Pretty Problems: Michael Tennant Reveals His Film’s Cinderella Story (Exclusive)

While today’s production process is relatively expedited, many films go through an especially extensive process before making their way to consumers. That was the case for Michael Tennant’s Pretty Problems, a new Hulu comedy that was first conceptualized over five years ago. Tennant, the star and screenwriter of the project, penned the script in the years that followed, setting an April 2020 start time for filming, but pandemic precautions forced Pretty Problems production to delay just as it was about to roll cameras.

“We called the entire casting crew and said, ‘Hey, everybody stay locked down for two weeks. We have this compound all to ourselves. The people that own this house are gone for for three weeks. We have three weeks to shoot the movie,’” Tennant told ComicBook.com. “And then, a year and like 14 months went by because we all just stayed locked down.”

Production couldn’t commence, but Tennant and his support cast kept the project’s momentum rolling in a virtual capacity.

“During that time, I think partially to stay sane, we did a lot of table reads on Zoom,” Tennant continued. “We did a lot of improvising. You need to trust that what you’ve got is going to work.”

Tennant’s insistence on bringing Pretty Problems from concept to reality boiled down to it being a “prove it” project for his career.

“I just have spent so much time waiting for directors or for casting directors, or for agents or for managers or whoever to hand me this creative existence that I want so badly,” Tennant added. “I think it was 2018, I was at South by Southwest and I saw [filmmaker] Mark Duplass give his second iteration of The Calvary Isn’t Coming speech. I would suggest it to any creative, any filmmaker, any writer or anyone really. It’s just about the idea that you keep waiting for someone else to show up and rescue you and no one’s coming. The only person that’s going to get you out of the rut you’re in is you. I think this isn’t just for artists. I think this is for all us.”

He didn’t know it at the time, but that 2018 trip to South by Southwest ended up being the first step of a full circle moment for Tennant. Pretty Problems was brought to SXSW in 2022.

“South By was always the festival I wanted to get into. I’ve had movies play at really major, major film festivals, but this thing was so inherently mine. I made it with a bunch of my friends. We were the only movie in our category that didn’t have a movie star in it,” Tennant said.

The Cinderella story for Pretty Problems only continued when SXSW eventually came around.

“They gave us our first screening time. It was 11:30 in the morning on a Monday, the first weekend of the festival. Everybody’s already gone. Most of the press is gone, all of the celebrities are gone. They put us in this huge theater and I was like, ‘We’re f–ked. No one’s going to show up. We’re in a 450 person theater. No one knows who any of us are,’” Tennant recalled. “We bought 300 pairs of pink heels. We put QR codes in them. We ran all over Austin. We were paying Uber drivers to keep them in their cars. We were hanging them in restaurants. We’re going to get people to come see this movie. Then we showed up and there was a line around the corner to get into the movie. The reviews came out, and the reviews were amazing. And it still didn’t feel real.”

Tennant’s Hail Mary efforts paid off, as Pretty Problems went on to take home the SXSW Film Festival Audience Award, Narrative Spotlight.

“It still felt like we’d gamed the system or something weird was happening,” Tennant said. “Then we continued to like win awards and go to other festivals. We got bought. We were in movie theaters. I finally had to have a conversation myself about like, ‘This is real. You accomplished this.’”

Pretty Problems is streaming now on Hulu.

Editors note: This interview was conducted prior to the SAG actors’ strike.