“Your Pain Is Your Gift” Screenwriter/Producer-Star Michael Tennant on ‘Pretty Problems’

Michael Tennant grew up in San Diego with a “disdain” for Los Angeles. “You’re taught the Dodgers are the devil,” he jokes. “LA is the worst. Don’t do this. But my brother did a play, I heard him get a laugh… and that first hit of dopamine, I started chasing that. I liked the idea of performing.”

In the early days, Tennant wanted to become an actor. “Good Will Hunting was a seminal movie,” he says. “These two guys just got together and wrote something? And Gus Van Sant is directing it? Robin Williams is starring in it? How did these guys do that?”

Tennant says he somewhat lost track of that and focused on acting. “I got stuck in the linear idea of it for a while, but then I fell into producing.” While on set one day, a producer had lunch with Tennant and this led to work in development. “I saw the sausage getting made and it made me kind of sad.”

Tennant adds, “I was watching people set money on fire, never their own, but other people’s money, making movies for the wrong reasons. After a few years reading thousands of scripts, I thought I wanted to give writing a crack. Let me see if I can do this.”

Inspired originally by Matt Damon and Ben Affleck, and more recently by the Duplass Brothers (see the speech, “The Calvary Isn’t Coming”), Tennant knew he needed to take his shot. “I keep asking other people — writers, directors, casting agents — to hand me this creative life that I want and no one is doing it. Why is no one doing it? Because you have to do it yourself.”

The Cavalry Isn’t Coming

“I think inherently, as an actor. If you do this long enough, you maybe become a writer without realizing it. I would not compare myself to a proper screenwriter or someone who has studied the craft and spent time in the writers’ room, but I like writing dialogue and banter. Then it’s like, okay, I have to force story on top of this.”

Tennant still considers himself more of an actor, even though he has written this screenplay, Pretty Problems. “I wrote all of the male roles for myself with the expectation that you can maybe grab someone on hiatus or someone with a break in their schedule between Marvel movies and ask them, ‘Hey, do you want to be in my indie movie about feelings that is kind of funny?’”

Assuming he would play a smaller supporting role and land a more well-known actor for the lead, the script was ready just before the pandemic. But one night at dinner, while looking at his “chosen transplant family” of actor friends, he decided he already had the cast he needed. “It would be so cool to make a movie with these people. It’s going to be scary and maybe no one will watch it, but we know these people and we trust these people.”

“As an actor, you fight so hard to get two lines on Law and Order, and your whole belief system is like, ‘I’m good because I booked Cop #2’ versus ‘I’m good because I’m a good person and I care about things and I love my craft.’ But we no longer work in a binary system of just an actor. You have to wear multiple hats and you have to be comfortable being a hyphenate.” 

Above all, there’s a major difference in sending out a screenplay and committing to getting a movie made. “I think they’re all lottery tickets. If you get in entertainment, it’s a lottery ticket career and you are a lottery ticket. And that’s terrifying.”

Television Vs. Indie Film

“There’s a huge difference between indie Film and television. In television, there are so many hurdles and so many people have to stamp it. I would tell anyone not to shoot their pilot presentation. I know it worked out for Always Sunny, and those guys are heroes of mine, but we talk about it because that happened one time.”

That said, he does encourage other creatives to make their own shorts and perhaps their own features to send to festivals. Specifically, he’s saying not to attempt first projects where there are countless gatekeepers in your way. The real problem with this approach is that you are spending your own money and hoping someone is going to buy your pilot. 

“Honestly, people lack creativity when they watch things. They think, this is all this can be. It’s the reason actors go to commercial auditions dressed as doctors. They want to showcase, this is what I would look like as a doctor. Write a pilot. It’s fun. You find your voice. But there’s a financial risk doing TV. You’re better off telling a closed-ended story.”

“You can make a short for $1,000. It’s not going to look like Avatar, but it’s you. You’re going to meet people who love Film and want to support you. The reason I’m making my next movie is because we did a successful run with Pretty Problems. I’m making my next movie because someone in Maui loved my movie and wants to help me tell more stories. Sending your story out into the ether is a lottery ticket.”

“As a former development executive, we read about 8 – 9 pages of your script. If we’re not in by then, we’re out, because there are so many things coming in. I would encourage any creative to make their own stuff. Greta Gerwig did that right with Barbie. She’s working in the system now, but none of that happens if she wasn’t doing mumblecore movies fifteen years ago. Start creating and see where the road takes you.”

“Everybody is reading the same books on screenwriting. No shots at Save the Cat, but they teach you formula and structure, which is important, but you are the only person who can tell your story. You have to be realistic about it. Don’t write about robots fighting dinosaurs. Trust yourself. The only person there for you is you. Hold yourself accountable.”

Write What You Know

“I think you should write what you know. This movie was very much a shared experience for me. I could feel my marriage wasn’t doing great. I was talking to a lot of my friends about the way their relationships weren’t working — male and female. I was looking at my work life and I started to get obsessed with the idea of potential. The problem of writing what you know is that you have to get big with it.”

Tennant adds, “There’s this Rick Rubin idea that your pain is your gift. The thing that makes you sensitive or the thing that makes you unique in the world is your gift. But exposing that gift is really hard because we don’t want to open our veins up for people. And you have to be cautious about how you open your veins up for people.”

Michael Tennant

The screenwriter knows he’s a “sensitive person and a talker,” and that’s always the approach he uses to sell himself to others. “I agree with ‘write what you know’ as long as you are comfortable changing what you know and understanding why you are feeling the way you are feeling. If you’re just writing what you know, those are plays. If you’re willing to get in there, get vulnerable, get ugly, that’s where the magic really is.”

For this particular project, in addition to opening his veins, he nerded out on indie film. “I nerded out on Indie Film to try and notice what was working. Everybody loves The Big Chill and everybody has tried to rip off The Big Chill, but there’s a reason why they don’t work. You have six of the greatest actors of all time and the greatest soundtrack of all time. That’s very hard to duplicate.”

“What does work is singular locations, where everybody is trapped in one place. What’s that level of tension? I was also thinking about vacation relationships. On vacation, you and your partner want to fix everything. ‘Vacation Me’ is great. He’s going to do it. He’s going to get the six pack. He’s just there and existing, but ‘Real Life Me’ has to walk the dog and get on the phone and then the day is over.”

Digging deeper, he continues, “Honestly, being totally vulnerable, I was trying to save my marriage. I made a comedy about a marriage that wasn’t doing so great because I wanted to tell people a story where a spoonful of sugar helps the medicine go down. I never thought we would win festivals. I never thought we’d be in movie theaters. That blew my mind.”

Closed-Ended Storytelling 

As someone who wants to make indie comedies, it drives Tennant crazy that Comedies have essentially moved to action comedies. “I really enjoyed the movie Game Night, but then they flip a plane at the end of it. Why? I just enjoyed the awkward conversations. People are making a big deal out of No Hard Feelings, but we used to have those movies in theaters all the time.”

“Pretty Problems was honestly tough for me. I maxed out some credit cards. It was self-financed. I sold a lot of shit to make this movie. Partially going back to Do the Right Thing. If this is how I have to make this movie, this is how I have to make this movie. When I showed this script to people, nobody cared.”

The screenwriter says even their sales agent wasn’t interested in reading the script. “Our sales agent didn’t want to take it on. It was a comedy about a bunch of thirty somethings on a vineyard for a weekend. There’s no foreign sales opportunity. Then, when we finally got him to watch it, it won the Audience Award at SXSW and now people were fighting over it.”

“I’ve shown this movie all over the country. I’ve watched audiences in Alabama laugh at jokes that people in San Diego didn’t find funny, but we’re not that far apart. We listen to the loudest voices in the room and get polarized, so it’s been cool to be a part of something that is just connecting people.”

The struggle of carrying this boulder up the hill to make a film means facing rejection again and again. “Imposter syndrome is real. I felt we got into SXSW because I had done my homework. Then we won the Audience Award, but we marketed the shit out of the movie. We manipulated that. But then it keeps going and you have to ask, ‘Did we actually make something good?’”

“I still don’t think of myself as a writer. It’s weird to be having conversations about writing. But I know that’s what gets in my way. It’s me telling myself No when the world is telling me to pursue it. In therapy, your relationship to you is all that matters. If you’re listening to critics, you’re not listening to yourself at the end of the day.”

This interview has been condensed. Listen to the full audio version here. 

by Brock Swinson

Freelance writer and author Brock Swinson hosts the podcast and YouTube series, Creative Principles, which features audio interviews from screenwriters, actors, and directors. Swinson has curated the combined advice from 200+ interviews for his debut non-fiction book 'Ink by the Barrel' which provides advice for those seeking a career as a prolific writer.

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