INDIE SPOTLIGHT: An Interview with SXSW Short Film ‘Dear Mama’ Director Winter Dunn and Screenwriter Charmaine Cleveland

Set in the 90s in South LA, a family grieving the loss of their beloved mother and wife pack up their home in hopes of putting the past behind them. Tanisha (played by Mikayla Lashae Bartholomew), a young, artistic rap fan, tries to hold onto the last pieces of her mother the only way she knows how – a camera she once owned. Meanwhile, Nate (played by Garland Scott), unable to come to terms with the death of his wife, buries them in work in hopes of numbing the pain. While Nate might think he’s doing God’s work by keeping the family afloat, he’s actually stifling his daughter and the two are constantly at odds. Soon, the breaking death of a musical icon Tanisha and her mother once held dear, sparks a confrontation between the two. Tanisha’s need to feel closer to her mother by attending the rapper’s vigil is challenged by Nate, who must learn that people grieve in different ways. Tanisha and Nate are forced to confront the ways they’ve been hurting each other, before taking the first steps to heal. 

Dear Mama director Winter Dunn and screenwriter Charmaine Cleveland created a moment in time both visually and emotionally - and pack a nuanced journey about grief and the relationship between father and daughter in this short film. Every frame, every beat, every look has a poignant place, thanks to its precise direction by Dunn. 

I had the distinct pleasure of speaking with Winter Dunn and Charmaine Cleveland about the collaboration and development process for the short film that was a part of the Film Independent Project Involve, their personal approach to the material, and the type of stories they're drawn to tell. Plus, they both share invaluable advice for those interested in or about to shoot their first short film.

This interview has been edited for content and clarity.

Sadie Dean: Charmaine, is there a personal connection for you to the Tupac song “Dear Mama” or was there a specific time during the 90s that you really leaned into to develop this story?

Charmaine Cleveland: Yeah, one of my earliest memories was sitting at the gas station and hearing that song, after Tupac had passed away, I think I was six and I just remember everybody discussing it in my neighborhood - he was a God in terms of rap music. And so, from when I first heard of him at that age, his music started to take on a lot more meaning for me as I got older and was dealing with some of my own life experiences and grief. At the beginning of COVID when I lost my grandmother, I was just constantly resonating with Tupac's music as like my emotional catharsis and how do I translate this to a film? And how will people resonate with it? When I was in development, I decided to use a mother figure because my grandma was a mother figure to me, and I felt like a lot of people could relate to that. And in a way, it was sort of my thank you to her.

Sadie: That's beautiful. With this initially coming up through the Film Independent Project Involve, did you two initially come in as a team, or were you paired up later on?

Winter Dunn: We all came in as individuals, in individual tracks. And then they started developing, I want to say you all were developing for about eight weeks with the executive track. And the directors are kind of just like bird's eye view, listening in, but not really being able to give too much feedback. And then about a few months in it got time to be like, ‘OK, what projects are you going to start pitching on? Your voices are going to become much more prevalent in the development process,’ so we really need to figure out who are the teams, so they can start really grounding their films as a team. So that's how we came together. I had just made a film about a father-daughter dynamic, and I thought that there was more room to explore that relationship. And I thought, anything that connects Black women to hip hop music in an interesting way, I felt like, my voice would fit. I think it was a really authentic merging between us as creators and the story that was kind of coming out. So yeah, once we were paired up, that's when our development as a team really started and we really started honing like, ‘OK, we're shooting this thing, what is the specificity of it? Where can we pull back and take things out? What is our core? What is our spine?’ And that process, I think, was really fulfilling for all of us.

Sadie: How long was that process from you getting on board Winter to further developing it with Charmaine and then shooting it?

Winter: I would say we developed for about four to six weeks together. And then there's this whole process where now the script gets passed over to the Director and they get to take a pass at the script. So, then I did a couple of rewrites over the course of maybe three weeks, and then two weeks from locking draft, we were shooting. It was a relatively long development process. But I think that it really served us because I feel like once we got on set, every part of our team was so grounded. We were like, we know this thing, we have torn it apart every way we can. It felt like production was really easy, because we really had taken the time to nail the story.

Sadie: Which is so important. And for you Winter, in terms of building your team from your DP to production designer, which is so prevalent in this film, too, what was that getting that team together?

Winter: I was really blessed. Mike Maliwanag was accepted into the program in the DP track. And so of course, I'm looking at all the cinematographer's work and trying to figure out who had the right tone. And as soon as I saw Mike's work, I was like, ‘OK, this kid has something so interesting about his camera.’ It feels like his camera is like living in the world, like a documentary almost. And I was really excited by that. And then we met, and he was like, ‘I actually was at an event with you, you spoke on a panel, and I was going to come say, hey, but it was madness.’ And we have all these mutual friends. And so that was like, done. Nailed it. We're making this film together.

And then Coleen Chen, I want to say it was our producer Nicole had worked with Coleen and she brought her on for both production design and for wardrobe, which in hindsight was probably not the best choice because our film is so period piece heavy. It was nuts - like Charmaine was so gracious with her time - she came on as like art assistant and I was like, ‘I have an art background, I can help decorate Denise's room!’ It was really collaborative, but I think Coleen, as wild and as overwhelming I think as it was for her, she did do a really beautiful job of embracing the period. I told her, ‘I want subtle 90s. I don't want millennial Instagram 90s that we're all doing right now.’ I wanted to feel like you're really walking into your house when we were kids. And she was so great about finding these tiny little touches that were just spot on enough but not flashy, that I think really just cemented the world in a really beautiful way.

Sadie: And then in terms of the casting process with both the roles of the daughter and father, Charmaine were you also involved in helping find those right character voices with Winter?

Charmaine: This was my first short film, so I defaulted to Winter. She was really phenomenal in terms of just getting what I wanted. All of these characters were based on my family and my neighbors. And Nate was taken from my father and Brother Smith was my neighbor growing up, Tanisha was my cousin. And so, Winter did a really good job with that.

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Winter: Yeah, we had an incredible casting director. We really took our time when hiring a casting director, because I knew that that person was going to be a huge creative collaborator for this film specifically. I was like, ‘It's not going to work if the actors aren't right. It's too quiet. It's too simple. If they can't really immerse themselves into this space, it's not going to play.’ For Tanisha, at least 30 tapes, we had girls as young as like 11, really young girls, all the way up to early 20s, who could play younger and she found Mikayla, she went to a reading of a play in LA and she was like, ‘Hey, I'm going to send you options, but there's this girl Mikayla, I think we should just do a director session with her because she's working and she just wrapped King Richard with Will Smith.’ So, we had gone through all these tapes but the moment Mikayla and I got on that Zoom session together, it was like, ‘You're my girl.’ I have a theater background, she has a theater background. I was like, ‘I want to like dig into this text. I want to take our time with it.’ And she was like, ‘I'm game. Let's do it.’

And then Garland, he kind of popped out of nowhere as well. I think he sent us a tape. He was so grounded and so quiet in the way he played frustration and I thought, ‘Ooh, the two of them together, bouncing off of each other. I think it would just be really lovely.’ I think we got in some ways really lucky. But in other ways, we really fought to find the folks who could find the nuance in this really quiet piece. I'm really grateful to have them. They were amazing.

Sadie: Why was it important for you as a storyteller to highlight and dig deep into that father daughter dynamic with this story?

Winter: I think we don't have enough films surrounding Black family in a really universal way. I think telling a story rooted in Black family with these really universal themes is something I'm just passionate about in general. And I think that's why when Charmaine was starting the script, I immediately was like, ‘Oh, I could tell that story, that already fits my aesthetic.’ But I think, there was something really special about watching these two characters, trying to navigate grief together, and really failing to do it as a family together. I feel like as a kid, I really relate to Tanisha, that feeling of like, I have so much to say, I'm not an idiot, right? I'm not the dumb kid in the back that doesn't realize what's going on. I think she sees her dad is overwhelmed with grief, and he's getting lost in this move in the process. And she's like, ‘If you would just talk to me if you would just sit down, and we could just connect on it, we could get through it together.’ And so, I thought that was really special to show this maturity in this young woman, just trying to express herself really, and just hitting these blocks every step of the way, and the frustration of that, because I think a lot of kids feel that. It's like, you have to follow the rules of the household, you have to do what the parents say, but what if that doesn't really fit who you are? Why aren't you included in the conversation? What do you need in this moment? How can I be of service to you? I have a checklist of things I need for you to do for me. I just thought it was something really special there and I don't think we've seen it enough. So yeah, that's what kind of drew me in.

Sadie: And what about you Charmaine?

Charmaine: It was really important for me to get to show this strong father figure that was struggling with something. And as I grew from a child to an adult, and began to realize that adults are not perfect, you see them as your gods almost. And it's like, they have their own struggles they're going through, they're just trying to stay afloat. And sometimes as kids, we don't see that, and then sometimes as adults, they don't understand the things that we're going through. And how are we bridging that gap? And how do we begin to understand each other? And that was a struggle, I felt like a lot of people can relate to. I particularly faced this with my dad, and we're now just rekindling kind of our relationship as father-daughter in a different way as both adults and coming to that understanding and epiphany for me.

Sadie: I’m sure that process was very therapeutic for you. As a writer, and hopefully, you're going to be writing more, are there themes that you're really drawn towards that you want to explore?

Charmaine: This is my first short film project and the first project I ever got produced, so it's so exciting for me. And I'm still kind of trying to find my personal voice and what I want to hone in on. I really love family stories. But I also really love horror. [laughs] I come from a television space and lately have just been working on television projects. But I think my next step is going to be exploring, potentially looking to see what elements I can take from this to make it into a feature, or maybe looking at some horror stories that I'm potentially going to pursue in the next couple of years.

Sadie: I’m just going to go out on a limb here and say I feel like you've found your voice because what you did was so vulnerable and now knowing that personal connection behind it, it is hard for a writer or even a director to tap into that vulnerability right out of the gate.

Charmaine: They don't tell you how hard it's going to be. I definitely cried during our martini shot. I didn't think I was this attached to the project. But if they would have been like, ‘Write about a purple elephant,’ it would have been easy. And then you know, you could just pass it on and see it filmed. And then it's like you're not attached to it. And in television, a lot of times, you write based on what the studio wants and what commercially people are going to consume. And so, this was my first project where they're just like, do whatever you want, which I was not used to that at all. And that was a really awesome learning experience. And they made us go through these sessions when we first started where it's like, ‘OK, talk about what motivates you as a writer. What were your life-changing moments?’ And then you're like putting it all out there. They're like, ‘Great, now write about it.’ You feel almost naked. And then you put it out there for the world, like SXSW was the first time a large audience is seeing it. And you're just like, ‘Oh my gosh, my heart is exposed.’ But that's why it was really awesome to have Winter, she just was so gentle with it. I couldn't have even imagined how beautiful it would have been.

Sadie: Winter, do you have any feature projects in the fire right now?

Winter: It's funny, I'm in like this weird space where I'm taking meetings, and I'm getting scripts, which is such a blessing, right? It's like, I have been dreaming to be in this position where folks are like, ‘I want you to make my work!’ And I'm like, ‘Oh, my God.’ I'm in that right now, reading stuff, really trying to be specific about what a debut feature would be for me. I really want to stay true to my voice. But also, I just think there are a lot of things that feel more commercial coming in. And I'm like, is there a way for me to take my grounded approach and bring it to this story and maybe somehow merge it and find something in the middle? I don't know. So, it's a new journey for me that I'm excited about. And I'm also exploring episodic stuff, getting some shadowing opportunities in TV and commercial work. I feel like for the last few years, it's been work so that you could be in this position, and then start the work again, in this other tier. So, I feel like I'm like starting this new chapter, which is really exciting. I think it'll be beautiful work though, whatever it is. [laughs]

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Sadie: And speaking of journeys, I'm so curious about your individual filmmaking journeys. What inspired you to go down this path, Winter?

Winter: I have an arts background. I've been in art school since the sixth grade; it was like my savior, because I felt very awkward growing up and very misunderstood. I was an only child in this single-parent household, so I was alone a lot, which I think helped me to be in tune with who I was because I spent so much time with myself that sometimes in school, I felt kind of odd, like I don't even know where I fit. And the arts were always the place that helped me find community. So, I was a dancer for years. And then I found theater in high school at the Chicago Academy For the Arts and ended up going to Fordham University in New York for theater. And that's where I started acting, but also directing and I graduated and was like, ‘Hey, I have these images in my mind and I need to figure out how to put them out in the world.’ And something about LA drew me - I think it was the fact that I could have a car and not be on the train. [laughs] Something about it, I was like, I could be more collaborative in that way. I got here and I really just hustled, I put myself on every set I would be invited to. People would be like, ‘Do you produce?’ I'm like, ‘I produce absolutely, sure.’ [laughs] I started producing like web series’ and eventually got offered to produce a super indie feature, which was insane, and that had a beautiful run. And that kind of showed me like, OK, working with a black woman who's a writer-director, and watching her just authentically making the story and just trusting herself, I think really empowered me to do the same.

So, I then went off and made my own short film Junebug, which had a really cool festival run. And then I made some editorial stuff for Condé Nast. And I've just kind of been like that person, I'm kind of a hustler. If you put me in a space where I can learn and create, I will absorb everything in that space has to offer me. And I think that's really served me even with this Film Independent program where we were doing everything over Zoom. It was really terrifying for me, because I'm very much like in the room with my collaborators type of person just being in that theater background space. I was like, I want to grab everything. Like, why are we telling this story? I just want all those little nuance bits because they enhance the work and I think you start feeling it, but you don't really know where all that specificity really is coming from. I think it's coming from actively pulling everything out of your collaborators because, without them, you can't make the film. So that's kind of how I got started. And that's kind of my approach now. I just enter the space like a student and I absorb everything I can and just trust that the work will be impactful if you stay grounded in it and just do the work.

Sadie: For you, Charmaine, and what was the thing that got you hooked into writing for TV and now short filmmaking?

Charmaine: I have a journalism background, I was bumping around trying to figure out what I was going to do. I toyed around with criminal justice for a while and interned for Interpol, I just didn't fit into that community. And then I realized I really like stories, and I love writing, but I also want to get paid for it. [laughs] So I was like, I'll get my BA in journalism, and spent a couple of years doing that, and just talking to a lot of people learning about their stories and their backgrounds. I moved to LA a couple of years ago, thinking I really want to be in the creative space and see if I can make something of this in an even more meaningful way, because I have things I want to say as a writer. And just hustled and did a bunch of odd jobs and had a lot of crazy stories, and eventually, after a couple of internships with Disney and Film Independent, I was able to get into the program and start creating. And then I would say what really drew me to filmmaking, I was trying to figure out what to do and I was living in DC, I didn’t know what my next move was going to be, I don't see myself in law enforcement. I started watching a lot of films, particularly Justin Lin's Better Luck Tomorrow. And I thought the storytelling was so beautiful and unique. And I went looking for more films like that, and I didn't really see a lot, especially featuring a fully Asian cast or a full minority cast. I'm like, ‘This is so cool. But who's making these projects?’ And it was like, no one else is, so I thought it would be cool to pursue this and start doing it myself.

Sadie: Make the films that you want to see. Any advice for those who are starting out on their first short film?

Winter: I would say first, get out and do it. I think a lot of us are still stuck in our heads. And we're so terrified of it not being good, that we take way too long overthinking it. And sometimes you got to do it to figure out what you didn't do right and what you can do better next time. So that would be the first thing I'd say. And then I think if you're really trying to make a strong short, or want to make something that does a festival run or gets that kind of attention, short films, I've learned every second needs to serve a purpose. So as much as you can hold on to what does this person want? How does every single scene show them going for what they want? And how do we see them not getting it or getting it and then how does that want change? Because I think my first short, which I love, I think it's a beautiful film, but in hindsight, I do see where I'm like, ‘OK, yeah, we could have trimmed that 30 seconds, that wasn't necessary,’ or like, ‘Yeah, this little beat really didn't serve the scene. I think it was just a really beautiful visual moment that I loved because I'm more of a visual storyteller.’ Make sure every scene is serving the purpose, like what do we want? How are we fighting for what we want? And I think programmers will really respect it, because it's that specificity. Every second serves a purpose.

Sadie: Get in get out, especially with short films because you don't have a lot of time.

Winter: Exactly. Yeah, and people respect that. They're like, ‘Wow, you told that much story in these amount of minutes?’ Yeah, that's impressive.

Sadie: Yeah, I'm crying and I'm feeling all of these unexpected emotions. [laughs]

Charmaine: [laughs] Yeah, it was an advantageous script. I was like, ‘I'm gonna have so much time,’ but 10 minutes is not enough time. [laughs] It's a lot of story to get out in 10 minutes. That was one of my major learning things because I'm used to getting 60 minutes. My two pieces of advice would be writing your script is evolutionary, there's not a world that exists whereas a writer, and I really didn't know this, you will write what's on the page, and then by the time it gets to set and then editing, it's just an evolutionary process that it goes through - the director has it, it goes through a change on set, and then it goes through a change when you're editing and you're just trying to keep the core story. And so, it's just an ever-changing process. And then, for a writer, write the pieces you want to see, don't look at the commercial value. Write something that you're passionate about, and then people are going to gravitate towards it, regardless.