There’s is no set blueprint for anyone who wants to pursue a career in directing. No one embodies this notion better than Chicago native and Monkeypaw Productions exec Matthew Cherry. The director got his start as a football player before traveling to Los Angeles to become a Production Assistant. A few years later would breed success for Cherry.

Since then, he’s directed two independent films and his acclaimed animated film Hair Love was picked up by Sony Animation. In addition, he’s directed three of the most acclaimed new shows on television: The Last O.G., The Red Line, and Whiskey Cavalier. Shadow And Act sat down with the intrepid filmmaker to discuss how he got his start and what advice he has for aspiring Black creatives who want to venture into directing.

S&A: Congrats on your success. How did you make the transition from commandeering the football field to commandeering the film set?

MC: When I moved to L.A., after I retired from the NFL, I became a PA. I was a part of this great program called Street Lights, which trains you as a Production Assistant, teaches you about set etiquette. I went through that program and ended up PAing on a lot of commercials, but I also had an opportunity to PA on the TV show Girlfriends in its eighth and final season. It was really there where I saw people who looked like me. There were people of color, Black women and Black men who were directing television. Along the way, I met a lot of great people, like Heidi McGowen, who now works on black-ish and grown-ish. I remember meeting with her a year after we worked together and asked her what she sees me doing. She said she can see me directing. That was the first time somebody ever said it. It was really from that moment, and then getting on Heroes my second year in Los Angeles in 2008, and seeing all Black directors like Anthony Hemingway and Steve Mann who were working on this big sci-fi superhero show [that I knew]. It was a combination of seeing people who looked like me doing it, but also a great mentor who encouraged me to get into it.

I wasn’t the first to do a feature film on an iPhone. Sean Baker who directed Tangerine was kind of the first to do a major feature film shot with an iPhone. But also I knew that it was something different for a white filmmaker to do that and something different for a Black filmmaker to be able to do that. For me, when we were developing 9 Rides, it was really important because white directors shot a lot of films on iPhone, but I couldn’t recall a Black director having shot a major feature with iPhones. It was really important to me. I really wanted people to feel the same way I felt when I saw a director that looked like me inspire me to direct films. I wanted young filmmakers and people who were interested in film. I always try to be open with our budget, which was only $1500. The more of us that are aware that you can shoot a feature film with your iPhone, the better and the more stories we’ll be able to tell. I think it’s all about making it as democratic as possible. The film industry is probably one of the hardest businesses because you need to assemble a big crew and the budget. There are certain things you need for your project to look a certain way and to prove that you can get into a major festival like SXSW.

S&A: Let’s talk The Last O.G., which is from Monkeypaw. You also directed an episode of the series, which stars Tracy Morgan and Tiffany Haddish. What was it like shooting on the streets of Brooklyn?

MC: Jordan Peele and Tracy came up with this idea of a drug dealer who had a heart of gold. It was amazing. Tracy is such a good dude. He has such a pure heart. He’s all about love and making sure the whole crew is just a family. To see Tiffany rise and to work with them both [was great]. Everything about the show is awesome. It was just really an experience being in Brooklyn every day and actually shooting in a lot of these neighborhoods that are being gentrified. We were in Prospect Park and Park Slope. There are so many areas that have been hit hard by gentrification. Shooting on some of these streets with multi-million dollar brownstones with a mostly Black crew was really cool. It was really cool.

S&A: You directed an episode of The Red Line called “We Need Glory For A While,” what was your experience like directing an episode of CBS’ new drama?

MC: I’m from Chicago, so it was awesome going home and being able to direct an episode of TV. It was a little bittersweet because my parents passed away earlier in the 2010s. It was always my goal and it would have been amazing for them to see that. They saw my struggle from being a football player to [becoming] a director. For me, that was just a really exciting moment to be back. It’s also crazy how it timed out to because I ended up getting inducted into my high school’s hall of fame for football around that same time. I wrapped shooting on a Thursday and got inducted on Friday. What was really cool was that my grandmother, who is in her late eighties, was able to come to set and check out the project. She watches a lot of TV but is not familiar with the process. Seeing her there was really everything.

S&A: For Whiskey Cavalier, you directed the episode “Spain, Trains and Automobiles”. How was shooting a show with more action different from shooting The Red Line and The Last O.G.?

MC: The thing about Whiskey Cavalier is that it’s very much a character driven show. It just happens to have a little genre webbed into it with the explosions and car chases. It really is a show where character is at the center of it. You have a guy like Will Chase played by Scott Foley, who wears his heart on his sleeve. You also have Frankie, who Lauren Cohan plays, who is kind of the opposite of that. She’s more closed off and insular. You’ve got an amazing cast with Tyler James Williams and Ana Ortiz. It was just really an awesome experience and the action just really stood out from the character moments. It made me think of how you can use action to further the story. It was awesome because that was my first time shooting action. It had an incredible crew, great tech unit directors and stunt coordinators. That was my first time ever being in Prague. I was one of the few people of color in that country, let alone on that set. To be in charge of a set like that was pretty crazy.

S&A: What advice would have for a Black person who wants to pursue directing?

MC: My biggest mistake was probably trying to follow other people’s journey. Seeing how a lot of these directors got into directing when I was PAing, I talked to them and tried to see what they did. One of the guys went to the ABC Director Fellowship Program, so I applied to that and never got in. If you talk to 100 directors, you’re going to hear 100 different stories of how they got their shot. Some people do a big feature film and people come to them with jobs. There’s really no rhyme or reason to it. You just have to run your own race. A lot of times we get frustrated because we see other people’s accomplishments. We see them doing well and get frustrated. Just run your own race and be ready for when the opportunity comes. Just keep learning and keep growing.

READ MORE:

‘Hair Love’: Sony Pictures Animation Picks Up Matthew A. Cherry’s Short Film

‘The Last O.G.’ Season 2 Trailer: Tracy Morgan And Tiffany Haddish Are Back For More Shenanigans

Photo: Larry D. Horricks/ABC via Getty Images

9 Rides

Get relevant content delivered to you once a week