Anne de Mare and Kirsten Kelly’s “The Homestretch.” Courtesy of Kartemquin Films.

Kasey, Anthony and Roque are three extraordinary Chicago teens with personalities and aspirations that are a natural fit for the big screen. They also just happen to be among the students, numbering over 19,000, currently enrolled in Chicago Public Schools that are homeless, yet none of these young people allow themselves to be defined by that status. “The Homestretch,” one of the year’s best and most vital documentaries, follows the parallel storylines of these budding adults as they strive to defy the odds and make a better life for themselves. The film’s directors are Anne de Mare, an award-winning playwright and founding member of The Independent Theatre Company, and Kirsten Kelly, an award-winning theatre director and co-creator of the CPS Shakespeare program, which invites high school students to create an original Shakespeare production. The program was recently honored at The White House with Kelly and First Lady Michelle Obama in attendance.

Indie Outlook spoke with the filmmaking duo about their longtime collaboration, the cathartic power of theatre and the misleading stereotypes they hope their film will shatter for good.

When did you both first start working together?

Anne de Mare (AM): Kirsten and I had worked together in theatre many years ago and we had a very good working relationship. She’s a really wonderful theatre director and she had directed a play that I wrote in Chicago back in 1999. Artistically and storytelling-wise, our sensibilities were a great match. We got into filmmaking together with the documentary, “Asparagus! Stalking the American Life,” which we made and finished in 2008. As directors, we work very closely in terms of the storytelling—we both [operate] cameras, we both run sound and we both do interviews. Our skills are very complimentary.

Has your background in theatre enhanced your approach to filmmaking, in terms of understanding story?

AM: Yeah, absolutely. It’s given us an understanding of how to tell a story through character.

How extensive was the shooting process?

AM: We spent a tremendous amount of time in what I would call the research and development phase of the film. We worked with about seven young people over the course of the four years that we were filming. We also spent a lot of time at [The Night Ministry’s] emergency overnight youth shelter, The Crib, and Teen Living Programs. It was an organic process that resulted in Kasey, Roque and Anthony rising to the surface as the three stories that we felt, woven together, would tell the most comprehensive story. It was really important to us that we showed different pathways into homelessness for young people and different options for getting out of homelessness.

How were you able to gain the trust of your human subjects?

AM: We were committed to spending a long period of time with these young people to get a deeper story. The relationships that we forged with them can only be built over time.

Kirsten Kelly (KK): We were working with kids who have been through trauma. The majority of adults in their lives have betrayed or abandoned them in some way. When you are another adult coming into their lives, you feel a huge responsibility in allowing everything to be on their terms as much as possible while building the trust in a way that causes them to feel empowered.

You also want to avoid making them feel exploited in any way.

KK: Yeah, that was the hope. We really tried to pay attention to that and be conscientious about that, and we certainly don’t have the necessary level of training or experience with working with kids at that level of trauma. We were looking to have some really important guides along the way. Their counselors who are in the film were also guides to us as well. We wanted each of the kids to have an outside person that would be able to talk them through the process of the film. The kids could talk with their counselor or teacher or another person that was neutral, and I think that was really key to keeping the experience as healthy as possible for everyone.

One of the most memorable characters in the film is Roque’s guardian, the amazing teacher and mother Maria Rivera, who feels compelled to help others in part because of her own backstory.

AM: For many of the people who spoke to us, the biggest element in their success that enabled them to overcome a lot of the obstacles they faced was having a caring adult that served as a stabilizing force in their lives. Maria is a total rock star and she will be the first one to tell you that there are teachers and social workers and so many other people who work to support homeless youth every day. She’s a wonderful character and a wonderful person, too. Once you get into the landscape of youth homelessness and start to work with teachers and social workers and service providers, you begin to understand how many extraordinary people are working in this field and how much it takes to help a young person succeed.

The Rivera Family in Anne De Mare and Kirsten Kelly’s “The Homestretch.” Courtesy of Kartemquin Films.

What sort of catharsis can theatre bring to kids like Roque?

KK: I think there’s something really powerful about discovering how words have power. It’s not just about what you say but how you say it. These ancient stories may have no relevance in your life, but once you infuse them with your own personal experiences and point of view, they become really powerful. When Roque came into that program, he would not speak. He felt completely invisible, and I think that “awakening of voice”—and what that means on various levels, consciously or unconsciously—has the potential to happen in the CPS Shakespeare program. You are being asked to speak these powerful words and also bring yourself front and center. The audience wants to hear your point of view and your experience and your humanity.

It was this very weird symbiotic moment when we started understanding that Roque’s story so deeply connected to Hamlet’s story, considering everything that went on with his uncle and his parents. It was really amazing and bizarre in how deeply that connected. We’ve done so many different plays in that program, but there’s something about Hamlet and the betrayal at the center of it that resonates with kids. They get that sense of betrayal more than the professional actors I’ve worked with. They’ve experienced that level of betrayal, and they can bring that forth in the storytelling.

How close was your collaboration with editor Leslie Simmer?

AM: We edited the film on and off for about a year. Leslie, Kirsten and I had an amazing experience attending the Sundance Institute’s Documentary Edit and Story Labs in Utah, where we spent time working closely with amazing advisors and looking at the story from a different standpoint. That was really valuable. Documentaries are made in the editing room every bit as much as they’re made on location. Leslie had a real emotional connection to the material and a profound understanding of what story we were working to tell.

KK: I think the three of us all brought different strengths to the process of storytelling. It was great to have that inherent trust that we were all moving towards the same film and just looking at different ways of how to get there. The challenge of the film was how to weave these three stories together in a way that adds up to something greater. Kasey had to inform the next scene with Anthony, who had to inform the next scene with Roque, so that the whole emotional arc remained consistent throughout. That was what we were constantly coming back to as a threesome.

AM: You have to tell a story in the way that it opens up to you. With certain storylines, we understood what they were and the arc of them earlier than others. Things would shift and change. We’d think that we would be done with a particular storyline and then decide that we’d have to go shoot additional footage. The community at Kartemquin was great in terms of their feedback. But in terms of the process, it would take as long as it takes and that became an interesting lesson in patience.

KK: I think that’s the value of independent documentary films. You never have the funding to do all of it from the get-go, and you’re constantly trying to find the story in a scrappy kind of way. There is some freedom in that you don’t have an executive board saying, “This has to be in by this time.” All of your choices can be dependent on finding the story.

Kasey in Anne De Mare and Kirsten Kelly’s “The Homestretch.” Courtesy of Kartemquin Films.

Would you consider doing follow-up interviews with these subjects?

AM: It might be interesting to come back another time, maybe in three or four years, and see where they all are.

KK: It’s the question that everybody in every talk-back wants to know: what’s the update on the kids? When we tell an audience that Roque is in his second year of college, they applaud. But Roque can still only go part-time and only has two years on his work permit. He’s trying to work as much as he can so he can still go to school in case his work permit isn’t renewed. It’s important for us to make people aware that while Roque is still in college, it’s going to take him eight years to complete it. These obstacles don’t just magically go away. Yes, Anthony has the potential for a really good job, but he does have to go through a lot more training and he has to do a lot of work to be able to realize his dream of having a son. He also has a lot of work to do in terms of parenting skills. We want the audience to understand that, in all of these cases, the answer is not a simple one.

AM: The strongest solutions for this crisis come from the communities themselves. They come from inside the community and we encourage people, in every community, to find out who is working with homeless youth and who the homeless liaison is in the public schools. Find out what they need and support them. Get involved from a very grassroots level with the situation in your own backyard.

KK: One of the things that we kept hearing over and over during our meetings with service providers and liaisons was that the number one reason why there was not support for these kids and these programs was this kind of pervasive negative stereotype of the troubled, drug addicted kid. That was the only image that was out there in society, and it’s what usually comes to mind when someone says the phrase, “homeless youth.” With this film, we really wanted to break that stereotype and bring awareness to the fact that the majority of kids going through this struggle have much different stories to tell.

“The Homestretch” opens at the Gene Siskel Film Center on Friday, November 21st and screens through Wednesday, November 26th. For tickets and showtimes, click here. Visit the official Homestretch website for more information on the film’s impact campaign. The film is a co-production between Spargel Productions and Kartemquin Films.