Alright – so today we’ve got the honor of introducing you to Leland Montgomery. We think you’ll enjoy our conversation, we’ve shared it below.

Leland, looking forward to hearing all of your stories today. We’d love to hear about a project that you’ve worked on that’s meant a lot to you.

The most meaningful project I’ve worked on is a recent short that I made called Hotter Up Close. We just finished our festival run with a final screening at Outfest Fusion. There are many different reasons why this particular piece of work is so important to me.

When I was very young, there wasn’t a ton of queer representation in media. There was Will & Grace and Queer as Folk and an occasional storyline on Sex and the City, but it didn’t feel like there were a lot of places where I could see myself represented.

As a young adult, however, that changed rapidly. And queer representation seemed to explode! Which is both great for the culture and a bit challenging for a young artist whose “thing” was being a gay filmmaker.

We conceived Hotter Up Close towards the end of the Trump presidency, and because movies — even short ones — take a million years to make, it wasn’t until the summer of 2021 that we started shooting. By that point, the rhetoric around LGBTQIA+ issues (especially trans issues) began to intensify. The community was under even more pressure as we released the movie and did our festival run. Shootings at drag shows and the dog whistle of “groomer” started cropping up all over the place, and suddenly queer stories seemed as vital and essential as they did when I was young and searching for myself in movies.

Since we released the movie, it actually seems more relevant. Now more than ever, it is a time to celebrate and uplift the LGBTQIA community, and it’s so meaningful that I get to do that with this movie at this moment.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers

Today we’d like to introduce you to Leland Montgomery.

So, before we jump into specific questions, why don’t you give us some details about you and your story.
I originally moved to Los Angeles to be an actor. I’d gone to drama school in San Diego and when I graduated, LA felt like the natural next step. My mom, however, begged me not go go. She’d grown up in Palos Verdes and had hated it. She fled Southern California as soon as she finished college.

When I first got to LA I’d just recovered from pretty horrific jaw surgery and spent the first year of my post-college life with my teeth wired shut. Which meant… no acting, no auditions, and no real job.

And it was during this time that I began to reassess what I wanted to do with my life. My friends – many of whom I thought were tremendous actors – seemed to be struggling, and even once my jaw was unwired and I began to audition, I had this funny sensation in the back of my mind that acting wasn’t something I was fully interested in.

I started to make these little narrative videos with my friends, which soon turned from a hobby into something I was getting a lot of attention for. The first “real” piece of work I directed was a web series called God Particles.

It did pretty well – playing at LACMA’s Young Director’s Night, winning a few awards from the International Academy of Web Television and racking up a bunch of views.

It dawned on me that it might be a good idea to go back to school to study film. I’d worked mostly on instinct, but I knew there was a benefit to going back and getting formal training.Knowing that I didn’t want to leave Los Angeles, I applied to USC and AFI and eventually chose to attend USC to get an MFA in filmmaking.

Have you ever had to pivot?

One story that pops into mind in terms of major life and career pivots centers around a horrible audition I had back in 2012. It was one of the reasons I decided to shift from being an actor to fully focusing on being a director. At that time, I was going out for a lot of “nerd” roles. My reps reached out and were like, “Hey, you’re going to audition for this Super Bowl commercial.” The character description was something like “disgusting ugly geek who no one would ever be attracted to,” and my agents were like, “you’d be great for this.”

So I went, and the whole premise of the commercial was that a homely guy makes out with a supermodel. In the first round of auditions, they had us make out with our hands, like teenagers practicing kissing.

I guess they liked what they saw because I was advanced to the second round, where they had me make out with a blowup doll — which they also seemed impressed by because I moved to the final round where, in front of an assemblage of maybe 25 people, they had me make out with a poor casting associate.

All through this process, my reps at the time kept letting me know how excited they were that I was going to play “disgusting ugly geek” and what a win it would be for my career. When the decision finally came down, they went in another direction. But they let me know I was the first alternate.It was such a humiliating and truly dehumanizing experience that it made me realize, “I don’t think I’m cut out for this.”

Instead of quitting, however, I realized that I should move my focus away from performing and instead into filmmaking, which was a huge adjustment, but one that I’m really grateful I made.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

I think one of the biggest things that’s helpful to know about the creative journey is how important change is. When I first moved to Los Angeles, I was sure I wanted to be an actor. I was so aggressive about finding representation and getting auditions. But as I progressed along that path, I realized that it wasn’t what was making me happy. So I pivoted. I shifted goals, and even though it was scary and a little sad, it was right for me to do.

Longevity is another thing that folks don’t talk about enough. It takes a long time to build a creative career — and sometimes, just sticking it out is a win. Many folks, especially when they’re young, think doing a few gigs just to get by is the right move. And for some, it is. But I spent most of my twenties as a starving artist and nearly burned out. I’ve learned that figuring out how to support oneself sustainably long-term is significant when you’re in the early stages of your artistic career.

Contact Info:

• Website: www.leland-montgomery.com
• Instagram: https://www.instagram.com/lmontgom1/?hl=en

Image Credits
Feature Image – Monica Schipper