Former NFL wide receiver Matthew A. Cherry made it in the mecca of gigs and glamour with an Oscarwinning film marking diversity in the world of animation. We ask him how he did it.



WHEN MATTHEW A. CHERRY decided to make the transition from being a wide receiver for the National Football League (NFL) to pursue a career in the entertainment industry, he had no idea he would become “one of only 39 people of colour to ever win the most prestigious award in Hollywood”. 



Last year, he won the Oscar for Best Animated Short Film for Hair Love, a story he had written and directed about an African-American father attempting to do his daughter’s hair for the first time. Born in Chicago in the United States (US), Cherry began his early childhood playing sports and had big dreams of becoming a professional sportsman. He fell in love with football by the age of six after a brief stint with baseball. 



At the time, he had no idea how much the sport would change his life. Football got Cherry a full scholarship to study at the University of Akron in Ohio, and through that, he got his first big break; being drafted to the prestigious NFL, where he would spend the next couple of years playing for the Jacksonville Jaguars, Cincinnati Bengals, Carolina Panthers and Baltimore Ravens. 



“I was always interested in film, in entertainment in general and music and I knew really early on that I wasn’t going to have a long career in the NFL and decided to retire probably a lot earlier because I got tired of moving and travelling the world in that way. I ended up retiring in 2006 and then moving to Los Angeles in 2007 to pursue a career in film and TV,” says Cherry in an interview with FORBES AFRICA from the US over Zoom in March. 



His hope at the time was to become a TV director but like many chasing the dream in Hollywood, Cherry had to earn his stripes. He had the opportunity to cut his teeth as a production assistant after meeting an alumnus of a program called Streetlights, a non-profit organization in Los Angeles (LA) that helps men and women of color find jobs as production assistants behind the scenes. 



“The inclusion efforts were nowhere near where they [are] today. I would often work on jobs, be it TV shows or whatever, and there would be 150 people in the crew and I would be the only one, two or three people of color in that crew. It was hard for people of color to break into the industry unless you went into film school or had industry connects and I had none,” says Cherry. 



Slowly but surely, he began to make a name for himself by shooting music videos for Beyoncé, Kelly Rowland, Michelle Williams, and many others before transitioning to live-action short films. 



“In 2011, I did 11 music videos and directed my first feature and then a couple of years later, like 2013 and 2014, it was really dry and you try and figure out what your next move is. The thing about LA is if you put your effort into a project and that project doesn’t hit a certain way, you are back to the drawing board. Just because I did a music video for Beyoncé doesn’t mean the next job is going to be as well-paying or fruitful and so it is a constant struggle.” 



In a city famed for its glitz, glamor and garish mansions where ordinary people can morph into celebrities with millions in their Louis Vuitton suitcases, there is an illusion that you strike it big and rich instantly. Cherry is quick to correct this notion. 



“You are always on the grind and the hustle for the next gig and I have never been in a position where I don’t know how much money I am going to make this year. Just because you work in January, it doesn’t mean that you are guaranteed a job in February and there are times where I was like ‘I don’t even know if I am going to be able to make rent’ and that is very stressful in that regard. Everyone in Hollywood is hustling, trying to make it to the top and sometimes to the detriment of others and it is a very cut-throat world,” says Cherry.



 Throughout his 14-year “hustle” to breakthrough in Hollywood, the accomplished sportsman in him pushed him forward in those dark days. And he was not wrong to bet on himself. According to leagueside.com, “only 8% of the top 1% of the top 1% of high school football players will make it to NFL”. And Cherry was one of them and all he needed was that breakthrough project to convey this to Hollywood. That eureka moment happened while he was watching the Oscars one particular year.



“I’ve always watched the Oscars and that’s the biggest thing in Hollywood and I am always trying to see which black people are winning and in 2015, I was paying attention to every category and I am seeing awards being handed out for categories I didn’t even know existed, like sound mixing and sound editing, documentary short etc. 



“So, I remember seeing animated short category and they won an Oscar. They got up, they gave a speech and they got the same Oscar as the one that won Best Director or Best Actor.” 



It just so happened at the time that Cherry had an idea floating around in his head about a dad and his daughter. 



“I hadn’t told anybody yet. After the Oscar [ceremony], I called my manager and I said ‘I have an idea and if we do it right, I think we can mess around and win an Oscar’ and that is how I felt and she said ‘ok, let’s figure it out’.” 



A viral tweet about an Afro-Latino dad and his daughter was all the proof Cherry needed to know he had a potentially amazing idea. 



“I realized that a big reason why the numbers were higher was that people didn’t look at this like it’s a normal thing. We always assume that mums will be the ones doing this and mainstream media always assumes that black dads don’t support their kids. And that is because you don’t get a lot of great depictions of dads.” 



With that information, Cherry got connected with a great illustrator and developed a really strong campaign and took to Kickstarter to raise the funds to produce his first animated short. 



“I have used Kickstarter to raise money for both of my previous shoots and with both previous ideas, we barely reached $15,000. Hair Love raised $3,000 within an hour and I hadn’t even shared it with everybody yet. Then we raised $15,000 the first day and we hit our goal of $75,000 in five days and $300,000 in total when we ended the campaign and we became the highest-funded project in Kickstarter at the time,” says Cherry. 



And the rest as they say is history. The film gave Cherry the much-needed credibility and pedigree one needs to make it in Hollywood. 



“I felt a lot freer because I knew after struggling for 13 or 14 years, things will get a lot easier in terms of half the battle, like trying to get into the rooms and trying to get people to take you seriously. Something like that happens to you and you are in the next meeting and it’s a totally different energy and instead of people wondering ‘are you capable of doing it’, people are now giving you the benefit of the doubt.” 



Cherry has now signed an exclusive first-look deal with Warner Bros TV and is currently in the process of developing another animated series, Young Love, based on the characters from Hair Love, making him one of the most sought-after black directors in global entertainment today.

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HOLLYWOOD. HUSTLE. AND HAIR LOVE