Toronto filmmaker Alan Zweig (Vinyl, I, Curmudgeon) knew author Ray Robertson (What Happened Later, Gently Down the Stream) well enough to nod a greeting on the street, but it wasn’t until a chance meeting at a favourite west-end used record store that the two started discussing their creative projects with each other.

On Saturday, Zweig’s new documentary, 15 Reasons to Live, premieres at the Hot Docs film festival in Toronto. Inspired by Robertson’s personal essay collection, Why Not? Fifteen Reasons to Live, Zweig constructed his film using short vignettes about people who embody the book’s spirit.

Q&Q spoke to Zweig about his documentary and relationship to Robertson’s book.

What made you think this book would make a good film? When Ray told me the book was called Fifteen Reasons to Live (he didn’t mention in that first conversation that the book is actually called Why Not?), there were many things about those words that hit me hard. I have a relationship with lists in that I don’t make them. Most of my life I have said, “Are there reasons to live? What choice do I have? I also felt there was a strong connection between the book and other films of mine, in particular I, Curmudgeon, which is about negativity and trying to move on. I decided I was going to do it before I even read the book.

What did you think after you read the book? The book is not like your normal self-help book “ it’s for people who don’t like self-help books because it’s told from such an eccentrically personal point of view. I don’t know if Ray would describe his book this way, but I have described my film as Oprah for cynics.

I hoped there would be lots of things I could use for the film. But Ray’s reasons are more like essays and less like stories, which would have made it easier. In the end I decided the film couldn’t be my 15 reasons to live “ it would have to come from the book. I was going to take it as a sacred text.

How would you describe the relationship between the book and the film? When I couldn’t find a story I would go back to the book as a reminder of how it inspired me, to see what Ray meant and see how I could apply that to a story. He gave me a map, and I’m going to all those places, but I might not take the same route he did.

What was the most challenging subject? Intoxication. I didn’t want it to be about mushrooms or Carlos Castaneda, I wanted it to be about alcohol. It wasn’t simply because I don’t get drunk myself much. What is a good story about getting drunk?

Individuality and Critical Mind were also challenging. While I agree individuality is a nice feature to go through life with, it’s also somewhat self-congratulatory. Ray can get away with it in the book because it’s extremely personal. I had to find stories that would come in the back door.

Has Ray seen the film? He will see it Saturday for the first time. Sometimes I would see him in the neighbourhood and tell him about the stories. Sometimes Ray seemed excited, other times he said that wasn’t what he meant. But I think he’ll like it. He’s been very encouraging.

I’m not happy that all his novels haven’t been made into films, but I think it’s a cool thing that the book you might have thought least likely to be made into a film will be the first.

This interview has been edited and condensed.