“Two Distant Strangers” follows a day in the life of cartoonist Carter James (Joey Badass), a young Black guy trying to get home to his dog the morning after a promising first date. When a totally benign encounter with a police officer goes south, he finds himself back in the woman’s bed after a brutal shooting. Each morning he tries to escape his fate in ever more creative ways, and each morning he wakes up in the same place after his waking nightmare.
This tragic cycle overlaid onto the plot of a beloved ‘90s comedy makes for a fruitful juxtaposition, and the film dances between comedy and drama like a lyrical freestyle. Free began his career as a standup and has written late night for the last six years, on “The Daily Show” with both Jon Stewart and Trevor Noah, as well as “Full Frontal With Samantha Bee.” While he initially thought the film would be more satirical than it became, his natural humor brings a thread of levity throughout. “It didn’t wanna be really funny. I kinda just let it come out the way it came out,” Free said during a recent phone interview. “Once I was looking at it on the page, it felt right, it felt like this is what this story wants to be. So we embraced it, and our goal from that point on was to film it in a way that made that tone and that structure work.” Free knew the ending would seal the tone for the film, and he grappled with how exactly to pull it off. In Carter’s increasingly inventive attempts to outrun his tragic fate, he eventually lands on the debate method. He tries explaining the whole “Groundhog Day” concept to his murderer, hoping to appeal to the cop’s humanity. The tactic appears to work, and the cop ends up driving Carter home to protect him from any other dangers. As the camera focuses on their friendly handshake, the film seems to be winking out at the audience, tempting us to fall for the ruse.
“I sat with what I wanted the ending to look like,” he said. “Because I knew from the beginning there’s no way to end this movie that buttons up the reality of what we live in. There’s no solutions to this problem in the real world that anyone has actually thought of that works, so I can’t present one in this movie.” After six years in late night, Free is excited to explore more narrative storytelling. He and Issa Rae are shopping “Him or Her,” a TV project about a Black bisexual guy inspired by his own experience. He’s also exploring bisexuality in a new project yet to be announced, which follows three former child actors adjusting to adult life. While writing on HBO’s “Camping,” Free said Jenni Konner’s mentorship was invaluable to building the confidence to make the jump. He shadowed her, went to meetings, and even ran the set for part of a day.
“It really was like a showrunners’ class,” he said. “And it really did change my life in terms of how I looked at scripted television. It also made me realize how few people get that opportunity.” In the months following the swell of Black Lives Matter protests last summer, many companies across all industries committed to supporting racial justice causes, whether through recruiting initiatives, donations, or community outreach. In Hollywood, Black creatives suddenly found themselves very in demand, with many feeling bombarded and suspicious at the outpouring of opportunities. From his perspective, Free and his colleagues benefited from the uptick, but he feels the enthusiasm has died down. “I know a lot of people who got jobs and offers for things because people were trying to wake up to what was happening, and there has been a cooling off,” he said. “In some areas in some industries things have gone back to normal, and people forgot how charged up they were last year when it was at the forefront of everyone’s mind.” In addition to the potential for an Oscar nomination, Free is proud “Two Distant Strangers” is getting attention now because it will keep people from forgetting about George Floyd and the urgency they felt last summer. (While an official release is still in the works, an Oscar nomination would certainly ensure a high profile distributor.) “It was one of the biggest stories in the world and now you almost never hear about it…I want people to be reminded what happened last year was not just important to Black people, it was important to the world, it was important to a lot of people,” said Free. “‘Two Distant Strangers’ reminds you that last year happened and we can’t ignore it and we can’t forget it.” Sign Up: Stay on top of the latest breaking film and TV news! Sign up for our Email Newsletters here.
