“I Want to Play”: Talking with Sam Bailey


Sam Bailey is a writer and director from Chicago, currently residing in Los Angeles. She is the creator of the Gotham-nominated webseries You’re So Talented and the co-creator, along with Fatimah Asghar, of the Emmy-nominated webseries Brown Girls.

Bailey’s work has been reviewed and featured on many platforms including Elle, W Magazine, Fox News, and Out Magazine. She recently directed the Powderkeg digital series East of La Brea and has directed episodes of television including Grown-ish, Loosely Exactly Nicole, First Wives Club, and Dear White People. She is currently developing the film Sabrina with Bron Studios. Bailey is also the Digital Art Director of VAM STUDIO.

Recently, I spoke with Bailey about living in Los Angeles, missing Chicago, what stories she wants to be telling, and how directors actually get jobs.


The Rumpus: I am (without shame) very deeply Midwestern. And I never feel more so than when I’m working in California, especially when I have to be in LA. You’ve been out there full time for a while now, because that’s where the shows are. Have you adjusted? What do you miss most about Chicago? Isn’t it weird not being around friendly fat people? How can it feel like Christmas when there’s no snow on the ground?!

Sam Bailey: It took, and—if I’m being honest—is still taking, some time to get adjusted to LA. I think a lot of my hesitancy and inability to settle and breathe in this place is because the majority of my interactions in the city operate under the banner of Hollywood. And Hollywood isn’t exactly the place you go to seek stability, right? My first year in LA was interrupted a bunch with all the travel we did for Brown Girls so there was rarely any time (or money) to go explore the city, or the state, really, that entire time. Last year, I just worked a lot and when I wasn’t, I tried to be back in Chicago as much as possible.

What do I miss about Chicago? The community. I grew up in Logan Square with a bunch of play aunties who also grew up down the block from my mother in the same neighborhood. I’ve always been around chosen family and I think Chicago holds so much of that for me. And then when you break it down into these little subgroups—the arts community, the live lit community, the theatre community, the film community, and so on—I just miss the familiarity. And I miss people not being super fancy. Everything has a level of blue-collar energy in it, even in the art spaces. What else do I miss? I miss eating meat and cheese and not questioning if it’s really meat and cheese. I miss my small but reliable rotation of fuckboys; I miss getting paid in drink tickets; I miss hearing people yelling or throwing up outside my window. But, I say all this knowing that my body can’t keep resisting LA right now. I’ve got a good set up and I’m trying to lean into that shit. So I’ve recently purchased silk bed sheets and redecorated my bedroom.

Rumpus: Walk me through a typical California day: I wake up at ___, then I ___ while vaping legal weed, I buy a $12 green juice at ___ on my way to [insert fad exercise class] at ___, etc. etc.

Bailey: HA. Okay, so I wake up between 6 a.m. and 8 a.m. I’ve always been an annoyingly early riser so if I’m waking up at 8 a.m. it’s probably because I’m on my period. I wake up, shower, and listen to my morning playlist of Jamila Woods, Ari Lennox, and Tierra Whack while probably smoking a joint. And I’ll probably have a morning cig. I’m one of those trash people who still smoke every once in a while and in Chicago that was a badge of honor but out here there’s just a lot of judgement. But life is really stressful and I’m on my own porch and I don’t do coke so, please, let me have this.

And then I either go to a spin class or I’m going to some meeting in the city. In Hollywood they make you go on these weird date/meetings called Generals where you’re literally not sure if you’re being set up on a date or if it’s a meeting about possible work that will lead to you getting paid. I’ve gotten pretty good at them though. The questions almost never change and I don’t think they’re used to talking to people who haven’t been coached so they’re always surprised when I say something honest. You had this same experience, didn’t you? It’s so weird.

I had a guy ask me what’s the worst thing that ever happened to me in my life in front of a room of producers and writers who had just met me and I was like, “I dunno, my mom’s dead… is that what you mean?”

Then I come home, smoke another joint, probably read a script or work on a treatment or a visual deck or watch something. It is a blessing and a curse to get to a place where you get paid off of your ideas. Fifty percent of the time I’m like: “I have no more ideas! What do you want from me?!” And then I watch Project Runway and cry. Some nights I go to fancy parties… but I’ve decided to stop doing that because I just end up awkwardly drinking in a corner somewhere and crying in my Lyft home.

Rumpus: One of the things I want to know that I feel like everyone is too cool and/or polite to ask in an interview like this is, how do you get jobs as a director? Is there an agent who submits you for things or do you just sit back and wait for offers to pour in? Or do you hear about projects through various super-secret grapevines and pursue them yourself?

Bailey: I’m so glad you asked this! Because I think we need to be more transparent about the inner workings of this industry so, if you didn’t grow up in the business, you’re not completely blind walking into it (like I was). So, the answer is kind of all three, really. Sometimes—probably most of the time—shows and showrunners know who they want to direct their episodes, especially ones that are further along in seasons. If there is an open directing position, the network or producers might send those to agents and ask for a list. If they like your work or someone says something good about you, you go in and meet with them. And then it’s that weird, “is this a date or a meeting?” type thing and then if they really like you, you meet with the network and then if they really like you, you get the gig.

Now, sometimes, because I have a lot of friends who write on different TV shows, I’ll try to highlight those shows as places I want to work because I want to work with my friends all the time. For the most part, unless I’m going back to a show I’ve already worked on, I still have to meet and pitch myself and all that jazz. I’m not great at pitching myself. I have to get better. But I don’t get stressed on set, which they’re always surprised by, so I try to lead with that.

Rumpus: What are you working on now? Is there anything already out there that you’re dying to work on?

Bailey: I recently directed an episode of Dear White People that I’m incredibly proud of. Episodic directing is not always the creative gold mine you think it would be but DWP was different. Justin picks directors he trusts and that’s really lovely to experience. Right now I’m trying to focus more on directing features. I’m developing two features right now that I’m attached to direct. I’m also focusing more on creating my own content. I love bringing people’s visions to life but I feel like I’m doing myself a disservice if I don’t put that same energy into my own work. In terms of anything out there I’m dying to work on…? I don’t know. I really love the X-Men (even when the movies go off the rails). I grew up watching the 90s cartoons and then read the comics. I just really love the characters and the themes of acceptance and otherness. I’m a sucker for a good ensemble with sci-fi elements. I mean, I just think there’s so much there that still needs to be unpacked and I’d love to see a black woman take on that world and really give Storm the treatment she deserves. My personal motivation is always to protect Storm at all costs.

Rumpus: Both of your web series, Brown Girls and You’re So Talented, had a profound effect on me. They’re both so beautifully done, so human, so relatable. It’s like a miracle to sit and watch a thing your friend made and see that it’s a real thing that’s good, you know? I am phrasing that in the worst way because I’m dumb and ineloquent, but it’s like the feeling people expressed when my book came out and it wasn’t just a bunch of photocopied sheets of notebook paper I had stapled together. I watched You’re So Talented and was like “HOLY SHIT THIS LOOKS LIKE REAL TV.” Anyway, what are your passion projects these days? What are you just dying to make, for yourself?

Bailey: Wow, that really means a lot to me. I don’t think people know that I started writing essays and doing the live lit circle because I was trying to get good enough where I could possibly meet you. I just thought your work was so fucking spot-on and a voice that I recognized, but had never heard before, blah blah blah. I’m definitely a fangirl. My passion projects are a little all over the place right now. I got caught up when I moved out to LA and started wanting things I don’t think, deep down, I really wanted.

Early this year, when I turned thirty, I kinda just woke up and was like, “girl, you gotta change this course.” There’s a world where I could continue being a director for hire, like, there’s a clear trajectory for that. And that would be a fine and decent life for a lot of people and I think that’s great. But I don’t want that. That’s not my personal idea of success. It wouldn’t be a fulfilling life for me. What I’m dying to make is my own work. And to collaborate with the artists I want to collaborate with. I know too many dope writers, actors, directors, stylists, and producers to not be working with them constantly and on a level that pays us all for our hard work. So I’m focusing on a series I’m creating that’s an anti-romantic romantic comedy with lots of sex and snow because I miss Chicago and sex. In general, I just want to explore the vulnerability within black women in many types of genres and mediums. This year is about honoring the commitments I already have and also clearing everything else out so I can zero in on imagining those stories and how I want to tell them.

Rumpus: This is a purely selfish question: Are you ever going to write and/or perform more personal essays?

Bailey: YES. With all the gusto. Making TV and movies takes too damn long for me. I can’t have my ability to work be based on anyone else other than me. I just recently started getting back to writing personal essays. Right before things took off with You’re So Talented, I was pretty sure I was going to Prague to do this writing intensive and I thought that the web series would just be a way of showcasing my personal essays through a different medium. But everything changed for me after it dropped. I started getting attention and support as a filmmaker so that’s where my focus went.

It feels like a lifetime ago that we were in shitty dive bars reading essays for sport in Chicago, but that was like only four or five years ago! It feels like forever ago. But I really miss that brief point in my life. It was this experimental place that was such a departure from my training as an actor and feels completely different from my work as a filmmaker. But I do think they all influence each other in certain ways. I think a part of me is dying in LA because I haven’t been feeding some artistic mini-monster in me so… I’m getting back to it. Hoping to have something together by the end of the year. We shall see.

Rumpus: It feels kinda tired to ask you about ~being a woman director in Hollywood~ because we know! It sucks! So I won’t do that. Instead, I’ll ask: As a black woman director, how many people have you had to murder to get jobs? Because, seriously, it’s just you, Ava, and a handful of other women, right? How have you found community among your peers?

Bailey: I’ve only had to murder two male directors to get my gigs, but the way these guys act on set you’d think I’ve killed a lot more. They do not know what to do with me. They’re like, “Are you my daughter? Do I wanna fuck you? Do you know what a camera is? Are you a background actor?”I honestly wish I was exaggerating but… I’m only being slightly hyperbolic. It’s pretty bad.

Luckily, there’s a really dope class of black female directors coming up right now like Numa Perrier, Dime Davis, Nia DaCosta, Janicza Bravo—and a bunch more—who are doing great work with really distinct voices. I feel like it’s nothing but love there. A win for one of us is a win for all of us. I’m excited to support their work. But other than mutual social media love, I don’t think directors hang out with other directors a lot. It’s kinda this solitary thing, especially in the episodic world. I think. Or else I’m not getting invited to a lot of things…

Rumpus: Let’s talk about the future. I would like to work on a couple shows and then immediately retire, because this business is terrifying. What do you want your directing career to look like? Where do you want to go? What do you want to do?

Bailey: I want my directing career to be intentional. I want to make sure that when I’m directing, I’m only working on projects that feel like only I can direct them. That means I can’t attach myself to everything. I’m not that kind of director, who just loves directing for the sake of directing. I really have to love and believe in what I’m doing to be able to tap into what makes me a good director. Doing things solely for a paycheck is not sustainable for me (and I don’t knock a hustle, I’m just saying that can’t be my long game). It’s a fight I’m not willing to be part of for the rest of my career.

I want my directing career to be intentional and for it to leave space for me to work in other ways, as a writer, producer… maybe even acting again. I want to play. I want to be able to explore the human condition for as long as I get to tell stories. Wow, that is such a fucking privilege. Is that bad to want? The world is ending and I want to play. Ugh. Well… that’s all I got right now.


Featured photograph of Sam Bailey by Alexus McLane. Second photograph courtesy of Coakley Public Relations.

samantha irby writes a blog called bitchesgottaeat.com. More from this author →