Director of Silk Road Tiller Russell Is Fascinated By The Good, Bad, And Everything In Between

The acclaimed writer/director of “Night Stalker” discusses weed, filmmaking, his new movie “Silk Road,” and the blending of documentaries and movies whenever possible.
Director of Silk Road Tiller Russell Is Fascinated By The Good, Bad, And Everything In Between
Courtesy of Lionsgate

Tiller Russell’s path to filmmaking is a story of listening to yourself, risk taking, and the bountiful gift of happenstance. When we connect by phone, Tiller is eager to talk more about his filmmaking journey from newspaper to big screen, his new feature film, Silk Road, and his life-goal checkbox of speaking with High Times Magazine. “If only my sixteen year old stoner self could see me now. He would be so thrilled.” Our conversation takes a deeper dive into Tiller Russell’s mind and attempts to understand how he’s able to communicate emotionally conflicting subject matter through his work while maintaining an objective lens.

First off, is your relationship with cannabis the same now as it was when you were a teen?

Tiller Russell: I literally had boxes and boxes of High Times Magazines, so as a lifelong fan and stoner-geek, it’s a trip and an honor to all these years later speak with the magazine. I’m happy it’s all come full circle.

Once upon a time, I was a deep stoner. In the great irony of life, I waited for weed to become legal only to then decide it was time to get sober and be straight. I waited my entire life for the High Times interview only to not be stoned. And not for any particular reason other than I’m enjoying the clarity of being where I am right now, making the work I’m trying to make and doing the best that I can. I’m just really enjoying being fully present in the ups and downs, while still having the peak experiences, but doing so straight. It’s a whole new, weird and fascinating chapter, and for whatever reason, here I am.

I went through a very intense process where I was making three projects simultaneously: Night Stalker for Netflix, The Last Narc for Amazon, and Silk Road for Lionsgate. It was literally so much pressure and was so intense that I decided if I was going to go through it and do those projects justice—by pouring my heart out and leaving my best out there—then I was going to try doing it without anything other than my consciousness. I made that decision and I’m enjoying it, though I never thought I would. It doesn’t mean that I won’t smoke a joint tonight, or tomorrow or in ten years, it’s just where I am at the moment and I’m doing my best to ride the wave.

So when you were enjoying High Times Magazine as a teen, were you also thinking about making films?

Tiller Russell: I grew up in Dallas, Texas and was always a movie nut as a kid, but I didn’t know anybody in Hollywood, didn’t have any connections and thought it would be a miracle to actually make a movie.

My path ended up through writing and through being a reporter, specifically on crime-related stories. My dad worked in the DA’s office, so having grown up around cops, courts and precincts, that world always felt natural and comfortable to me. The people in that environment also seemed extremely compelling, regardless which side of the law they were on. Whether it was the crooks and gangsters or the cops who were pursuing them, or sometimes the thin and porous line between the two, the world of crime was a lifelong fascination for me.

Years later, I crossed paths with director Errol Morris when I was reviewing one of his movies for the paper. It was the last interview of the day and I think he was sick of answering the same questions and he was like, “Listen, man. Do you want to just grab a steak and a bottle of wine?” We ended up going to the top of this hotel and had a lovely, drunken evening together. At the end, he put his hand on my shoulder and said, “You’re either going to spend your life writing about people like me, or you’re going to try your hand at this.” It literally prompted me the next day to quit my job at the paper and embark on the path to becoming a filmmaker.

Did Errol then become a mentor figure of sorts for you?

Tiller Russell: It was more of a momentary crossing, and I bet if you asked him about it, he might not even recall it. For him, it was just another night on the tour, but for me it changed the course of my life. I’ve always felt like I owed him an incredible debt of gratitude and would one day love to close the circle and reconnect with him and thank him.

Interestingly enough, the DA’s office depicted in his film, The Thin Blue Line, was the DA’s office my dad worked in when I was a kid, so there was already this weird, harmonic connection, and because of him, I’ve gone on the wild ride of making movies.

And it sounds like since you were organically predisposed to the world of crime and law enforcement, that became your focus.

Tiller Russell: I think I imprinted on it because it was a milieu and it was a set of characters that seemed familiar to me, so it was a natural continuation of that exploration. When you’re a kid being dragged around to those places, you’re a silent bystander, peeking through the back. But suddenly with a press pass and later with a camera, it was like, “What it is it like to be a gangster when that’s your job?” I was so fascinated to ask somebody, because for those guys in that life, it is a job and it is a profession. It’s a career. So the same levels of processing, methodology and craft—although it feels odd to say—all apply.

Similarly, on the cop side of the equation, the same thing is true: fascinating, larger than life, against the grain characters. On both sides, everytime you walk out the door and have a gun at your hip or in a holster, you’re taking your life in your hands. There is an inherent, intense drama to those walks of life.

From a filmmaking standpoint, how helpful is your background of understanding law enforcement and those who engage in more illicit activities?

Tiller Russell: Culturally, we all have this fascination with crime. If you look at the history of America, in some sense, it’s the history of the outlaw. From Billy The Kid, through The Godfather, these are stories that we are gripped by. What is it about the human psyche that makes those stories so fascinating? I guess I’ve always tried to satisfy my own curiosity and passion, and in doing so, hopefully entertain people and take them on a voyage.

Exclusive Clip From Silk Road:

Exclusive clip; courtesy of Lionsgate

For your two most recent projects—the docuseries, Night Stalker and the feature film, Silk Road—how do these two different forms of storytelling satisfy your creative curiosity?

Tiller Russell: As mentioned before, I was making both of those projects simultaneously, and there was this toggling between narrative storytelling and nonfiction, documentary storytelling. I’m somebody who walks in both worlds, having spent time writing for the paper and in writers rooms for network television, and also a lot of time in edit bays making documentaries over the years. I’ve acquired knowledge of both the fiction side and the nonfiction side, and what I try to do, wherever possible, is blend those two worlds.

Even though Night Stalker is a documentary series, I’m trying to find cinematic tools that make it feel as if it’s a movie and that it has a propulsive narrative drive to it. When making Silk Road, I wanted to have the authenticity and the lived-in kind of nature of a documentary. Even though Silk Road contains actors portraying characters in a narrative film, you want it to feel as grounded and real as possible.

You have a title card at the beginning of Silk Road that says, “Based on a true story, except for the parts we made up.” How do you balance the “truth” with telling a compelling narrative?

Tiller Russell: Every feature film is a fictional film, even when you see the words “based on a true story.” When you actually get into it, you have actors portraying real life, and almost across the board there end up being stories that are compressed, characters that are composited, or facts that are used as a launchpad to tell an emotional truth. It felt important to me to acknowledge at the outset that this film is based on a true story, and many of the events, words, characters, people, and  lives that you’ll see are drawn from the real world.

At the same time, there are elements of the movie that are fictionalized because it’s not a documentary and cameras were not rolling the entire time. I’m trying to adhere to the emotional, psychological, and spiritual truths of the story more than the “facts” of it and it was imperative for the audience to know this, but also set the tone of the movie.

Ross Ulbricht—the creator of Silk Road—had this “bomb the system” ethos to his way of being in the world, similar to the origins of High Times Magazine in how High Times was a product of the counterculture intending to circumvent mainstream media and give people what they wanted in a fundamental way.

Did you have conversations with Ross directly to help inform how he was portrayed on screen?

Tiller Russell: There was a brilliant Rolling Stone article written by journalist David Kushner. He had gotten access to Ross’ family, Ross’ ex-girlfriend and created a very relatable portrait of him. At the time, Ross was locked up in New York awaiting trial, and I sent him a letter very early on knowing that his lawyers—rightly—would never let me get access to him until he had been through the justice system and exhausted his appeals, so I never heard back from him at the time.

What ended up happening was, his ex-girlfriend—Julia V, who is portrayed in the film by the actress Alexandra Shipp—ended up becoming a consultant on the film. As I was writing the script and as we were going into production, she would offer me insight into her perspective as to who Ross is or was and what was in his heart and soul.

There was also a very rich historical archive. There were all of the posts that Ross had made as ‘Dread Pirate Roberts’ on the Silk Road website. There were the chat logs, both the encrypted and otherwise which were made publicly available, and then there were the diary entries. Ross, having had an instinct early on that he was in some sense a visionary and that he would in some way make his mark on the world, kept diary entries along the way. When he was arrested and when his laptop was confiscated, those diary entries were entered into the evidentiary and public record. All of the voice over used in the film that you hear Nick Robinson—who plays Ross Ulbricht—speaking, all of that is drawn from Ross’ journals, from the chat logs and from his public posts as ‘DPR,’ with the intent of getting as close as possible to who he was.

As recently as the end of the last presidential administration, Ross and his family were hoping for a presidential pardon, which obviously did not come through. That morning, I woke up and looked on the Bureau of Prison’s website to find Ross’ name and the particulars of where he was incarcerated. It listed his name, Tucson Penitentiary and Release Date: Life. It was bracing for me to read those words, so I sat down and wrote Ross another letter which said I’ve made a film that’s from the contrasting and conflicting narratives that I’ve drawn from to triangulate my portrait of you, and now if you ever want to sit down in person, let me know and I’ll be there because I would still very much like to do that.

That’s Fascinating.

Tiller Russell: People are fascinating. Good people are fascinating and bad people are fascinating, and people with a lot of the gray area between the two are the most fascinating of all. When you’re willing to connect and be present and hear what people have to say, it’s almost always riveting.

Audiences are smart and will draw their own conclusions, and it’s not my job as a filmmaker to make these conclusions one way or another. I want to tell the stories, draw the portraits, and then it’s up to viewers and audiences to make up their own minds where they land in terms of assessing these people and what they did and what their lives have meant.

Do you think that if Silk Road was created today, Ross would have ended up in the same predicament?

Tiller Russell: In the seventies, eighties, nineties, or early two-thousands, the notion that you could walk into a weed store and get any strain imaginable was preposterous. Never in a million years as a kid would I have imagined that such a total cultural shift would have happened.

At the time, Silk Road was such a threat to law enforcement because it changed the drug game over night and it changed the war on drugs. In complexity science, there’s this idea of cascading conflict, where so many things are happening in so many different ways that it becomes like an avalanche all at once. I imagine that’s how it must have been experienced from the law enforcement perspective, when suddenly the mailman is your dope dealer and he doesn’t even know it. That’s so challenging to the status quo. 

The thing about Silk Road [the movie] is that it is a period piece, even though that sounds funny to say. In the six to eight years since the story has elapsed, the world has changed so radically through legalization, the therapeutic use of psychedelics, and other massive cultural shifts. Certainly, you have to think context is determinative of content in what happened at the time. Ross doing what he did would hardly even be revolutionary today.

Ross is a complicated character and I have conflicting emotions about him as a human being. But this is an important fact: he was sentenced to two life sentences, plus forty years, without the possibility of parole. That’s significantly harsher than the sentence received by El Chapo.

Whatever your politics are, that’s a stunning fact. And while I’m deeply empathetic to someone who lost a loved one who’d bought drugs off Silk Road, and while I can imagine that horror and tragedy and am pained by it, I also feel that the sentence Ross received is pretty shocking.

It will be interesting to see if in ten years, we look back on Ross’ sentencing as something akin to an inflated possession charge.

Tiller Russell: Think about the guys who were busted for a dime bag in the seventies and are doing years in a penitentiary, and how it now seems so profoundly unfair and kind of insane. It does make you wonder with how fast things are changing, how history will look back at that moment, that sentence and what happened to Ross as a human being.

I’m a big believer in second chances. I have failed and made mistakes numerous times throughout my life and have been repeatedly graced with opportunities to try again and do better. I’m not sure of the circumstances or how it would ever happen, but I do hope and pray for Ross at the end of the day that he gets a second chance to make another contribution [to society] because I do think he is somebody who has something to give. I hope that the possibility of transformation is extended to him in the second half of his life.

Follow @lionsgate and check out the film Silk Road, now available everywhere movies are rented

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