In 2006, Matthew A. Cherry was a wide receiver struggling to get playing time in the N.F.L., bouncing between teams and getting signed and cut again and again.
After injuring his shoulder and being placed on reserve for the Baltimore Ravens, he was ready to move on. Using the Hollywood Creative Directory, he looked up three Black showrunners in Los Angeles and mailed letters to each of them asking for a job.
Then, he packed his bags and drove to Hollywood to pursue his dream of becoming a filmmaker.
Sixteen years later, Cherry has worked his way from production assistant to successful writer-director. In 2020, he won an Oscar for “Hair Love,” an animated short about a Black father who struggles to style his daughter’s hair while her mother is hospitalized. Now, he has an animated sequel series on Max, “Young Love,” which follows the same young Black family in Chicago; it premiered on Thursday.
Although Cherry feels that he has finally made it in the industry, he still seems a little surprised at how he got here.
“My whole career I’ve been going in through back doors and building doors where there are no doorways,” he said.
On a recent Thursday, Cherry ambled through Central Park on a break between TV interviews about “Young Love.” He is tall and athletic, but he is also a nerd, gushing about seeing Lin-Manuel Miranda in the audience at Shakespeare in the Park and rattling off the names of filmmakers he admires.
Born to a mother who worked as a legal secretary and a father who worked in a factory, Cherry grew up in Albany Park on the northwest side of Chicago. He and his sister would often visit their grandmother and eat home-cooked fried chicken and mac and cheese in her big brownstone in a mostly Black neighborhood on the West Side, where “Young Love” is set. He took an early interest in sports, but he also became fascinated with music and movies, starting with obsessively rewatching a Winnie the Pooh movie.
“We rented it so many times from the video store that the owner just gave it to us,” he said.
In high school at Loyola Academy, a private school in a northern suburb, he participated in a radio and TV club and was one of five Black graduates in a class of 500. He was also good at football — very good — and earned a full-ride scholarship to play at the University of Akron, in Ohio. While there, he nourished his twin passions for sports and entertainment, studying radio and TV broadcast and media production and becoming a music director of the college radio station.
Nick Sparks, Cherry’s college roommate and former teammate, remembers him being a “tall skinny wide receiver from Chicago” who was always on the go, networking with people in the entertainment world or holed up in the campus radio studio.
Cherry lit up the field in Akron. He set a school record for most yards on punt returns in a season and was named Second-Team All-Mid-American Conference in 2003. Suddenly the N.F.L. seemed within reach. He joined the Jacksonville Jaguars as an undrafted free agent in 2004.
His N.F.L. career, unfortunately, “was not your typical millionaire story,” he said. Over the next few years, he was shuffled around the league and played in nine cities and two other countries, trying to land a long-term spot on a roster. But even as he struggled in the league, he continued to keep up with the entertainment world.
“He always had the latest music and latest videos,” said Chris Thompson, a running back and Cherry’s former teammate on the Jaguars. “He was one of the first guys to put me on to Kanye West.”
By 2007, frustrated by how his peers were advancing in the league while he stagnated, Cherry retired from the N.F.L. and decided to pursue his other longtime dream, to work in entertainment. He relocated to the San Fernando Valley, north of Los Angeles, crashing on a friend’s couch while looking for work.
With the help of Streetlights, a nonprofit that helps people of color get jobs as production assistants, he landed his first job as a production assistant for “Girlfriends” and later worked on NBC’s “Heroes.” At the same time, he would search Myspace and message R&B artists offering to make music videos for them. He didn’t own recording equipment, so he got permission to borrow cameras from the “Heroes” set for his own music videos.
In 2008, he directed his first video for an R&B artist named Terry Dexter, and he eventually directed videos for Jazmine Sullivan, Snoop Dogg and others, sometimes making only $100 a day. He also directed TV episodes and scripted shorts, and he wrote and directed two feature films: “Last Fall” (2012), about an N.F.L. player struggling with life after football, and “9 Rides” (2016) which was shot on an iPhone 6s.
“He’s not traditionally trained as a filmmaker,” said Monica A. Young, who has worked as a producer for Cherry on many of his projects. “He learned on the job.”
Then Young, who had been producing for Cherry since 2008, got an interesting call from him in the fall of 2016.
“Hey Mon, I have an idea,” she recalls him saying. “If we do it right, we can win an Oscar.”
Cherry’s idea was to create an animated short about a young Black girl’s hair. At the time, the animated film space was still dominated by mostly white characters, and he wanted Black kids to be just as well-represented.
“My whole life I never really had those characters that I could look at onscreen say, ‘Wow, that’s me,’” he said.
What resulted, “Hair Love,” which Cherry wrote and co-directed, was a resounding success; in addition to its Oscar, it became the basis for a best-selling children’s book and the inspiration for a line of Dove Kids hair products.
With “Young Love,” Cherry wanted partly to showcase the parts of Chicago — and the people — that viewers don’t normally see onscreen. The show picks up after the events of “Hair Love,” with Angela (voiced by Issa Rae) out of the hospital and Stephen (Kid Cudi) working to succeed as a music producer. Together, they raise their daughter, Zuri (Brooke Monroe Conaway), and deal with the challenges of paying rent, parenting and managing their careers.
“I’ve never really seen a family show that centers on millennial parents, young parents that have tattoos and dealing with health issues and lack of insurance and all the things that we are dealing with today,” he said. “We really wanted them to represent a new age of parenting.”
For Cherry, the show is also about showing a Black man onscreen who isn’t an absent father, who is deeply involved in his daughter’s life — the kind of man Cherry wants to be for his 11-month-old daughter, Theory. (Cherry met his wife, Candice, who works as the head of film at Kevin Hart’s production company, at the American Black Film Festival in Miami in 2016.)
He recently showed the trailer for “Young Love” to Theory, and he said she likes gazing at the “Hair Love” picture book, even though she is too young to read.
“She’ll be there holding the pages, flipping through them,” he said. Sometimes, he’ll pull out his phone and take a photo — a memory of young love preserved for the future.
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