It started with a song. Tucked in The Dirtbomb’s Dangerous Magical Noise, “I’m Through With White Girls” struck screenwriter Courtney Lilly, and before he knew anything about his characters, he’d nailed down the dilemma for his debut feature script. Since drafting and revising nearly seven years ago now, Lilly has watched the slow march of I’m Through With White Girls, or The Inevitable Undoing of Jay Brooks bypass the many challenges inherent in producing a feature film. It’s certainly a far cry from the instant gratification he normally experiences with television writing.

In 2000, in a break away from life as a daily reporter in Rhode Island, Lilly traded journalism for television, and by turns of hard work and fortune landed Nickelodeon’s Animation Writing Fellowship. Since then, he’s gone on to write for Invader ZIM, Arrested Development, Everybody Hates Chris and now currently works on TBS’ My Boys. In downtime after wrapping the season for My Boys, Lilly talks about niche comedy, the discipline, or rather lack thereof, in his writing schedule and the reasons he’s surprised anyone would want to ask him a question.

SM: I was hoping you could talk about the modern landscape of comedy. Do you see trends in romantic-comedy or just comedy in general?

CL: If you watch what’s on the Internet, you get a sense of the sensibility. More often than not, it’s just people not being able to act, or you see stand-up comics and what they do…That’s a far better gage of what’s actually happening than watching Saturday Night Live or watching a bunch of movies. The movies right now are just so watered down and so by committee that it’s hard to get something that shows an individual point-of-view or voice. 

The nice thing, at least about what’s happening in television, even though television comedy is in its nadir now, and there’s all this chaos, is that through this process of “We’re just going to throw things up and see what sticks,” you’re going to see more interesting creator-driven comedy.

As far as comedy is concerned, all audiences are fragmenting. Comedy relies on A: Everyone being able to get the joke. As the audience fragments, and as people get their own individual interests, the thing that’s hurt comedy overall is this idea that kids who are big into skateboarding aren’t going to get a comedy about basketball; people who are in their 40s aren’t going to care about a comedy about kids in their 20s who are into computers. As we all get our specific interests, that’s going to break down to where comedy breaks down by those interests. That’s probably happening and probably will continue to happen because comedy’s not funny unless you get the joke. Comedy’s not funny in other languages and other cultures more often than not.

If anything is going to happen, you’re going to see more of a niche, but then you never know. There are those (comedies) like Knocked Up that are so universal, so character driven that they become very successful. If you’re going to catch a big audience, that’s what you’re going to have to do.

SM: When you were working on (I’m Through With White Girls, or The Inevitable Undoing of Jay Brooks), how did you walk the line of trying to hit a niche while knowing at the same time that you had to have those universal elements?

CL: It’s pretty much a straight romantic-comedy story. Guy finds the girl. Guy gets the girl. Guy loses the girl and then tries to get the girl back. When you’re working with a genre, I think it’s real easy to stay universal. You’re pretty much just identifying and working with the characters and the situations…It wasn’t very hard structurally to come up with what to do because it would be wholly familiar to any audience what was going to happen.

The thing they say in romantic-comedies is: What keeps them apart? It’s flipped on its head slightly in this one because (Jay and Catherine) spend a good amount of the time together, and that is calling back to ripping off Annie Hall as much as possible—that movie’s brilliant. What’s going to keep them apart is internal and in his head.

I took a chance, and I felt that everyone would get it because it’s so familiar. Like a horror film with murder, blood, all that kind of stuff, with romantic-comedy everybody knows that there’s going to be a problem with the relationship, but they’ll work it out. 

SM: How did you go about crafting these characters? The one thing that has been so apparent not only when I was watching the film but also when I was talking to (Producer Lia Johnson and Director Jennifer Sharp) is that you’re trying to challenge a lot of perceptions.

CL: Character work is like anything else. You try to figure out what makes these people work, what qualities they have. It’s very typical romantic-comedy conceit that (the main character’s) afraid of commitment, but I thought that was the best way to go about it through this character. I wasn’t trying to challenge things as much as I was trying to represent something that was more honest to what I write, what I do.

SM: Unlike so many romantic-comedies, the comedy here is really subtle. I’d mentioned this to Jennifer. My favorite joke is the one about the title of the book The Inevitable Was Bound to Happen…So much of the humor is built on that witty repartee and also that subtle humor. How do you get in there and allow for those jokes to work without worrying that a mainstream audience might not pick up on all those subtleties?

CL: That goes back to some of my sensibilities. A lot of times (comedy writers) drive to hit a joke, and it’s like, “Alright, we get the joke. Where’s our laugh track? Where are we going?” Even while watching a movie, it feels like, “Oh, that’s the joke.” You either respond or you don’t respond. A movie like Annie Hall has plenty of jokes, things that just knock my socks off. So, a lot of it was just creating a world, a texture.

It’s funny you brought up The Inevitable Was Bound to Happen. Lia and I went back-and-forth about the title [of the film]. The title for me didn’t have to be I’m Through With White Girls. That’s just where the idea came from and was the original title of the script. She really loved The Inevitable Undoing of Jay Brooks. I never understood what that meant and what it said. It never said anything to me, particularly because the whole “inevitable” thing was a joke.

(A college friend) was writing an article about the Columbia University tennis team, and that was his lede. They just let that pass through for some reason. Nobody was paying any attention that it was as silly a lede as he could possibly come up with. It makes no sense. That’s always stuck with me. Little things like that you have to pepper in. In everybody’s real life, they have things that are almost like inside jokes, things that certain people find funny…Essentially comedy, in a lot of ways, is a volume business. The more you put in there, and the more subtle it is, you have a greater chance to get people to latch onto certain things.

The one joke that translates everywhere is somebody falling down. Slapstick. If you can find a world where you can pepper in all those different (elements), keep the story going and punctuate it with something that’s a little different and not necessarily germane to this type of story or world, it makes it all more interesting and draws people in.

SM: What was it like seeing the idea go from the script to the screen?

CL: The first real chance I had to see (the film) and feel, “Oh, this is kind of what I wrote, and this is what it is,” was at the Hollywood Black Film Festival, where we were in a theater with a bunch of people and we were watching it with an audience…Rarely do you get to watch comedies—specifically with television—rarely do you get to see them with an audience like that. Comedy is meant to be seen with an audience. Laughter is infectious, and when you see something like that and see the way people are reacting to it, it’s really the only way to read if this was successful. So, that was a really nice punctuation to the whole process.

SM: From a writing standpoint, where would you like to see the film go from here?

CL: Once (a film) is written you’ve got to let go of it in a way, especially in features where there are rewrites and casting, all these things that you have no control over. Until you get into the situation where you’re working on producing it, directing it yourself or doing all those other things, you let it go. For me, my final stage was seeing it at the Hollywood Black Film Festival and seeing it with that audience. From my end, I’m set and fulfilled by the whole experience. Just seeing it again, and going back to look at those first drafts I did—I did eight or nine drafts before Lia even saw it—it’s just good to go through and say, “Oh, that’s right. Don’t get discouraged when you write something that’s terrible. The ideas are there. Keep going over it and refining it.” There were a lot of positive aspects for me, and I hope for everyone involved…

SM: As a backtracking questions, with these eight or nine drafts you wrote before the script got to Lia, how did you go about writing them? How exactly do you write?

CL: In television, you’re working in a room of people most of the time, and so we’re all bouncing ideas off of each other. Then you go and come back in a week with a script. I need deadlines, and I will usually wait until the very end. I’ll write at the last minute. My old experience as a journalist really helped because all journalism is basically deadline writing. When I was at a daily paper, I’d have a couple of articles to write a day, and you’d have to get it in before your deadline. You’d be thinking about your article; you’d be writing it in your head before you even sit down at a computer, and that’s kind of what I do now. I’m not very good at planning ahead of time, being like, “Oh, well, I’ll get up, work from nine to noon, take an hour lunch, come back and I’ll work say four more hours and call it a day. I’ve got seven solid hours of work.” There are all kinds of difficult messes that people have done to get them to be more efficient, and I can’t do any of that. I have ideas. I know that I have time to do it, and I’m going, “Okay, I have to have this done by July 1.” Fortunately, I’ve been pretty good about gaging in my head how long it takes to get a first draft of something out, spit it out, get that done, let it sit for a little bit and then go back to it. It’s fit to start. That’s how I work. With the I’m Through With White Girls script, the first draft came out really quickly. I sent it out to different people to get notes back, and then I was just working on it a few hours a day as I needed to to get it to where I liked it. I wish I was more disciplined. I wish I was the kind of person who could spend time assigned to do all that, but sometimes I feel like reading a book, so I’ll read a book. Then at night I’ll work from two o’clock in the morning till six o’clock; I’ll sleep; I’ll wake up; I’ll work some more; then I’ll read a book or see a movie, whatever I can. I just don’t have that discipline, and it’s probably really valuable to have that discipline. I bet you’re much more prolific if you have that type of discipline.

SM: This is a question I ask everyone because I enjoy hearing the different answers. What is one question that you’ve always wanted to be asked about your writing but that you’ve never been asked?

CL: That’s a really hard question. Most of the writers that I know are particularly private people who express themselves, if they do at all, on the page. So the idea of somebody asking them a question and having to give a verbal answer—you’re taken aback by it. The fact that anyone’s ever asked me a question about anything I’ve ever written is odd to me in a way.

Honestly, I have absolutely no idea. Maybe, who are your influences? I could at least sound like I’ve read a lot.

I have no idea. The idea is weird to me that people ever want to ask writers questions. People ask writers questions all the time about, “How do you get this done? Where do you get things done? What is your inspiration?” One of my best friends just came out with a novel, and it debuted (June 26) even. I was reading an interview with him, and he was going through the same thing, trying to figure out the whole, “What do I say?” The reason why a lot of (writers) get things done is because they sit down and do it. That’s the hardest thing about writing: taking the time, carving it out, being by yourself unless you work with a partner and doing it. As much as anything, that’s what separates people from those who work more often. There are plenty of really, really dedicated people who unfortunately don’t have the talent, don’t see ideas clearly enough and can’t get over a certain hurdle, but more often than not—I know plenty of smart, talented people who just don’t have the temperament to just do it. Part of that temperament also is that you need to be able to spend time alone, to sit down, actually try to accomplish something, finish it, just be in it, meditate on it. It’s also the kind of attitude that makes it hard sometimes to imagine someone asking you a question.

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