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.”
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.
“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.
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.”