In The To Do List, protagonist Brandy (Aubrey Plaza) attempts to cram an entire lifetime’s worth of sexual experience into a single summer before starting college. The film itself, however, took a much longer, more laborious path to maturation. Writer-director Maggie Carey wrote the script—originally titled The Hand Job—on spec while she was pregnant with her first child and recently unemployed. After getting passed over by several studios, the script appeared on 2009’s Black List, an annual survey of notable unproduced screenplays, thanks in part to the support of producer Jennifer Todd, who responded to the script’s female-centric take on the raunchy sex comedy. Following a 2010 staged reading at the Austin Film Festival—which featured Plaza, Carey’s friend from her time with Upright Citizens Brigade Theatre, and Carey’s husband, Bill Hader, both of whom ended up in the final film—Carey picked up enough momentum and financing to film The Hand Job over 24 days in summer 2011. After receiving a new name and changing release dates several times, The To Do List finally makes its way to theaters this month, nearly half a decade after it was written. 

Such tenacity from a first-time writer-director usually indicates a passion project, which The To Do List certainly qualifies as for Carey. A longtime improvisor with Upright Citizens Brigade and iO, Carey dabbled in web video and reality-TV production in the years leading up to the film, which is loosely inspired by her own experiences as an overachieving teen in Boise, Idaho, in the mid-1990s. On the day The To Do List opened, Carey spoke to The Dissolve about her path to comedy filmmaking, the incestuous comedy world that helped populate her cast, and keeping The To Do List’s nostalgia earnest instead of ironic.

The Dissolve: The conversation around The To Do List has been focused on the fact that it’s a female-created and fronted film, which is sadly unusual in cinema, but particularly in a sex comedy. What’s your reaction to that sort of narrative? Do you find it more restrictive or empowering?

Maggie Carey: Oh, empowering. I totally understand why that would be part of the conversation. I don’t know why it’s that way, because [women] did get the right to vote a long time ago. [Laughs.] So I’m not sure. But I would say I came from a really—in terms of comedy, I started at UCB Theatre in New York, and that was always a place that was never about male or female, it was just if you were funny. I think there’s something to be said that Amy Poehler was one of the founding members of the theater, and it had a lot of great, really funny female acting teachers, and then every night, you would go to shows and see really funny women on stage. And I was—until last week, because we moved—I was improvising every week, and half my team was always women. In a group of eight improvisers, there were always at least four women, so I think I was very lucky that in that time, I was never taught that. It was just, “Are you funny or not?”

The Dissolve: Before you got involved with UCB, you went to film school, right?

Carey: Yes! I went to University of Texas at Austin.

The Dissolve: Was comedy filmmaking always a goal?

Carey: Oh, absolutely. However, I grew up in Idaho, and you just don’t have a lot of access to a lot of comedy. [Laughs.] There’s a great stand-up place there, Funny Bone, but I didn’t know about it. I wasn’t exposed to it. And then I went to undergrad at University of Montana, where I played soccer and worked at the PBS station. That was how I learned to shoot and edit. I shot a ton of sports, and learned how to edit at Montana PBS, and actually did a documentary while I was there. Which, I absolutely love documentary, but I always wanted to do comedy. Even just being there was one step closer to equipment, and being able to learn the technical side of filmmaking.

So then with film school, Blair Witch Project had come out and Clerks—there was a loose association with someone from Clerks being from Boise, Idaho, and they went to film school in Vancouver. All of this might be myth, it might be wrong, but all of a sudden, it was like, “Oh, film school!” [Carey is most likely referring to cinematographer David Klein, who shot Clerks, Mallrats, and Chasing Amy. —ed.] Like, you have to go to film school. My improv troupe in Montana, we had gone to an improv festival in Austin, and they had a film school, and Austin had, and still has, a really good comedy scene in terms of stand-up and improv. It was a school I was really excited when I got accepted to. Plus, Austin has such strong examples of independent filmmakers, like Richard Linklater and Robert Rodriguez, and they’re just such a really cool, artistic community. And it’s a real do-it-yourself kind of town. Once I got there in school, everyone, whether they were in film school or not, was doing their own indie movie. So that was really fun. 

Slacker really put Austin on the map for indie film. That was such a fun place to be for film school. I had great, really cool classmates, because I was a grad student, but no one was doing comedy. So I would hang out with the undergrads who were doing comedy, and then they would crew all my stuff, and I would help with theirs, and even when I moved to L.A., I got my first job from undergrad students. [Laughs.] I was their T.A. with a Master’s degree, but they were the ones getting me my interview for my second-assistant editing position for this reality show. I’m eternally grateful for them. [Laughs.] 

The Dissolve: Was that around the time you started doing web video?

Carey: That came the year I moved to New York, because YouTube existed. I had done short films, but there wasn’t YouTube. We didn’t post them online. You had to get into film festivals. Then, if it got in, you had to tour the film festivals, and that was really expensive. You had to apply, which was always like, a $50 entry fee. It was really expensive. And then if you actually got in, you would have to pay your way to get there to see your film play in front of a crowd. My first web short was The Jeannie Tate Show, and we posted that only a couple months after the “Lazy Sunday” [Lonely Island video] went up. We even for a second were like, “Oh, should we post it online, or should we do film festivals?” And then it was like, “Thank God we put it on YouTube,” because we lucked out and got a bunch of hits. Aubrey was in that, and Liz Cackowski, I co-wrote it with. I directed, and Liz is the main actress. We got a ton of hits on YouTube, and that was how I got an agent and a manager, was off YouTube. I was also doing UCB at the time. So for comedy, I think YouTube was huge in getting exposure so I could move on to eventually doing the feature.

The Dissolve: In The To Do List, Aubrey Plaza’s character, Brandy, is pretty explicitly modeled on you as a teenager, minus the actual writing of a to-do list, correct?

Carey: I think a lot of her point of view comes from my point of view as a teenage girl.

The Dissolve: Did that have any effect on your direction of Aubrey Plaza’s performance?

Carey: Yeah, I made her have the same haircut that I had in the ’90s. No layers, a lot of split ends, and bangs. Very easy. Not a lot of maintenance. You cut your hair once every six months, and it’s usually done by your friend.

The Dissolve: I’m waiting for that to come back in style.

Carey: Yeah, I know. [Laughs.] We can blame Friends. I’m not kidding. They’re the ones who started layers.

The Dissolve: Aside from denying Brandy the ability to just Google what a pearl necklace is, did you set it in 1993 just because that was the year that was important to you?

Carey: Yes. You write what you know, and I definitely know the ’90s as a teenager. Absolutely, there’s no other reason than that. But I do think it’s interesting in terms of how technology has changed, how teenagers socialize. And it really is kind of crazy even in the last three years, since I’ve written the script, how much again, technology has changed with Twitter. It’s crazy. It’s so different. But it was important for me that it was early ’90s, before the Internet. It existed, but nowhere near how we use it now, and also before cell phones were readily available.

The Dissolve: With period-specific stuff, particularly this era of the early 1990s, references can often stand in for a joke. When you’re writing these things, how do you avoid falling back on, “Oh, ha ha, skorts. I remember skorts”?

Carey: I don’t think the references are in there as a joke. They’re in there because they were a specific thing, you know what I mean? It’s great that it plays as a joke, but there are tons of references that don’t get laughs. So I think you don’t write for the joke, you write for the reality.

The Dissolve: So it’s more about creating the setting?

Carey: Yeah. Like, Beaches is in there because it’s completely earnest, and coming from an honest place. My best friend, she called me and said, “My mom and my aunt just saw Beaches, and they said, ‘This is the movie every girl must see with their best friend,’ and if you see this with anyone else, we won’t be best friends anymore.” So of course I saw Beaches with her, and it still bonds us to this day. So it’s in there very earnestly. I think a lot of humor comes from an honest place. 

Same with the Ford Festiva. That’s the car that Johnny Simmons’ character, Cameron, has at the drive-thru when he gets really upset and tries to get out of the car, but the automatic seatbelt cuts him in the neck. That’s the car I had in high school! That’s why it’s in there! And then he as the actor, literally, was trying to get out of the car and he forgot about the automatic seatbelt, which we often did in high school, so that’s why it’s there. Also with the Hillary Clinton photo, the Clinton/Gore campaign was the first campaign I volunteered on, and that’s why the Pro-Choice Pro-Clinton shirt is in there, because as a teenage girl, I was wearing that T-shirt around Boise, Idaho, a very conservative town. So it’s there for a really earnest reason, and absolutely we should laugh at that. I think that’s okay, too. I really admired Hillary Rodham Clinton and what she was trying to do for universal health care when I was a teenage girl. [Laughs.] I really was into her, and saw her as this incredible role model, and it’s fantastic that now she’s the former Secretary of State, and hopefully our next president. And I’m not joking when I say that. [Laughs.]

The Dissolve: The budget for the film was around $1 million, right?

Carey: Mm-hmm. I think it was like $1.2, once we got the post and music.

The Dissolve: That’s incredibly low, considering the period aspect, and especially the music, which must have been expensive to license.

Carey: The crew was union, but it worked out a deal with the union called Tier Zero, so the crew basically worked for minimum wage, but they get their hours for their health benefits. It was a short shoot. We shot it in 24 days, so you can get people for that amount of time who don’t—they want to shoot in L.A. in the summer, they want to be home with their families, they don’t want to travel out of town, where a lot of movies are shooting. So we were lucky the crew would do that. And then the actors all worked for scale. And my music supervisor is fantastic, Howard Paar. He worked really hard. He’s British and started his career in the ‘90s, and so was actually legitimately friends with a lot of the managers. We had to screen the movie for almost every band, and he just insisted, he was like, “I know it’s not a lot of money, but will you please watch this movie?” Because he really believed in the movie, and he was also very great in his strategy where he said, “This isn’t something you can just pull a scene and show them. They need to watch the movie. They’ll get it. They’ll want to be a part of it.”

The Dissolve: Speaking of doing a lot with a little, the casting is impressive, given the sheer number of characters.

Carey: I know, and that’s the other thing I did not—as a first-time director, I didn’t realize how ambitious the script was for the budget we had. I think usually with this kind of budget, you’ll have one or two main characters and very few locations, and this was not the case. This is a big ensemble. The ensemble cast is the strength of the movie. So Aubrey and I met at class at UCB Theatre, and she acted in my web shorts, and I wrote the script with her in mind. And then Bill Hader had no choice but to be in the movie. And his character’s name is Willy, so that’s a big stretch. And then Jennifer Todd, my producer, she read the script as a spec, and after the studios passed, she was very committed to getting it done and getting it set up independently. So the four of us really just reached out to our friends who were also fans of their work.

The Dissolve: You’re a performer as well. Did you ever have the urge to sneak yourself in there?

Carey: Oh, no. When I first went to L.A., I so desperately wanted to work in film in any capacity. My résumé was the worst, because I was like, “I can write! I can direct! I can produce! I’ll be the A.D.!” It was literally, “I’ll do anything!” I realized I just needed to focus. So no, there was no thought of putting myself in the movie. I’m much more comfortable writing and directing. I like it. It’s hard. That’s enough.