Featured Filmmaker: Gay Dillingham, Director of “Dying to Know: Ram Dass & Timothy Leary”

On Opening Night of the Maui Film Festival, three beautiful venues will fill with moviegoers: the Celestial Cinema at the Wailea Gold & Emerald Golf course, the Seaside Cinema at the Grand Wailea, and the Castle Theater at the Maui Arts & Cultural Center (MACC).

Opening the festival at the MACC we have Dying to Know: Ram Dass & Timothy Leary, a “cosmic buddy film” featuring the two revolutionaries. Bonus points: the film is narrated by Robert Redford.

Gay Dillingham - Dying to Know

Gay Dillingham, Director, “Dying to Know”

We caught up with director Gay Dillingham who is here on Maui to present her film with a Q & A to follow. She reminds us that the screening is a benefit for the Love Serve Remember foundation set up in Ram Dass’ name, and that the world-renowned spiritual teacher himself will be in attendance (likely the only time he’ll attend the screening of this film.


Q: How did your film come to be? 

A: It started on a whim in 1995 while dining with good friends, discussing the news of the day: “Timothy Leary announced he was dying.” My dinner companions were all baby boomers in their mid 40s, I just 30.

I’d seen Leary in the 80s on his college lecture circuit (in his cyber-techie manifestation) promoting LSD, Leary Software Design. I was not all that impressed at the time as I experienced Leary, the showman, not the man. I also remembered my brother who I adored getting in trouble for driving 2 hours to Oklahoma City one school night in 1978 to see a guy named Timothy Leary. I would later realize why he took that risk. In college like many others, I had read and loved Be Here Now, the so-called hippy bible written by Ram Dass formerly known as Richard Alpert, a Harvard Psychologist.

When I was 17 that same brother who had gone off to see Leary died accidentally at the tender age of 20. That loss became a major turning stone in my life and vision.

Back at our 1995 dinner my soon-to-be husband announced, “We should get Ram Dass to come down from San Francisco for a final good bye with Tim.” He would make the call to RD and I would direct – a curious decision given I knew the least about these two men. Within 48 hours I prepped the questions so that Ram Dass could facilitate a lively dialog/interview. I wanted the environment to be as open as possible; the “set & setting” had to support their decades-long relationship for an honest, lively final discussion & perhaps, final good-bye. This meant the crew and equipment once set up had to disappear. I realized this was risky given I was dealing with two known anarchists. Where would it lead? I clearly did not know. The camera’s rolled and as Tim said at the end, “Thanks for bringing us together so we could make love in public.” A cosmic buddy film – a love story was underway.

Following this 1995 relationship story I have discovered death & psychedelics have been some of my greatest teachers in life, and this project pulled these themes together in a remarkably natural way. I was fortunate to get a last solo interview with Tim just before he died. I managed another solo interview with Ram Dass in the very narrow window right after Tim died and before Ram Dass’s stroke in Feb 1997.

I loved the project but my own life became overwhelmed with the death of my father, the launching of an environmental technology business with my husband and 8 years heading up environmental management for the state of NM. In that regard, I’ve now worked 25 years on some of our most intractable environmental problems from nuclear weapons and mass extinction to passing the most comprehensive climate change regulations in the country only to see them overturned. I continue to ask, “Why do we sit by paralyzed with all the information at our fingertips, yet are unable to act?” Perhaps it has something to do with our blind spot, our cultural resistance to that looming mystery in the human landscape – our own mortality?

I touched in with Ram Dass over the years interviewing him, getting to know him, learning from him while trying to figure out how I was going to finish this film that was now haunting me. The more time went on the more I realized the story was mine to tell and was ever more relevant to my own life and, so it seemed, to the American psyche. Like many in my generation I had inherited caricatures of these two men. I needed to reconcile that media abstract with the man I met on his deathbed. In Leary the man I found an intelligent, searching, vulnerable, honest and oh so human being. He was a natural risk taker breaking conventional boundaries for what he believed could bring about expanded consciousness. He was naïve and paid dearly. Over the years Ram Dass’s body become ravaged by his stroke, pain his constant companion yet he seems to live in a state of unconditional love. How is this possible?

The film reaches deep spanning 80 years of footage. As we experience the arcs of their lives and relationship we see the complexity & humanity beyond the caricatures. This part of history I felt was worth a deeper look. I’ve tried to neither glorify nor demonize but see the remarkable human stories composed from lives well lived.

I’ve seen this film deeply touch those that have no idea who these men are to those that knew them well.

Q: What was the most challenging thing about making this film?

A: The most challenging thing about making the film was first trusting my intuition that this was a unique story not yet told and worth telling. Secondly to find the time required and it deserved to make a quality film. The other challenge now is marketing. People may think they know what it is about but are always surprised and delighted.

Q: What type of experience do you hope the film will bring to viewers?

A: My hope is that the film inspires deep meaningful conversations about some of the things that we want to talk about but has remained mostly in the shadows. I’d like the film to help liberate our thinking/feeling in unique ways. For me, this filmmaking journey has led me further down the path to “think for myself” with “unconditional love”, and my hope is that it can do that for you.

Q: What do you think our Maui audiences will appreciate about your film?

A: I think folks on Maui are largely open minded, visionary types so much of this film will resonate quite naturally. Maui folks seem to be more connected to nature and her cycles than most places, hence connected to life & death.

Q: What is your connection to Maui?

A: This film has a very deep connection to Maui in that Ram Dass has chosen it as home. I could not imagine a better place to launch/birth this film than with him in the home and people he loves so much.

Ram Dass & Gay Dillingham

Ram Dass & Gay Dillingham

The Featured Filmmaker series is coordinated and written by the Maui Film Festival’s Filmmaker Liaison and Social Media Director Sara TekulaClick here to see all of the Featured FIlmmaker posts and be sure follow us on Facebook and Twitter to get live updates from the festival.