Matthew Cherry moved from the practice squad in the NFL to first string in Hollywood His second stint as a TV director airs Sunday on CBS’ ‘Red Line’

The fact that Matthew Cherry was a wide receiver for the Jacksonville Jaguars, Cincinnati Bengals, Carolina Panthers and Baltimore Ravens is the least most interesting thing about him.

He was a star at the University of Akron, where he still holds the school record for most yards on punt returns in a season, with 305 in 2003, the same year he was named second-team All-Mid-American Conference.

But Cherry gave up the game in 2007. He walked away from the Ravens, his final team, with a $30,000 pretax settlement for a shoulder injury after being placed on injured reserve.

His professional career lasted about three seasons — some of it on practice squads, some of it on a roster. It was time for a pivot.

The settlement money helped him move to Los Angeles, where he was just another kid from the Midwest trying to make a go at this Hollywood dream.

He worked at it hard. For 12 solid years, including a stint of unemployment that sent him back home to Chicago to live with mom and dad.

And finally, his grind paid off — and then some. Cherry is now a TV director, an executive at Jordan Peele’s highly successful Monkeypaw Productions, helping to bring some of Ava DuVernay’s vision to life on CBS’ new limited series Red Line and working on an animated short in partnership with Sony Pictures Animation. He also is directing in ABC’s new series Whiskey Cavalier.

None of this came easy. Not when he set up fundraising accounts to finance his first feature film. Not when his mother died suddenly of an aneurysm — after telling him the previous night how proud she was seeing him begin to fulfill his dreams.

For a long time, that’s exactly what they were — dreams.

“I really didn’t even tell people I played ball,” he says now, sitting behind his desk at Peele’s Monkeypaw production compound in the Hollywood Hills. “I look at it how athletes are received when they break into music. People always roll their eyes like, ‘Ah, Kobe’s trying to do an album,’ or ‘Shaq is trying to do a project,’ or I remember specifically Allen Iverson, when he tried to drop an album. Athletes are always looked at weirdly when they try to do something outside of what they’ve been known for, and I was always conscious of that. …

“It helped that I really wasn’t a big name when I was in the NFL either. It made it easier just to be like: ‘Matthew. P.A. [Production assistant] I want to learn this from scratch.’ … Because people will have a perception of you, for whatever reason. In my experience, people assume that former pro athletes aren’t hard workers. Or we just want stuff handed to us, and we’re not willing to put in the work and grind for it.”


Matthew Cherry played briefly for the Baltimore Ravens.

Courtesy Matthew A. Cherry

Cherry grew up on Chicago’s North Side, and the first sport that caught his eye was baseball. He wasn’t a standout athlete, but his dad was a big Chicago Cubs fan, so he stuck with it. His earliest memory of the sport? It was horrible. He couldn’t remember which hand his mitt went on.

But there was always a lesson to be learned.

“I saw very quickly, if you put the time in and you practice, you can get better at it,” he said.

He also was growing. Rapidly. He decided to try football. Although his parents were middle-class, there weren’t enough resources for travel teams. But with practice, he became good enough to catch the eye of the coaches at a private Jesuit school in the northern suburbs, Loyola Academy in Wilmette.

“I very much felt like Fresh Prince of Bel-Air,” Cherry said of his high school experience. “Just being this kid that’s actually from Chicago, a black kid, [and] at the time, it was not diverse at all. I remember my graduating class, we had five black kids in a class of 500.”

In fall 1999, he headed off to Akron, Ohio, and by his senior year he was an All-MAC candidate. Maybe this pipe dream of playing in the NFL — something he never thought seriously about before, as football was merely the means to getting a scholarship — could come to fruition?


He wasn’t drafted. And life in the NFL didn’t look like it looked in the movies, that’s for sure. He was on the practice squad most of his rookie year, until the Cincinnati Bengals signed him to the active roster for the last two games of the 2004 season.

Cherry started thinking of a different plan in 2005. A friend from college called him before training camp of his second season. Cherry had studied broadcasting in college and had worked in campus radio as a music director and on-air personality. He interned at a Cleveland radio station.

“One of my guys that I worked with on the Cleveland radio station, he was like, ‘Man, I’m going to L.A. for the BET Awards. Will and Jada are hosting. We’re doing a live remote there. I don’t know what you’re doing, but we’ll let you kick it with us if you want to come out,’ ” he recalled.

“He listens. I don’t know if that comes from being coached, but he listens. And that’s very rare for a man in this industry.” — Angela Nissel

“In the back of my mind I was already starting to think about what my Plan B was going to be. Because my rookie year, I got cut and placed on practice squad, and that was really the first time I’d ever dealt with a situation like that, where I felt like I was good enough. But because of some of the politics around coming in as an undrafted player, sometimes if you’re not in the right situation, regardless of how well you do, you’re not gonna get a shot,” he said.

Arriving in Los Angeles, “I just remember my mind being blown. The weather. The mountains. The palm trees — but also how the entire city was just based off entertainment. It was all coffee shops, people in there writing scripts. The print/copy place, they’re talking about a discount for headshots and script printing. I was like, ‘This entire city revolves around this industry. That’s crazy.’ I just remember coming back from that experience just being really inspired. And I met this person who knew this other person who knew this other person who had been part of this program called Streetlights … a nonprofit organization that basically helps men and women of color get jobs as production assistants.”

Fast-forward to year three as a professional football player and Cherry is playing for the Baltimore Ravens after stints in NFL Europe with Hamburg and in the Canadian Football League. He had lived in nine cities and three countries in that three-year span.

He’d had enough. And he was ready to see what Hollywood was about. So he got into the production program, and his first job was working on Mara Brock Akil’s comedy series Girlfriends. On his off weeks, he worked on her spinoff series The Game, about a newly minted NFL player navigating his rookie year with his college sweetheart.

He was earning $300-$400 a week. It was low. But he loved it. This was his film school. He got to see how TV directors such as Debbie Allen, Sheldon Epps and Salim Akil worked, used camera equipment, set up shoots.

His next gig was on NBC’s sci-fi drama Heroes, but this time he took some extracurricular initiative: asking if he could use the camera equipment on off days to shoot music videos. He’d scour MySpace and reach out to rhythm and blues artists, offering to direct their music videos free of charge if they could make it out to L.A. He’d come up with the concept and he’d have the equipment — he just wanted a chance to tell a story. He got his first credit in 2008 directing a video for R&B artist Terry Dexter.

His side hustle served him well. He ultimately directed music videos for Michelle Williams featuring Beyoncé & Kelly Rowland, Tweet, Jazmine Sullivan, Lalah Hathaway, Kindred the Family Soul, Snoop Dogg, The Foreign Exchange, Bilal, N’Dambi, Maysa Leak, Dwele, Najee, K’Jon and Chloe x Halle.

Which brings us to now. Cherry has hit the place that he’s worked nonstop for since he arrived in 2007. He’s a creative executive at Monkeypaw. An executive producer on the award-winning BlacKkKlansman and a producer on The Last O.G. for TBS, where he just directed his first episode of TV.

“I thought he was going to be a stereotypical, kind of misogynist-without-recognizing-it, football guy,” said Angela Nissel, the co-executive producer of The Last O.G. “I remember the first time he was on set. Sometimes when you bring things up and there are a lot of guys, sometimes they tend not to hear you. He was the first one to say, ‘Wow, Ang, I hadn’t thought of that perspective. I’m glad we have a woman on set.’ He listens. I don’t know if that comes from being coached, but he listens. And that’s very rare for a man in this industry.”

Cherry’s second stint as a TV director airs Sunday on CBS’ Red Line, an eight-episode limited series about three Chicago families forced by tragedy to think about how race and racial biases affect their lives. The series is executive produced by DuVernay, who encouraged Cherry to write and direct a film about his experience in the NFL years ago. The result was The Last Fall, which aired on BET in 2012 after having its world premiere at the SXSW Film Festival and receiving an award for best screenplay at the American Black Film Festival.


Matthew Cherry (left) with Tracy Morgan (right) on the set of The Last O.G.

Courtesy Matthew A. Cherry

Now, as he thinks about that decade-plus of struggle, Cherry can smile. He met Peele in the midst of the successful run of Peele’s Oscar-winning Get Out. Peele liked a tweet Cherry tagged him in, started following Cherry and later sent him a direct message and asked to meet him. That was 2017, right after Peele announced his first-look overall production deal with Universal and Cherry thought maybe he’d be asked to direct a small-budget film. Instead, Peele wanted to hire him. Peele shared with him in that meeting that he was creating a space where he could continue what he did with Get Out: tell stories that have a social message and use genres such as horror, sci-fi and thrillers to make films and TV that are fun and commercially viable.

One of those projects is TBS’s The Last O.G., which stars comedian Tracy Morgan as a newly released felon who is trying to acclimate himself to society, get to know the twins he never knew he fathered and adjust to the new whitewashed affluence of his old Brooklyn neighborhood. The series also stars Cedric the Entertainer and Tiffany Haddish.

“Jordan really has given me that boost. When I first started working here, I was always looking at it like, man, what are the opportunities for directing? Maybe I can do some shows here and try to get that first opportunity. And The Last O.G. was always on my mind … just really fell in love with that show. The heart that it has, seeing Tracy in a way you’ve never seen him before,” Cherry said.

And for what it’s worth, we’ve never seen Cherry like this before either. He’s in the zone. And there doesn’t appear to be a slowdown anytime soon.

“It just literally felt like all these 10-plus years of being in L.A. and struggling, and living out of my car at some point, all these things you would do just to stay in L.A., stay in the game … if you could just stay here long enough, you might be able to make it,” he said.

He did that as a high school football player trying to get a college scholarship. He found it when he was struggling in the NFL and knew he needed to pivot.

And now, he’s figured it out in Hollywood. That early life lesson was key.

“It really is an athlete thing,” he said. “I would even go back further to that first time I picked up a baseball glove and put it on the wrong hand. Being able to see progress is something as an athlete that’s probably been the most important thing. Knowing that if you work hard enough, if you just stick it out long enough, you’ll get your shot.

“And then when you get your shot, you gotta take it. Or you have to go back to the bench. And that’s just always been a thing that’s been with me. I never felt like I had any opportunities that were just given to me. I’ve always had to create my own opportunity or give my own look or try to figure it out myself. And I just think, luckily it’s worked so far. And I think that’s the biggest thing about being an athlete, is being able to set a goal and knowing if you work hard enough, you can reach that goal for sure.”

Animated short ‘Hair Love’ to show the bond between fathers and daughters Filmmaker Matthew Cherry wants to help ‘normalize’ black fathers

Matthew Cherry’s evolution has taken him from the football field to a stint as a production assistant to music videos. Now, his résumé includes a heartwarming short film in production called Hair Love.

Cherry said the idea for the film came from watching viral videos of fathers interacting with their daughters. In particular, he focused on ones that showed fathers combing their daughters’ hair, which can be both a chore and a bonding experience.

His five-minute animated film is about the relationship between an African-American father, Stephen, his daughter, Zuri, and her hair. Although Stephen has long locks, he is used to his wife doing his daughter’s hair. When she is unavailable right before a big event, Stephen has to figure it out and concludes that Zuri’s hair has a mind of its own.

Cherry said the “story was born out of seeing a lack of representation in mainstream animated projects, and also wanting to promote hair love amongst young men and women of color. It is our hope that this project will inspire.” He took to the crowdfunding site Kickstarter to fund the film. His initial goal was $75,000. To date he has raised almost $252,000, making Hair Love the best-funded short film in the history of Kickstarter.

Cherry, 35, is a former college wide receiver. In his four-year career at the University of Akron, he finished with nearly 2,000 receiving yards and 13 touchdowns. After college, he played for the Jacksonville Jaguars, Cincinnati Bengals, Carolina Panthers and the Baltimore Ravens. In 2007, he moved to Los Angeles to pursue a career in entertainment, landing work as a production assistant.

“I was just Matt the PA, and I was here to work,” Cherry said. “I was here to learn and work the game from the ground up, and that’s how I kind of got my foot in the door.”

He has worked on more than 40 commercials and was a director for more than 20 music videos for singers and entertainers such as Michelle Williams, Tweet, Jazmine Sullivan, Lalah Hathaway, Kindred The Family Soul, Snoop Dogg, The Foreign Exchange, Bilal, N’Dambi, Maysa Leak, Dwele, Najee, K’Jon and Take 6.

Cherry’s film The Last Fall received awards at the American Black Film Festival (ABFF) for Best Screenplay and Martha’s Vineyard African American Film Festival (MVAAFF) for the HBO Best Feature Film Award. After a limited theatrical release, it made its television premiere on BET in December 2012 and is currently streaming on Netflix and Hulu. He recently released a short film, Forward, which premiered on Ebony.com. He also writes and directs the award-winning web series Almost 30 and Almost Home.

Cherry has one sister (visual artist Caitlin Cherry) and grew up on the northwest side of Chicago.

“Sports was a big part of both of our lives growing up,” he said. “I played baseball ever since I was 5. Football ever since I was 6. Played three sports in high school. Had a full scholarship for football in college. … My existence was very much kind of tied into sports growing up.”

Cherry spoke with The Undefeated about his transition out of football, positive representation of black fathers in the media and normalizing black families.


What was your inspiration for Hair Love?

The biggest, and I think the most important, is just we’re seeing a big lack of representation in that computer-generated, animated world.

We really haven’t seen a lot black characters in that space. Bebe’s Kids was the first animated feature film directed by a black director. That came out in 1992; 25th anniversary was a couple of days ago. Peter Ramsey was the first African-American director to direct a CGI [computer-generated imagery] animated film. That was like two or three years ago, Rise of the Guardians. I think in between that time, there’s really only been those two black directors that have done like a full-length feature film in the animated space.

So we only really have had in recent years maybe four or five examples of full-length feature films that really tell our story. But a lot of times you don’t really see the whole, full family dynamic, particularly in these computer-generated feature films. The biggest thing for me is just like really seeing that lack of a presentation. … I don’t have kids myself right now, but got a serious girlfriend, and one day we’re going to get married and be having kids, and I really wanted to make sure that when I did have kids that they had a character that they could relate to.

When you look at mainstream media, and you see all the images, black hair isn’t made out to be the norm. It’s not meant to be the standard of beauty. We have a very Eurocentric standard of beauty in America, and if you watch TV, if you pick up a magazine, if you look at different things, you’re not going to see yourself represented. … You don’t see your curly, kinky hair on these different models, on these different actors and actresses, on these different music videos, etc. It can really do damage to your self-confidence and how you perceive yourself.

That’s why my biggest thing with this project, first and foremost, was just to really hopefully have some characters that were human, that showed black families in a complex but also simple manner, and just have characters that people can relate to but then try to help increase that diversity in the animation world, because representation is everything. I think my biggest thing is if a little girl can see Zuri or see Stephen, and see themselves represented, if it makes them feel better about themselves, to me, mission accomplished.

Who did you consult with about dads, daughters and hair?

I’ve actually had this idea for a couple years. I always thought it would be cute to do a story about a dad trying to do his daughter’s hair. I’ve seen a lot of kind of online videos, and my main dad friends who have kids, they’re always posting pictures and videos online of their failed attempts of trying to do their son’s and daughter’s hair, and just always thought that that would be a really cool angle to hit, particularly because the whole black father angle. I think, again, in mainstream media, we’re really nonexistent.

We look at a lot of these movies and TV shows, they always depict black dads as deadbeats, nonexistent, abusive. These fathers, they’re getting girls pregnant, running off, that whole thing, and while obviously in every race, every group, you have that negativity, but it’s always made out in the black community like that’s just all black men are. We just are deadbeat dads. We’re not in our kids’ lives.

So for me it was just really important to normalize black fathers, normalize black families. And really I think in starring a young black father and his daughter, I think that would just do wonders to kind of help normalize those images, because it’s important.

What’s been the most difficult part of moving from football to filmmaking?

The most difficult part of my journey is feeling like you have to constantly create your own opportunities. Like, to this day, nobody’s ever hired me for anything. All my opportunities have been self-generated in some fashion. Outside the music video world, from feature films to short films, it’s all been stuff that I either created with some friends or I created on my own, and sometimes it gets frustrating because you feel like, ‘I made this. This premiered at a major festival. Help me.’

Help me get to the next level. I did the work. I followed the blueprint. I did everything that they say you’re supposed to do in order to have somebody help you get to the next level. …

You make all these sacrifices like putting your mom’s life insurance money into the making of your first movie. It comes out, hey, you get a little bit of press, but nobody hires you. Damn. OK. You go away for a couple years. You do random things to kind of stay alive. Then my second feature film, 9 Rides. We shoot it on iPhones and that’s the thing that gets you noticed and gets you an agent and then you realize that all the work you and your team put in mattered after all.

They’ve seen us doing the short films for no budget. They’ve seen us doing the music videos. They’ve seen us doing these feature films and all this other stuff, so. I think the biggest, most difficult part of the journey has just been having to continuously create your own opportunities to kind of continue to put yourself in the game, and I think that there’s a lesson in that, in that you can’t predict what’s going to be the thing that hits, or is going to be the thing that helps put you on. You’ve just got to keep working, keep grinding, and eventually something’s going to hit, or eventually someone’s going to help.

Do you miss football?

Not at all. Not in the least. No, I don’t, especially with all this news about what’s been going on with players’ heads and CTE. I’m actually glad that I didn’t play too long. People have been playing since they were 5 years old, too. You know what I mean? Between Pop Warner, high school, college, you might have your five or 10 years in the league, but if you’re 25 you might have played for 20 years.

How did you prepare for your career after sports?

I studied radio, TV, broadcast and media production in college. I interned at a lot of radio stations, and I was the music director at my college radio station at the University of Akron. I interned up at the Cleveland radio stations, KISS and then on WENZ. And so I would always be kind of dabbling in production, but more of an audio-radio side, and it was something I was really interested in. I loved cutting promos, loved working with all these other kind of post-production programs, and I kind of knew even in college that whenever I got done playing ball I’d either be working in radio or some level of entertainment on the production side of things.

I signed as an undrafted free agent. My rookie year with the Jacksonville Jaguars, I knew after training camp, I was like, “Yeah. I’ve got to get my plan B together,” because it was just so political. When you come in as an undrafted free agent it’s like being a walk-on, so all these things have to happen that are outside of your control in order for you to make it. Guys will generally have to get hurt or traded and all these other things. It’s not really about how you perform, necessarily. It’s about, ‘OK, can you justify putting this guy in over the guy we’re paying millions of dollars?’

And I knew literally in training camp like, ‘Yeah. This is kind of unfair. I’m doing my thing, but I’m still not getting rewarded for it on the field.’ I actually got cut during training camp, and then they re-signed me to the practice squad. That’s how they do it, and I learned when I first got cut by just feeling there was nothing more I could have done. I felt like I balled out. I did everything that I should have done to be able to make the regular team, and it didn’t happen for me.

What’s up next after Hair Love?

This has all been a roller-coaster ride. The biggest thing for me is just really trying to just continue to do projects that are personal to me. Things that I really love. We hope to be able to use the characters from Hair Love and turn it into a feature film

This interview has been edited for clarity and length.