filmmaker in terms of my approach, this was a whole different level of just giving yourself over to the day and where things would lead,” Steve said. “It took a while to really get into that style and feel OK with it. It’s like flying without a net in some ways, but once we did, it was incredibly exhilarating.”
The approach was part of what lured Jackson on board, since documentaries aren’t his sole focus. In middle school, he would make action movie parodies (Steve remembered a particularly hilarious entry titled “Final Paycheck”), and while attending Columbia College in Chicago, Jackson recalled getting “a very bad grade in cinematography class” because he used the designated film equipment to shoot music videos instead. Despite not fooling his teachers, Jackson’s work led to Weird Life Films, a “directors collective”/production house formed with business partners Ryan Ohm and Laura Gordon.
Before “City So Real,” Jackson’s work with his father was “more like assisting,” he said. Jackson provided additional camera work on “The Interrupters” (2011), “Abacus: Small Enough to Jail” (2016), and “America to Me,” while helming the second camera for “Life Itself” in 2014.
“Participating in my dad’s films has been something I’ve been doing for a long time, but [‘City So Real’] was the first time where we were talking about things from the beginning, as more of a collaboration,” Jackson said.
Collaborations work both ways, so while Jackson was being pulled deeper into documentary filmmaking, Steve was letting go. Typically, the director, cinematographer, producer, and editor shoots everything himself. If he wasn’t behind the camera, he still accompanied his cinematographers whenever they were filming; he always wanted to be on the scene to ask questions, guide the camera, or simply see for himself what was going on.
“His early films like ‘Hoop Dreams,’ he didn’t shoot,” said Gordon Quinn, the artistic director and founding member of Kartemquin Films, who’s been working with James for three decades. “I think gradually over the years, he came to see that he needed to start shooting his own films. He’s always on the set. He’s always there. He’s not going to not be there.”
“That’s how we saw filmmaking,” Quinn said. “We saw ourselves as filmmaker-directors, shooter-directors. But the camera, and the relationship of the camera to its subject, was critical.”
That relationship shifted on “City So Real.”
“Jackson often went out on his own,” Steve said. “There were times when he was with me and Zak, where it would be the three of us, but it became clear really quickly that it would be great for the project and for him to just let him go.”
Like the series itself, that trust took time. At first, Steve remembered being very hands-on with Jackson.
“We kind of joke about it, [but] I could tell that I was bugging him because I would be lifting his earbud out to whisper something to him,” Steve said. “It’s not that he doesn’t want direction, but oftentimes he’d be like, ‘Yes, I got that already.’”
But as production continued — from the end of 2018 through mid-2019, then starting up again in early 2020 to include the pandemic and Black Lives Matter protests — the director and parent learned to let go a bit. Piper and Steve credit Jackson for numerous memorable discoveries that made the final cut: There’s the Lyft driver in a Care Bears onesie who’s brought to tears by a racist memory; a friend of Jackson’s who walked dogs for well-off Gold Coast residents; and then there’s a fraught conflict between local police and protesters of George Floyd’s murder.
“Jackson shot that by himself,” Piper said. “All by himself. He was just out there. The instincts that were on display there, where he was physically going but also where the camera was going, were at a pretty high level.”
“When I’d be editing sequences of press conferences, I would be like, ‘Wow, this one’s really well done,’” Steve said. “At first, I thought maybe I shot it, but then I realized [Jackson] shot it. And it was like, ‘Well, he sure didn’t need me whispering in his ear, pulling his earbud out.’”
Steve isn’t someone who gives himself much credit for his cinematography, but the impact of his style speaks for itself.
“Steve always puts himself down about his shooting, but he really is one of the great documentary shooters,” Piper said. “And it’s not because he [crafts] the most beautifully composed shots; it’s more just that he’s listening. He’s not falling in love with this shot so much that he’s going to miss things — he’s paying attention to what’s actually happening. He’s listening.”
Steve shared a similar, unprompted observation about Jackson.
“I take great pride in watching my son work and seeing that he really gets it — he’s listening. When people are talking, he’s listening,” Steve said. “You can always tell when a camera person is really listening, versus just getting shots. And he’s really listening because that’s governing what he shoots and what he gets and how he shoots it. That’s not something everybody learns. He’s pretty young and he’s learned that.”
Steve is learning, too. His process is changing, along with how his work is being seen. In an interview with Filmmaker Magazine, he said if he was making “Hoop Dreams” today, it would be a documentary series. Always a proponent of long movies, the episodic model has provided an excellent template for the vérité stories James wants to tell, but the docuseries is a form likely to be defined by that next generation of documentarians. These are the filmmakers that will grow up with them, who will be influenced by them, and who will carry on those lessons into whatever form documentary storytelling takes next.
Right now, we’re seeing the legends of the past and the filmmakers of the future learn from each other. “City So Real” just makes that temporal connection personal.
So what did Steve shoot at Daley’s Restaurant, while Jackson took his mom home from the doctor? People. After Jackson and Piper gobbled up footage of the cajoling campaign advisor, Steve shot interviews with the owner, as well as the caroler.
“While we’re sitting there eating,” Piper said, “this woman came up to our table and she was saying [to Steve], ‘Oh, you’re a silver fox,’ ‘You’re so handsome.’ It ends up being the woman in the film who’s singing. Until she told us on camera, we didn’t even know she was homeless. He was just so taken by her.”
The scene audiences can see in Episode 3 is short — maybe five-and-a-half minutes. Most of it is Phillip working the room for his candidate, Paul Vallas, but there’s also snippets of conversations between a server and her customers, glimpses of the kitchen staff putting out plates, and, yes, a woman singing “The First Noel.”
“The first half is all Jackson — beautifully done,” Steve said. “What I love about that scene is it’s both of us together having filmed important parts of it, but very different parts of it.”
“That was one of our great, tag-team moments,” Jackson said. “The James boys doing their thing.” —Ben Travers