Exclusive Interview: Writer-Producer Kevin Gillese Talks ‘How to Ruin the Holidays,’ Creating Visibility in Media, the Film’s Timely Themes, and More

Meet the incredibly talented Kevin Gillese, a jack-of-all-trades in the world of entertainment—acting, writing, producing, and directing all under his belt. But what sets him apart is his knack for creating much-needed visibility through his craft, which is evident in his debut feature as a writer, How to Ruin the Holidays.

In this soon-to-be classic, we follow the hilarious escapades of Michelle (played by the fabulous Amber Nash), a struggling comedian who reluctantly heads back home for the holidays. Her sister Andrea (Kate Lambert) insists it’s an emergency, but their doomsday-prepping dad and laid-back brother Mark (Luke Davis) aren’t buying it. As the family gets ready for what might just be their last Christmas bash in their family home, Michelle embarks on a mission to redefine her connections with her quirky father and siblings. Throw in her dad’s offbeat lifestyle revelation, and Michelle faces a life-altering decision about taking care of her brother with disabilities.

Pop Culturalist was lucky enough to speak with Kevin about How to Ruin the Holidays, how he hopes the film inspires others to think differently, and more.

PC: How to Ruin the Holidays was inspired by your relationship with your brother, told through a comedic lens. It’s so different from how these sibling dynamics are usually portrayed in the media. How early on did you know you wanted to tell this story in this way, and why was that so important to you?
Kevin: I’ve always wanted to do something like this, but I didn’t know if I would ever be able to. I guess I was maybe a bit scared of getting it wrong, so I let that fear subconsciously hold me back. But when I made the short film, which was an awesome experience and on YouTube, I met Luke, who plays the role inspired by my brother in that project. He was so good, and I loved working with him. I thought, “Oh, wow. I finally found an actor through whom I could try to tell some of these stories.” That was really the seed. It was meeting Luke. Through that first project, we really dove into this world, and it went well. I felt good about it, and I thought, “I’ve got to keep going with this.”

The reason it’s so important to me is that it’s a truthful reflection of my lived reality. When I didn’t see that in media, I felt like there was a gap that I could contribute something to that means something to me.

PC: Everybody feels perfectly cast in this film. As you were penning this script, did you have these actors in mind? How did knowing what they were capable of influence how you wrote for them?
Kevin: The majority of the parts were written with someone in mind. Not every single role, but the leads for sure, and a lot of the secondary roles. I like writing with people in mind because you can go to the next level beyond just writing a good character with funny lines, being three-dimensional, interesting, and truthful. You’re also thinking about what types of roles does this actor usually play. Am I going to lean into that type or away from it?

PC: You’re opening so many doors for these actors. The film strikes the perfect balance between comedy and heartfelt moments. Was that something you were mindful of as you were writing it? The comedy genre really lends itself to improvisation. How were you able to create the space for these actors to play and take ownership over their characters?
Kevin: I’m such a softie. I really am. I come by it with honesty. I’m a real heart-on-my-sleeve guy. For better or for worse, I like to put my characters into situations that are heartfelt and then use that tension that comes from drama or emotion to spring into a joke. That’s just what I like to do.

As for improvisation, it’s wild because we had no money on this movie. It was the most low-budget thing ever. [laughs] We didn’t have a lot of time. That’s the thing that really costs low-budget films—the time. But that means we don’t have as much time for improvisation as we wanted. That didn’t stop the cast. [laughs] They improvised some of my favorite moments in the film. At the very end when they’re driving away, the neighbor is watching them go. In the script, he was supposed to have this long monologue where he says, “I’ll never meet anyone like you again.” But then Henry [Zebrowski] just says, “Who am I without you? I don’t know that man.” It was so much funnier. I’m lucky that we got great improv moments out of all our cast.

PC: It’s a testament to you as a writer too because you don’t let audiences sit with one emotion for too long. It’s been a long road bringing this project to life. What’s been the most surprising part about this journey? What does it mean for you to see how this project is resonating with so many?
Kevin: This is my first film, so I was learning as I went about a lot of things because I wrote and produced it. It was learning the business of film. Somebody gave me the advice that every phase is the hardest phase. I thought, “There’s no way that’s true!” That cannot be true because they told me that when I was fundraising. I was like, “This is impossible.” But it’s true, it really is true. When you think it can’t get any harder, you get to the next phase, and you’re like, “Oh, this is much harder.” That’s been surprising to me. I knew it was going to be challenging, but I come from the world of theater and comedy. I was like, “How much harder can it be?” It’s harder. But that makes it all the more rewarding to get to the finish line and get it out in front of people.

I’ve been getting messages trickling in throughout the month. I was just reading an email from someone who was like, “We’ve been watching the development. We donated to the Kickstarter years ago. Now it’s finally being released. A member of our family just passed away, and we all watched the movie together, and we loved it.” The fact that they would message me that really says to me that they do feel connected to it. That’s so rewarding.

PC: Like you were saying earlier, you have a background in theater. On the stage, you get reactions and responses immediately. But filmmaking is such a long process, and it can take years before audiences are able to see it. You were lucky enough to have the Atlanta premiere where it was shot. What was that experience like? What was your favorite behind-the-scenes moment?
Kevin: The Atlanta screenings were awesome! They were the best. People were so enthusiastic and excited. There were big laughs and cheers. It was a wild night, although I had a bit of a hangover the day after. [laughs]

My favorite behind-the-scenes moment is one of our executive producers, Chris Escobar, is also the owner of the Plaza Theater. He’s the executive director of the Atlanta Film Festival. He’s a leader in the scene in Atlanta. We were playing at his Plaza Theater, and he got this little photo booth. The director and I were pacing around, and we were really nervous. He was like, “Hey, hop in.” He sticks us in the photo booth and sticks a dollar in. He’s like, “We’re getting some pictures. You have to remember this moment.” I was like, “That’s so smart.” I really appreciated the gesture. It was a sweet moment.

PC: Speaking of Arlen [Konopaki], you’ve worked with him in the past. What were those earlier conversations pitching him this script and having him direct? How have you two been able to push each other creatively?
Kevin: Working with Arlen, there’s so much trust there because we’ve been a comedy duo on stage since 2005. We’ve seen it all. We’ve seen the biggest comedy festivals. We’ve seen the tiny crappy little gigs, and everything in between. We’ve seen our bodies get old and frail over the years. We’re coming up on twenty years. I trust him. It would have been really hard for me to hand this film to a director that I didn’t have that level of trust with. But because I did have that level of trust, I was like, “I’m giving you full creative leadership. This is yours now.” Ultimately, this is our project. It’s a project that we did together. When I was writing it, it felt like mine. Then when we got into production, I handed it over to him. It felt like his, and ultimately it would have been really scary if we didn’t have that trust because it’s such a personal script. But we do have that. That mixture of emotion and humor is something that we do on stage, so I knew that he would understand how to play with that.

PC: That’s the beauty of filmmaking, it’s that collaboration. I really believe you have a holiday classic on your hands. The film is out now. Is there a particular scene that you’re really excited for audiences to see? What do you hope they take away?
Kevin: I hope that audiences take away a lot of things. I hope that people with developmental disabilities feel seen and portrayed. I hope that the general population who may not know what they’re walking into, walk away with a broader understanding of what it means for someone to have this type of disability. Because the portrayal in the media has been pretty narrow. I want people to go, “Maybe I can broaden my thinking.” But I hope in general that people realize that the way that things have been done, the way that everyone’s always told us it has to be done, isn’t necessarily how it should be done. We can create new ways of doing things the way that we think it should be, even if that looks a little different than what we’ve always thought.

PC: Outside of this project, what’s next for you? Have you started writing a sophomore feature?
Kevin: I’ve been working on a few different things. It’s funny because if I had known what I know about filmmaking now, back when I started this last project, I don’t necessarily know that I would have even done it because it’s too hard. So now that I know a bit more, I’m like, “Well, I have to make sure it’s this and it’s that.” My education in being a film producer has almost slowed me down because I want to do things in the smartest way possible. I’ve got a few different things that I’m working on, like a mockumentary because I love improv. I’m working on a horror project because Amber and Henry really want to do a horror film. We’ve got a few things.

To keep up with Kevin, follow him on Twitter and Instagram. Stream How to Ruin the Holidays today!

Photo Credit: Ryan Parker Photography