This Toronto filmmaker wants you to know homelessness isn't some far-off possibility

Early in the pandemic, Jason Cipparrone spotted a sight he'd never before seen in his neighbourhood.

"One day I walk out of my apartment and I walk two blocks down by a church that's in the community, and I notice that there were about 400 people lined up on the sidewalk. It spanned multiple blocks, people waiting for the food bank," he told CBC's Our Toronto.

"That was something that I've never experienced before living in Toronto."

Out of that moment, Generation Homeless, was born. Seeing the stark impact of the pandemic on individuals, Cipparrone decided to document the experiences of those struggling with homelessness in Canadian cities. 

Now the Toronto-based photographer and director has partnered with the CBC Creator Network for a series taking an in-depth look at those affected by Canada's housing crisis. 

Cipparrone's first episode features a Toronto woman named Amy Finn, 22, who is living on the streets as she waits for housing, while her three-year-old son lives with his grandmother.

Finn lives in different parts of the city, sometimes on the streets and sometimes in parking garages — anywhere she can find that she feels is safe to get some sleep, Cipparrone said. 

"I met Amy last year because I was doing some portraits in the community," he said.

A 'holding pattern' of homelessness

"And it just became obvious to me right away that she had such a light and shine about her that I needed to do something that focused on these type of people — people like Amy, who are young, who have so much in front of them, and yet who are kind of right now in this holding pattern," he said.

For Cipparrone, gaining trust with individuals to tell their stories is crucial and often takes time. 

"You don't gain trust or access one day and then have it indefinitely," he said.

"I think a lot of people approach these topics like that. There is a sense within the academic community that you want to study things. Well, unfortunately, you [can] end up turning people into numbers too, and there's often a lack of compassion when it comes to it."

What I've realized through this process is that if you don't own something, your voice is very small when it comes to trying to get people in the political realm to even speak to you ...- Jason Cipparrone

"For me, this has been probably a year and three months of working on that trust and access. It is still an ongoing thing," he said. 

Cipparrone says working on this series, and telling stories about people experiencing homelessness, has been eye-opening and has helped him better understand the marginalized population.

He says his preconceived notions about people experiencing homelessness being people who haven't tried hard enough or worked as hard as others has shifted through this series.

"We have a number of gaps within our municipal, provincial and federal system with regards to housing and the upswing of people living on the streets and essentially being in a position where eviction might actually occur for them," he said.

"What I've realized through this process is that if you don't own something, your voice is very small when it comes to trying to get people in the political realm to even speak to you or to engage with you about the issues that you see.

"And COVID basically caused a massive exacerbation of people out on the streets. It confirmed to me something that I think we all know, which is that we have systems in place that are not functioning in a way that reflects the true nature of Canadians."

Cipparrone hopes his series gives viewers an opportunity to see the personal side of those experiencing homelessness and the barriers they face. 

"I hope that anybody who watches this is compelled to deeply understand Amy as a person, her issues, but then also ask the greater question of why are those things so tough for her to accomplish? Why can't she get ID, you know, until people want to really have that discussion and dive into it?" he said.

"That means discussing things that might end in tears. It means discussing things that might end in an argument. But the point is that the longer that people avoid that discussion, the worse that it gets for everybody else."

You can find this and other stories about the city on Our Toronto — Saturdays and Sundays at 12 p.m., and Mondays at 11 a.m.