Robert Townsend is not the brash young upstart he once was in the 1980s. He just recently turned 59, and no longer frequents the comedy clubs where he started performing decades ago. But after a four-decade stage, film and television career that includes the indie hit Hollywood Shuffle and collaborations with Eddie Murphy, Denzel Washington and Halle Berry, the affable multi-hyphenate stays busier than ever.

His latest movie, Playin’ for Love—in which Townsend plays a high school basketball coach smitten with the mother of his star player—arrives on DVD this month. And several more projects are in the fire, including a one-man show Townsend is writing with acting guru Ivana Chubbuck, as well as a planned a remake of the 1985 Richard Pryor comedy Brewster’s Millions. (The new version will be called Brewster’s Billions.) “I always try to find movies and stories that resonate with me,” says Townsend.

EBONY: Playin’ for Love has an interesting backstory. Tell us about it.

Robert Townsend: Here’s what happened. I was in Miami a few years ago for the American Black Film Festival when I was approached by Michelle Spence-Jones, the commissioner of Overtown [one of the city’s oldest neighborhoods]. Michelle said, “All these kids are dying by violence and gangs and drugs. We need to do something to motivate them.” She said, “Could you teach them about making movies and make a short film with them or something?”

So being from Chicago and the ’hood, I said, “Instead of a short, we can make a whole movie!” [laughs] And that’s how this film started. Michelle told me the city had funds to help make the movie. They would give us access to schools and things. And I said, “There’s a script I wrote some time ago that I think would be perfect.”

EBONY: So this was very real grassroots filmmaking.

RT: Well, yeah. The whole community got involved. For eight weeks, I talked to kids about how to make movies. Then the kids got to be in the movie. They got to work on the crew, in the hair, makeup and wardrobe departments. All the kids in the program also got an executive producer credit on the film.

EBONY: I heard you held basketball tryouts at the American Airlines Arena in Miami. How did you swing that?

RT: As the community effort came together, we reached out to the Miami Heat. Dwyane Wade donated sneakers for all the basketball players in the movie. Pat Riley and the Heat organization gave us the American Airlines Arena to have our auditions and we had 5,000 kids show up. At the tryouts, Isiah Thomas, who’s also from Chicago and a producer on the film, put the kids through basketball drills that are used in the NBA. That dude was hard! [laughs]

EBONY: Was the tryout where you found the actor who plays Justice, Daniel Yorel Cooper, one of the nation’s top basketball recruits?

RT: He was one of the 5,000 that came out to audition. It was really my daughters Sierra and Skye that cast him, because they were like, “Daddy, he’s fine.” [laughs] “And he can play basketball.” My daughters were kind of like my scouts. Daniel came in to read and there were all these other guys that we were looking at and my daughters were like, “Daddy, you’re missing it with him. You know, the Afro. The look works, Dad.” So that’s how he got cast.

EBONY: Speaking of family, this is a very family-friendly movie. It has positive messages about parenting, teamwork and the necessity of academics for athletes with dreams of turning pro one day.

RT: You know, anytime I make movies I like to add a “Trojan horse” to the story. I think entertainment can give you the opportunity to say things [about who we are], because when we go to the movies, we look for answers to our lives. We ask ourselves, “How would I deal with that situation, or what is going on here?” So I try to incorporate how I feel about [some of the fundamental questions raised by the movie], but I try to do that in a funny way and sometimes in a dramatic way.

EBONY: Were there any sports movies or romantic comedies you looked at for inspiration?

RT: The one that I looked at—and it’s a film that’s always in my heart—was Claudine. That was the first movie I fell in love with as a kid and bought the soundtrack to. Claudine had James Earl Jones and Diahann Carroll. It’s the story of a single mother of six kids who falls in love with a garbage man. It was close to my mother’s story, and mine too. [My mother] was a single parent with four kids and, you know, is there a man who’s going to date her?

EBONY: I noticed that you cast Lawrence Hilton-Jacobs in the movie. He was one of Claudine’s kids, and also played Cochise, the teenage basketball prodigy in Cooley High, another classic ’70s film.

RT: Yeah, well, because of Claudine I asked Lawrence to do me the favor. This is an homage to the single mother, so Lawrence agreed to do a cameo. I was really honored to have him, because the very first film I ever did when I was 17 was Cooley High. I’ve got two lines in that movie. If you look at Cooley High, I got this big Afro parted in the middle and I say, “I got Cochise on my side” and “Somebody ought to kick his ass.” Those are my first two lines on screen. 

EBONY: Early in your career, you did a lot of theater work before you turned to standup. How did you hook up with Keenen Ivory-Wayans, a co-writer and co-star on your breakthrough film, Hollywood Shuffle?

RT: When I [moved from Chicago to New York to do comedy], Keenen was the first one to work with me and help me. Keenen was already a regular at The Improv when I was doing standup and he kind of got me into The Improv.

EBONY: You’ve said that Hollywood Shuffle—a skit-driven comedy that lampoons the movie industry’s stereotypical casting of Black actors—was partly based on your own experience as a young actor in the 1980s. Do you ever wonder what it would be like to go on auditions today? What would your Hollywood Shuffle character Bobby Taylor have to say about Hollywood in 2016?  

RT: I was just having this conversation this morning with an executive. It’s a different time in Hollywood. On one hand, you’ve got Shonda Rhimes, with Scandal and How to Get Away With Murder, and BET, TV One, Centric TV. There are all these networks and images of Black life that are different from what we had before. But we still need more movies, and movies of real quality. That’s why you have this whole [#OscarsSoWhite] thing and people are talking about boycotting the Academy Awards.

EBONY: How bad is the problem?

RT: Something like 250 movies come out of Hollywood every year. Out of those 250, maybe six or seven target the African-American audience, and from that seven, maybe three are Oscar material. You see what I’m saying? So if Bobby Taylor was around now, he’d say it’s not a bad time in Hollywood but it could be much better.

EBONY: After the success of Hollywood Shuffle, you went on to work with a lot of very high-profile actors. What was it like to make that leap? 

RT: When you work with talented actors, they all have that same kind of hunger to make something special. So when I work with, say, Halle Berry or the last movie I did with Michael Clarke Duncan, they just give you everything, because they know how important movies are. I’ve always been in heaven. Everybody I’ve worked with in my career—James Earl Jones [Meteor Man] or Denzel [Washington, The Mighty Quinn]—there’s a certain work ethic that they have that I’ve always admired and I love.

EBONY: When you look back on your career, which of your movies do you feel best about, and which do you feel didn’t achieve what you wanted?

RT: Here’s the thing: All my movies are my babies so [laughs] I can’t pick one. As an artist, I’ve always tried to paint on as many different canvases as possible. I never duplicate myself. If I look at Hollywood Shuffle, I go, Oh, I love the satire and silliness. When I look at The Five Heartbeats, I love the music and the heart of these guys and this family that breaks up. [Ed. note: Townsend is currently working on a documentary about The Five Heartbeats, and is celebrating its 25th anniversary with a special screening at the Writers Guild of America later this month.] If I look at Meteor Man, I go: “I’m a kid! I’m a kid and I can fly!” Holiday Heart, you know, tells the story of a non-traditional family. So when I look at my movies, they’re all different. I think, as an artist, you always want to be true to yourself and have fun. And throughout my career, everything I’ve ever created, I’ve had fun.