From Kickstarter to Kickin' It At the Oscars: Matthew A. Cherry and Karen Rupert Toliver Talk Hair Love

Matthew A. Cherry and Karen Rupert Toliver attend the 92nd Oscars Nominees Luncheon on January 27, 2020 in Hollywood, California.
Matthew A. Cherry and Karen Rupert Toliver attend the 92nd Oscars Nominees Luncheon on January 27, 2020 in Hollywood, California.
Photo: Kevin Winter (Getty Images)

Animation raised me.

Yes, I know we all grew up watching Saturday cartoons and animated movies, but those little doodles of Roger Rabbit and Mickey Mouse shaped my desire to tell stories. I wanted to create animated films. I wanted to be Cree Summer. I wanted to have anything and everything to do with the celluloids that had such a stark effect on my imagination. While I don’t have the technical expertise to actually create and draw the cartoonish characters swirling in my head, I most certainly respect those who do. Seriously, that shit is a very long and arduous process. Please hug the animator in your life.

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Speaking of the process, let’s talk about Matthew A. Cherry and Karen Rupert Toliver. Oops, I have to introduce them properly—Oscar-nominated Matthew A. Cherry and Karen Rupert Toliver.

The last time The Root got to sit down with Cherry, he was knee-deep in a Kickstarter campaign hoping to bring a longtime idea to life. That idea had been shelved for years, but it was the spark from seeing several viral videos featuring black fathers doing hair that truly set things into motion.

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Hair Love is more than a film. It is more than a book. It is the buoyed confidence of a little black kid. It is the flickering screen commanding the rapt attention of a little black girl who sees herself. It is the collective embrace of a young loc’d black boy discriminated against at his school. It is the ally of a progressive law.

I am always a fan of following “untraditional” journeys in this industry and Cherry is certainly an example of that. Leaving the NFL in 2007 to pursue a film career, Cherry became the second former professional athlete to be nominated for an Oscar. The first was the late Kobe Bryant, for Dear Basketball.

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“I think it’s just a testament to anybody who has more than one dream, or working in a day job and they have a dream that they want to pursue,” Cherry mused. “It’s never too late to pursue your passion, and the more life throws at you, the more careful you have to be about your planning. But, it can happen. And there’s no rule that says it has to happen before you turn 30. There’s no rule that says you only can live out one of your passions. It can happen. We’re a living testament.”

Studios spend millions of dollars on Oscar campaigns; marketing is a very significant component in a film’s chances of winning that statuette. However, Cherry has mastered organic social media marketing in a way that has everyone talking about #HairLove as a Twitter trending topic.

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“When [Trump] got elected, it was like a light bulb for me,” Cherry noted, adding that people like to engage with you as a “person” more so than someone who simply markets a product. “If you’re not saying anything, you’re complicit. It just felt like a great time for everybody to stand out and speak up. It was a combination of [that and] sharing my journey as a filmmaker, transitioning from the NFL to a P.A., working my way up in the film industry, sharing opinions on current topics, [whether] political or entertainment. I always look at social media, particularly Twitter, as a creative outlet to work on my writing and to express myself. You have to be very concise with your opinions and your views. You can do it in a funny way to increase the engagement. And I took pride in that.”

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Though Cherry is deservedly getting a lot of shine for this achievement, it was the moment I saw the name “Karen Rupert Toliver” on my screen as Issa Rae (who also voices the mother in the short film) announced the Animated Short Film nominees that became something extra special for me. With a hopeful “please be a black woman, please be a black woman” mantra bouncing around in my head, I rushed to Google her name and found pictures of this face:

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Then I saw her title: “Executive Vice President of Creative, Sony Pictures Animation.”

And. I. Squealed.

I sat there, mouth agape, looking at an animation executive who just became an Oscar nominee and she is a black woman. As such, my very first question to Toliver had to be about being a gatekeeper in this industry. Oftentimes, without black people being in the position to uplift our content, our content is erased.

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“This is a business of filmmaking, but it’s also an art,” Toliver said, as she reflected on the beginnings of her career as the one black representative in the room to now, where she holds “weight” and responsibility to make a real difference. “You write what you know, you draw what you know, and that definitely pertains to everyone. When there’s not people there that are like you, then when you’re doing something that’s personal and reflects you, then maybe they won’t get it because it’s not part of their experience. So, when Matthew came to me with this idea, it was a no brainer. It was a joy, because one, it was something that I’d never seen before in animation and two, it reflected everything about my hair experiences, black men and the black family. If there’s not somebody in the room that has that personal connection, they may get it from a theoretical [stance] or knowing it’s the right thing, but it’s not personal. And that’s how a lot of these things get made.”

And much like Cherry is represented in the father character, Toliver certainly sees herself, too.

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“My mother had lupus when I was in high school,” Toliver recalled, noting her mom’s diagnosis invoked a fear of losing her own hair. “So, she lost all of her hair. She was bald. I saw her at home [with her] bald [head] and she would put on a little wig when people came over.”

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“All of the images of hair in our short touch on so many different emotions, memories and feelings about our [self-]expression,” Toliver added.

So many emotions, indeed. One of them is joy for two black animated filmmakers on their way to the Oscars. From its humble crowdfunding beginnings to the Oscar red carpet, Hair Love is certainly the people’s film. And we’re rooting for it. Hard.

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The 92nd Academy Awards will air Sunday, Feb. 9 at 5:00 p.m. PT/8:00 p.m. ET on ABC.

Staff Writer, Entertainment at The Root. Sugar, spice & everything rice. Equipped with the uncanny ability to make a Disney reference and a double entendre in the same sentence.

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