“Figure out what you’re good at, be honest with yourself about whether or not you have good taste.”-Kyle Leland

Photo by: Felix Penzarella
Photo by: Felix Penzarella

Exclusive interview with Kyle Leland – Producer, 1st AD, & Editor

With the privilege of growing up in the inner city of Chicago, Kyle was able to study at Second City and iO Theater from a young age. His first film was a documentary about shrooms. The priest in charge of the film program at his Catholic high school in downtown Chicago was not amused. His first film project in college was an adventure story about masterbation. His conservative Republican professor was slightly amused; it got a B-. Studying documentary at Columbia College created opportunities to shoot promotional videos for theatre companies all over the city, and eventually, TV spots for major sports teams, Budweiser, Subaru, and many other evil corporations. During this same period of 10 years or so, Kyle worked as a Production Assistant herding and placing extras in films and TV shows such as Divergent, Contagion, Shameless, Chicago Fire, and many more. While those experiences paid the bills and sharpened certain skills, they weren’t what he really wanted to do; tell his own weird stories. In the last 3 years, Kyle has pivoted towards his own projects and produced 3 short films and now a web series, resulting in screenings at over 20 festivals including Cannes Film Festival 2018.

NY Glam: Tell us a little about yourself, growing up and your passions.

I was born and raised in Chicago near Wrigley Field, yet was a lifelong Sox fan. I was the only ginger with mostly older siblings in an Irish-Catholic family of 7. These are just a couple possible causes of where my anti-conformist obsessions may have come from. With some family in the industry, and the only virtual interest as a child being making trips to Blockbuster to load up on new releases, I became set on filmmaking very early. I was shooting short animation with my dad’s camcorder and enrolling in film summer camps before 5th grade. I was a class clown making frequent trips to the principals office, one of the consequences of an ability to gain an audience. As a natural storyteller, my first fully realized short films were psychedelic, experimental documentaries about high school drug use featuring soundtrack from Velvet Underground and The Beatles. They ruffled the feathers of the priests in charge of the film program at my Catholic high school. Instead of homework, I religiously rewatched Kubrick, PT Anderson, and Wes Anderson, like many filmmakers from my generation. That, messing around on piano, smoking weed, and reenacting Jackass scenes in the streets of Chicago with friends and my camcorder were pretty much my only activities as a child.

NY Glam: Did you have any specific influences growing up that lead you towards the film industry?

I was fascinated with the successful careers some family members had in the industry – my aunt was a Broadway voice coach, uncle a Hollywood teamster, and other uncle an award winning location manager. But when I came across the films Rushmore, Magnolia, A Clockwork Orange, and 2001: A Space Odyssey in junior high, I knew I had to be on the creative end.

NY Glam: What are you currently working on?

I’m currently pushing two short films through festivals with this same team as a Producer/Editor/AD. Also getting ready to submit a web series that I wrote and directed called Hammersmith through web festivals now. Hoping to shoot a micro budget pilot called Mid-to-Late this year. And plan to write out a few outlines for some feature concepts as soon as I have free time. All this while working freelance on Chicago commercials as a director/editor.

NY Glam: What were your main responsibilities on this film?

I was first a friend of Abby’s for her to bounce ideas off of, then I fell into the 1st AD position because of my Production experience. I then consequently fell into the editor position. And at that point, it only felt natural that I stick with the project through the rest of its run as a Producer.

NY Glam: Can you tell us about your experience in working with the director and actors in this film?

Well, Abby Pierce was an old friend, and told me about a concept she wrote with a friend that she wanted to direct. It was fascinating talking through every possibility for the project. Then when shooting arrived she introduced me to an amazing group of theatre actors and a crazy talented camera crew she found through friends of friends. When we were on set it was like a house party. Everyone was chill and motivated, and constantly enthusiastic about the way everything was turning out on frame. It was smooth and fun. And to top it off, I got to work with Charley Koontz and Graham Beckel which was intimidating and awesome.

NY Glam: What was the most important thing for this movie to achieve from a narrative and character standpoint?

The most important challenge on my mind was to clearly and entertainingly build the world of Magical Realism through the literal heart exchange metaphor. With our limited time with the camera and crew, we only had a couple shots to establish that this insane, weird act of ripping out and giving one’s heart to their lover was a common and normal thing to do in this film’s setting. Without this concept becoming immediately accepted, the audience would be too distracted to take on the characters’ relationships and the story exposition. Luckily the writing, cinematography, performances, and a couple quick editing fixes were planned out well enough that everything clicked in a charming and simple way.

NY Glam: What other films have you produced?

I produced another short film with director Abby Pierce called Go Ahead, Grab Time By The Throat which recently wrapped up. I wrote/directed a short film for a timed-film-competition called Hammersmith that ended up winning and screened at Cannes 2018. I have since turned that short into a web series by the same name and shot 5 more episodes, soon to be released. Before that I made about 20 amateur short films and another 20 local commercials/music videos.

NY Glam: What makes a film interesting for you? What are three qualities that you look for in a movie?

Honesty, controversy, and awareness are all I really care about in any art. The more pathetically and embarrassingly honest a film is, the deeper someone can identify with it on a level that they normally can’t communicate to their closest loved ones in their day to day life because of internal shame. And that’s the point of art – a more soulful communication. Controversy is important because if it isn’t controversial, then it probably isn’t saying anything new. Controversy is usually a sign that a film is tapping into something that people usually don’t dare to talk about, but if it exists, then it’s worth examination. And  lastly, awareness is embodied as harnessing true craft in creating a point of view for a story. Awareness of every characters’ motivation, including the antagonist’s. Awareness of who will see this, in what context, and how the audience could interpret it. Awareness of what the film is – genre, scope, message.

NY Glam: What project helped you launch your career?

A promotional documentary I made for an experimental theatre house that screened with their performance at Chicago’s Museum of Contemporary Art in my early 20’s was the first big project on my reel that lead to other gigs. But my short film Hammersmith winning some festivals and screening at Cannes definitely gave the biggest jumpstart to my career.

NY Glam: What criteria do you use to select a script, screenwriter, director, etc.?

Pretty simple: they have to seem like a chill, cool person who isn’t an asshole… unless the script is realllllly good. A script that stands out is one that seems like it would play well with audiences in today’s world. One that seems authentic, says something that doesn’t seem like has been said before, and genuinely surprises me, or makes me laugh or cry when reading… but that’s like.. very rare/non-existent.

NY Glam: What are you most proud of? Describe your biggest accomplishment to date?

Probably same as 2 questions above; having my documentary screen at the MCA, writing/directing a short comedy that brought me to the Cannes Film Festival, but also, this film Eat Your Heart Out won an award at its first festival which resulted with the prize of screening before a special rooftop premiere of Marc Maron’s recent film Sword of Trust.

NY Glam: Do you have any upcoming projects that you’re super excited about?

Hammersmith the web series that I wrote/directed/produced is currently my entire existence. It’s post-production and promotion is consuming me right now, but I think people are going to love it and laugh their asses off, so I’m very excited about its upcoming release this summer. You can follow its release at HammersmithSeries.com

NY Glam: What advice would you give to someone who is aspiring to enter the film industry, especially as a producer?

I’d say get over your narcissism and greed. Become an engineer or a nurse. The world is ending. There’s enough of us assholes seeking fame and fortune as is. But, if they’re hoping to change a world mindset through film, then I would say: figure out what you’re good at, be honest with yourself about whether or not you have good taste. After that, find people who are good at the things you aren’t and have better taste. Work with them, let them help you, and help them with what you’re good at. Also find someone who is mean/brutally honest and will give you insightful criticism that’ll help you build. Also, go to every single film event going on around you and join every group available to you. Talk to everyone and follow through with further communication.

NY Glam: Can you discuss any future projects or direction you are taking in regard to film making?

Again, my web series coming out this summer Hammersmith is the only upcoming release on which I’m focusing, but I’m planning on making a deeper dive in tone/genre for future projects.  I plan to lean away from lighter comedy which I have been doing a lot of recently, and instead, working on my skills of developing suspense and creating darker atmospheres. I think that’s where my craft will bring out a more original artistic voice.


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