Matthew A. Cherry, who grew up on the Northwest Side and graduated from Loyola Academy in Wilmette, isn’t nervous about being up for an Oscar Sunday.
“I feel like we’ve already won because our short film has touched so many kids,” Cherry says.
His six-minute film “Hair Love” — a tearjerker about an African American father attempting to do his daughter’s hair for the first time — is nominated for best animated short film (watch it on YouTube here).
“I plan to take it all in, enjoy the night, have fun,” he says of the star-studded evening at the Dolby Theatre in Los Angeles.
Cherry plans to bring his fiancee Candace Wilson-Olensky, his younger sister Caitlin Cherry and Deandre Arnold — a Texas teenager who recently was in the news after he was told he needed to cut his dreadlocks to comply with his high school’s dress code, or he’d be barred from his graduation ceremony.
“I would have loved for my parents to be here for this, but they passed away almost 10 years ago now,” Cherry says.
His mother, Diana, was a secretary for the Chicago law firm Mayer Brown, and his father, Kenneth, worked for Fel-Pro, which was a gasket manufacturing company in Skokie.
Cherry graduated from Loyola Academy in 1999.
“Loyola, at the time, wasn’t the most diverse school,” says Cherry, who grew up near Lawrence Avenue and Pulaski Road in Mayfair. “They’ve made strides since, but it’s always made me want to make sure my work was really inclusive and representative.”
He went to the University of Akron on a football scholarship, majoring inradio and TV broadcasting and bouncing around for several teams in the NFL as a wide receiver before retiring from football in 2007.
After that, Cherry moved to Los Angeles and, starting out as a production assistant, worked his way up in commercials, TV, music videos and films.
In 2017, after news stories and viral videos about young black people being singled out for their hair styles, Cherry wrote “Hair Love.” He says he hoped the animated story would “normalize” black hair and portray the positive role black fathers play in their kids’ lives.

Matthew A. Cherry’s six-minute film “Hair Love” is about an African American father attempting to do his daughter’s hair for the first time.
Sony Pictures Animation
Power couple Gabrielle Union and Dwyane Wade contributed to an online fundraising effort to get the film off the ground.
“We take great pride in our hair, just like everyone else does, and there shouldn’t be rules that try to regulate it,” Cherry says.
He says he’s never faced problems over his hair, which he mostly wore short when he was growing up. But he says he was racially profiled once as a teenager when he was out for a run in his Northwest Side neighborhood.
“I got stopped by the police for no reason,” he says. “Someone probably thought I’d stolen something and was running away.”
His resume in film isn’t thin, but “Hair Love” — which he also directed — has brought him a new level of attention. And though it hasn’t been a financial bonanza, he says it has helped opened some doors.
He directed an episode of the ABC TV series “Black-ish” that’s set to air Tuesday.