Leslye Headland knows first-hand just how significantly Hollywood has changed over the last two decades.
She first broke out as an indie filmmaker with a distinct voice, writing and directing an adaptation of her raucous play “Bachelorette” in 2012 and following that up with the R-rated Alison Brie/Jason Sudeikis rom-com “Sleeping With Other People” in 2015, both indies that found audiences at Sundance.
Then in 2019, at the height of studios’ spending bonanza on streaming, she co-created the twisty, dark comedy Netflix series “Russian Doll” with Natasha Lyonne and Amy Poehler, directing half the season and picking up Emmy nominations.
And then, she made a “Star Wars” show.
“I think we’re in a really interesting in-between place right now,” Headland told TheWrap of the current marketplace as she continues to develop and produce projects through her Shoot to Midnight banner.
The company’s ethos was initially built on elevating “unacknowledged or underrepresented voices in dark comedy,” but as the market got more challenging after COVID, Shoot to Midnight “became about crafting relationships and seeking out female writers, specifically television writers, who wanted to get in and sort of break into this industry.”
That’s been a challenge recently, Headland said, acknowledging the rollback in DEI and female-led projects at major studios.
“That’s the type of development project that I think people are a bit more wary about than they were in the 2018-2019 era.”
Indeed, Headland’s original “Star Wars” series “The Acolyte” was caught in the crosshairs when it debuted in 2024, becoming the target of racist online attacks over the decision to center a Black female lead, played by Amandla Stenberg. The show was canceled after one season – a decision that didn’t catch Headland completely off guard, but still stung.
“I was not surprised by [the cancellation]. I think I was surprised at the swiftness of it and the publicness of it,” she said. “I was surprised by how it was handled. But once I was getting particular phone calls about the reaction and the criticism and the viewership, I felt like ‘OK, the writing’s on the wall for sure.’”
But Headland said she learned something vital through the “Acolyte” kerfuffle as she saw online creators — many of whom she’d followed for years before she made a “Star Wars” show of her own — rack up views (and thus ad revenue) for their lengthy reviews and recaps about the show. As she looks ahead, she thinks Hollywood is misunderstanding how, exactly, those models work.
“The content that is being put out by the streamers or the studios is being snatched up by these other creators, and so commentaries, synopses, live videos, all of the ways that these creators make money — through viewer-based ad revenues and their Patreons — there’s a lot of money to be made,” she said. “And by the way, have at it. Get your coin 100%. But it revealed to me that there is a misunderstanding between the studios and that engagement. They think of it as fandom, and in ways it is, but studios use it almost like this focus group.”
Ultimately, Headland thinks we could be moving towards a world where “the content being made about ‘Star Wars’ will be more culturally impactful than actual ‘Star Wars.’”
Read on for our full interview in the latest installment of TheWrap’s Office With a View.
When you first launched Shoot to Midnight, what was the ultimate goal in your head? Why did start your own production company?
The initial instinct was really simplistic, which is unacknowledged or underrepresented voices in dark comedy. It felt like “Russian Doll” was the first big Shoot to Midnight project that was not just something I had made, and so it felt like such a successful and fruitful collaboration that it became the blueprint for me in terms of what to look for moving forward when developing projects.
Shortly after “Russian Doll” in 2019-ish, right before COVID, I was lucky enough to sign an overall deal with 20th Television. I had a key hire, which was my former assistant, who then became creative executive and is now an EP of development and production. But because a lot of that overall deal was about me creating a “Star Wars” series, and that’s essentially all-encompassing, a lot of the development that we were seeking out and responded to were projects that I couldn’t come on to as a director. That was really interesting, because it started to become more about a producorial voice and less about a production company that was supporting simply what I was doing.
During COVID, there were a lot of projects that were picked up and greenlit into development, and it was very exciting, and we’d get to all of these great creative places, and then we found the market to be really difficult. With 20th, you essentially have two to three platforms to pitch to, which is a pretty narrow bullseye to hit. So COVID plus the strikes, the bullseye got smaller and smaller. Then it became about crafting relationships and seeking out female writers, specifically television writers, who wanted to get in and sort of break into this industry.
So we had the opportunity, during a very tough time, to continue to foster new talent, and specifically young women who didn’t have the tried and true go-to-market and everybody’s like, “Yes, absolutely!” It was much more of a, “Can you take a chance on somebody who has a great idea and a lot of talent?” That’s the type of development project that I think people are a bit more wary about than they were in the 2018-2019 era.
I bet there was a lot of whiplash too. “Russian Doll” is so great and unique, but does that even get made in 2025?
Oh no, not at all. I came in on a 20th Television property, a known IP, and I pitched that at the top of the year, and it was a great show, great concept, a lot of support internally for it, and I was very grateful for that. But it ended up going a different way and there wasn’t a pickup or greenlight to pilot, and it did feel like, “Gosh, a half-hour black comedy with a female lead who’s dealing with existential problems,” just that bread and butter that I developed both with my films and then also with “Russian Doll,” that’s a project that, at the height of streaming, would have sold immediately, especially if it had major talent attached to it or a big studio behind it.
What specifically is different about the market now?
It really does come down to not really a resistance to a pickup, as much as a resistance to engaging on development. I think that the streaming bubble is now bursting, and I think that started around COVID. It just started to feel like the amount of money that was going to have to be spent on eight to 10 episodes of television, that business model dwindled. It started to become something like well what are we pivoting to? There hasn’t been something that’s been ushered in to take its place. I think we’re in a very interesting in-between place right now.
So how do you forge ahead with Shoot to Midnight? Especially at a time when studios frankly are pulling back on female-led and diverse projects.
I completely agree. I did start to feel that when my “Star Wars” show came out. In 2024, I remember thinking, “Oh, gosh, I wish it wasn’t coming out in an election year.” I think that’s contributed to the move away from DEI hires, and I would say we are not a company that is interested myopically in that. As a queer woman, and my other hires are women, it just means that that’s my community. I am queer, so I just see the world through my specific lens and that means just doing different things.
There was a lot of unfair vitriol about “The Acolyte” online, and for it to be the first “Star Wars” show to be publicly canceled – Lucasfilm had never done that.
Really the whole thing with “The Acolyte” was always a major risk. It was a new part of the timeline. It was all new characters. It was a part of the lore where you couldn’t use a Storm Trooper, you didn’t have the reference of the politics and war that Tony Gilroy has brilliantly exploited in such a genius way in “Andor.” But all that iconography and all those visual references are original trilogy references, and our references were the High Republic novels and the publishing initiative and then the prequels, specifically with the lightsabers.
I also think that any gripes creatively with the show are completely valid. That’s people’s reaction. It’s usually their reaction to their own reaction. But like I said the show was always a risk. It’s the old adage of the first one through the wall is the bloodiest. And this is very similar to coming back to your question about the company, it was just very much, “Let’s shoot for the sky.” Let’s just go for it. So I have no regrets, and I’m absolutely obsessed with “Star Wars.” I still am, and I love my show, and I know that it was wonderful. And honestly, the designers that worked on the show are more responsible for it — because of what “Star Wars” is, creating that world is honestly harder than creating the narrative and the dialogue and the characters, that stuff I’ve done. It’s more hiring the right people, and all of those people were brilliant.
What was the experience for you to see the show not only get attacked but weaponized by certain parts of the media?
I have thoughts about this, and I don’t want to go on a tangent, so I’ll stick to the personal rather than the professional. I was not online. However, I am a “Star Wars” fan, which means I have always been, since the launch of YouTube, part of the “Star Wars” recap/criticism/lionization fandom community. These guys I’ve known for years and years. So when I got the information from others about what the weather report was, there was this real concern from friends of mine or co-workers of mine that saddened me. I also was like, “I know who these guys are.” You don’t have to tell me who’s talking about it or how bad it is online, I know exactly who they are. I supported them on Patreon. There are some of them that I respect, and there are some of them that I think are absolutely snake oil salesmen, just opportunists. Then, of course, there are the fascists and racists. So it runs a gamut. It isn’t just one thing or the other. So I think that if you’re in part of the fandom, you understand the genre and the tone of particular channels and creators. So in some ways I wasn’t surprised, and then in other ways I was disappointed. I think you always do that when you create something, it’s just that “Star Wars” is on a massive level of visibility.
The content that is being put out by the streamers or the studios is being snatched up by these other creators, and so commentaries, synopses, live videos, all of the ways that these creators make money — through viewer-based ad revenues and their Patreons — there’s a lot of money to be made. And by the way, have at it. Get your coin 100%. But it revealed to me that there is a misunderstanding between the studios and that engagement. They think of it as fandom, and in ways it is, but studios use it almost like a focus group. It made me start to think, rather than these fans are toxic, or this thing is being mean to me, it made me think more that the content being made about “Star Wars” will ultimately be more culturally impactful than actual “Star Wars.” I believe we’re headed into that space. Those IPs will continue to make money, but I don’t know how much they will affect the next generation as much as the content that is being created around those events, IP films and television shows.
That is a proper business model rather than a bunch of mean people. It’s a lot more financial than I think people realize, and as somebody that really has supported a lot of those channels financially and with my eyeballs, some of that stuff is probably the only content that a younger generation is seeing.
Was the cancellation decision shocking to you? Did they explain why? Was it viewership or creative?
It was kind of both. I was not surprised by it. I think I was surprised at the swiftness of it and the publicness of it. I was surprised by how it was handled. But once I was getting particular phone calls about the reaction and the criticism and the viewership, I felt like “OK, the writing’s on the wall for sure.” The viewership was a little muddled for me, because — and this is my understanding — with “Star Wars,” you’re not just measured within the marketplace that you happen to be in at that time, you’re measured against every other “Star Wars” show. We hit the Nielsens a couple times, not every week or anything like that, but a couple times it poked through. I feel like for a launch of a first season show that was trying different things, I think it could have been worth it to allow the audience it was meant for to find it. But that wasn’t up to me. So I fully respect the decision, even if I’m sad about it.
Had you plotted much ahead in terms of Season 2?
My showrunner and I had a lot of ideas going into Season 1, so we definitely were thinking about that, specifically with Manny Jacinto’s character. We always knew that Lee-jung Jae was going to be the emotional anchor of the first season, watching the deterioration of that father figure. So we had already thought ahead and thought about what type of relationship we wanted to look at in the second season. We had talked about all of that from a thematic and character standpoint, but in terms of actual narrative, there were only a couple sign posts that we knew we wanted to hit.
What’s next for Shoot to Midnight, and how are you applying these thoughts about Hollywood’s inflection point with the creator economy?
I’m coming out of “Star Wars” which was several years well spent, but coming up on the challenge of selling shows to streamers or to network and realizing what that that landscape is, I have been starting to reach out to different types of financiers, different types of platforms, and just getting a sense of what does it look like? What does that transition look like? Is there a prestige element to it that is interesting to particular people? A lot of the sites that I’ve thought about would be like Mubi. I’m definitely starting to try to figure out for me and for my company what that would actually mean and look like? We may just not be there yet.
What are you directing next?
I have two things that I’m circling. One of them is under wraps, and the other one is an adaptation of my play that was on Broadway about a year ago, “Cult of Love.” But I’m essentially pivoting to features just for the moment, because I am curious what that experience is like versus trying to develop TV and streaming. I’m gonna play around over there for a moment.
This interview has been edited and condensed for length and clarity.