After Leary was diagnosed with terminal prostate cancer in 1995, Dillingham decided to sit the two friends (and occasional enemies) down for a final conversation of their years together, death and dying, and the nuances of the mind. The outcome is a riotously funny and heartbreakingly poignant film, with the men's admiration for one another at the forefront.
We chatted with Dillingham about the making of the film and her navigation of these two incredible souls.
How did the idea for the film come about?
I knew both of these men before the project but more as caricatures handed down by my media culture. I had read Be Here Now in college in the 80s and seen Leary when he was on the college lecture tour. I was not that impressed with him then as I only saw Leary the showman, not the man. This 20 year journey was a process of discovering a human story, an untold history of the times and these two characters. But I never set out to make a historical film, even though it is also that. I made a contemporary film constructing the historical piece to make sense of who were these two characters that are having such a lively inspired diverse conversation about our taboo topics of death and drugs.
I was, and continue to be, interested in what they have to say about the process of death and rebirth as a psychologically transformative process. Ram Dass was the first person Tim called when he found out he was dying. Tim states, “Since we have been through so many death rebirth experiences together I thought Ram Dass would understand what this death would be like for me.”
It seems like for much of the film, your role was essentially to direct a conversation between two anarchists. How did that go?
Absolutely anarchists, and it was NOT easy given the conversation had a life of its own, with interruptions and all. As a director I crafting the questions and topics and gave them to Ram Dass to ask. I also decided to focus on set and setting, creating the right atmosphere conducive for them to have this final conversation and goodbye. When I first went to review the material I locked myself in an editing room alone and thought as I pulled my hair out, what have I done? This is all over the place — all interruptions much of it very personal with no context. I stayed in that edit room until I found the matrix of the conversation that held my attention and I wanted to follow.
Is there a specific role you see 60's counterculture playing in our lives today?
I think we are still unpacking much of what happened in the 60s. The revolution/evolution of consciousness did not go away but some of it had to go more underground and is re-emerging now with more maturity. I think it is an important story to look at the lessons learned: good and bad, and understand how we as a society can get derailed, divided and distracted.
To what extent do you think a documentary can tell the truth?
I think a documentary can tell the truth as the filmmaker sees it and to the degree it resonates with the viewer. Film in general can be a shamanic transformative form for healing as well as it can be harmful. It can be like psychedelics, so as Leary and Alpert promoted we need to pay attention to “set and setting."
What was the greatest difficulty you had making the film?
The hardest thing was carrying the film and story 20 years, trusting my instinct, and finding the time to finish it. I’m most proud of “carrying the film and story 20 years, trusting my instinct, and making the time to finish it because it held my attention and love that long. I’m also proud that this film is deeply impacting people, and many are coming back to see this film two, three, four times.
I was told that seeing this film would change my attitude toward my own mortality, perhaps by bringing about more acceptance. Has studying Leary and Dass brought you to see death as a celebration of life lived?
I think both these men have contributed greatly and differently to my perspective on my mortality. I think and feel a real simpatico with their views, which is largely why I was haunted to finish this story, so I could share with others both for very personal and political (collective) reasons.
Dying to Know is playing at Laemmele's Royal Theater in West LA through Thursday, June 30th.