NFL to Hollywood: Northwest Side native Matthew A. Cherry’s ‘Hair Love’ makes Oscars’ short list

When Matthew A. Cherry’s plan to make, and stay on, an NFL roster fell through, he knew it was time to enact his Plan B: break into the film industry.

“That was the first time where I was good enough, but it didn’t work out ...,” Cherry said. “At that moment, I was like, ‘It’s not even about ability; this is about politics and a whole bunch of other stuff that’s outside of my control.’ I started to think about my Plan B in a real way.”

That plan has Cherry, a filmmaker, director, and writer, on the cusp of an Oscar nomination.

His current project, “Hair Love,” an animated short film about an African American father who attempts to do his daughter’s hair for the first time, was recently named to the animated short film list for the 92nd Academy Awards.

“Hair Love,” which was shown in theaters with “The Angry Birds Movie 2,” debuted in August.

“You have a situation where Mom may have to go into work early and Dad has to get the kids ready,” Cherry said. “... The gender norms that existed back in the day aren’t really the same as they are now.

“I feel like everyone has to step up and get it done. Black fathers have had one of the worst raps in mainstream media as being portrayed as being deadbeats and not being involved.”

Cherry, 38, grew up on the Northwest Side playing Pop Warner football at Portage Park and baseball at Gompers Park.

He later attended Loyola Academy in Wilmette, where he was inducted into the school’s Athletic Hall of Fame. While at Loyola, he played three sports: football, basketball, and baseball, while being a member of the school’s Radio and TV Club.

Next, Cherry attended the University of Akron on a football scholarship, where he majored in radio/TV broadcasting.

As of 2019, Cherry continues to hold the school record for most punt return yards in a season.

After leaving the NFL, where he had stints with the Jacksonville Jaguars, Cincinnati Bengals, Carolina Panthers and Baltimore Ravens, he started working his way up on music videos from a production assistant to director, a process Cherry calls a “project to project progression.”

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His film, TV and music video credits include directing well-known musicians including Michelle Williams, Kelly Rowland and Beyoncé, Snoop Dogg and Common.

Cherry’s first feature film, “The Last Fall,” which made its debut on Netflix, details the trials and tribulations of a professional athlete who tries to achieve his dream of playing in the NFL. The film won several screenwriting and directing awards/nominations.

A year before the film was released, the NFL locked out its players after the league and the players’ union couldn’t agree on a new collective bargaining agreement.

“The thing I noticed was that everyone was pretty much on the owners’ side,” Cherry said. “Most fans say, ‘Why should I care if an NFL player gets a million dollars, or $2 million? That’s more than I’ll ever see in my lifetime.’ ... Every team has four or five players who make big money; everyone else is trying to figure it out.”

Cherry has directed episodes of the TBS series “The Last OG” with Tracy Morgan and Tiffany Haddish and the Chicago-based CBS drama “The Red Line” from executive producer Ava DuVernay.

He was an executive producer on “BlacKkKlansman,” a film directed by Spike Lee that won the Academy Award for best adapted screenplay. Cherry also worked at Jordan Peele’s production company Monkeypaw (“Us,” “Get Out,” CBS All Access’ “The Twilight Zone”) as a film and television executive.

“This was something I knew I wanted to do beyond football,” Cherry said. “If I didn’t make it, I’d retire and move to New York or L.A. and try out my second career.”

The nominations for the 92nd Academy Awards are scheduled to be announced Jan. 13.