You never know what a little procrastination can lead to.

Screenwriter Aline Brosh McKenna (The Devil Wears Prada, 27 Dresses) was taking a break from her latest film project when she stumbled across an animated Disney parody on YouTube. The woman behind it was Rachel Bloom, and after bingeing on every Bloom video she could find, Brosh McKenna knew she wanted to work with her.

Aline Brosh McKenna

Fast-forward a few years and the result of that collaboration, Crazy Ex-Girlfriend, will be entering its fourth and final season this fall. A comedy/musical series that stars Bloom in the title role, the show is about a young woman who leaves her career and life in New York City to follow “the love of her life” to West Covina, California. It also marks Brosh McKenna’s first turn at TV showrunner, but the experience was so positive that it certainly won’t be her last.

Creative Screenwriting recently spoke with Brosh McKenna about the genesis of Crazy Ex, her adjustment to showrunner, and the long-lasting professional relationships that have stemmed from this project.

Tell me about discovering Rachel on YouTube – what was it that stood out to you about her? What made you want to be involved with the series to the degree that you are?

The first thing I was attracted to in Rachel’s work was the writing – that’s what jumped out at me. The first video I saw was the Disney princess parody. I don’t know what screenplay I was working on at the time, but I was literally procrastinating in my office. I was on Jezebel, linked to the article and watched it. Rachel’s not in it – because it’s animated – so I didn’t realize that she was also the voice singing the part. It seemed inconceivable that someone who wrote that could also sing that well!

So I watched that video and was bowled over by how funny the writing was. I went to watch her other videos, seeing her and what she was like as a performer. I researched her career a bit and spent a good part of an hour watching as many of her videos as I could find.

I had had something of a standing offer from CBS to do television for them – my best friend, Kate, is the Comedy Development VP there. Every year she’d ask me and every year I’d say no. But I’d also function as something of an unofficial talent scout for her if I found somebody that I thought was talented or interesting and was in a TV space.

In Rachel’s case, I liked her work so much that I decided to set up a meeting between Kate, her and I. I didn’t really have an agenda for it – I was just so tickled by her work and wanted to meet her. When she came to the meeting, she really presented not as an actor, but as a writer – she was wearing what a writer would wear to a writers’ room. As soon as we started talking, I felt this strong intellectual connection.

Another thing I had liked about her videos was how emotional they are – they’re funny but there’s always some kind of tragic emotional “thing” happening to the characters. They aren’t just sketches in my mind, but have this other emotional component to them. I had had an idea for a long time to do something called “Crazy Ex-Girlfriend”, because it’s a female stereotype that interesting to me and one that I’d written about before – the “Dragon Lady” in Devil Wears Prada and “The Doormat” in 27 Dresses, for instance. Those are the kinds of characters that I’m interested in.

So as I was talking to Rachel, it just sprang into my brain to pitch her that idea. As soon as I said it, she immediately latched onto it and we all started talking about the times we had been crazy exes and had crazy exes. After the meeting, we walked out to the CBS parking lot and just stood there and talked. I immediately wanted to get together again to see what we had and go on to pitch it.

I hadn’t done TV in a while and my feature career was really busy. So the process of becoming the showrunner was gradual. Rachel and I wrote the pilot together and it got ordered…and all along the way, I was trying to figure out how I was going to have a movie career and continue to write features while working on the show. It was a process for me of thinking about whether it was something I wanted to work on full-time. By the time we’d finished the pilot, I was all in. We were expecting an order because Showtime had been so positive through the whole process – we really thought it was going to be a Showtime series and I had already been preparing myself for that.

But then they passed and there was a period of limbo where I was writing a draft of Cruella for Disney before we got this sudden CW pickup. I had watched Jane the Virgin and felt like it was a sort of spiritual sister to our show, especially since it has a strong, unusual female protagonist. Soit was a bit of a strange “Hail Mary” that the CW went for it. Rachel and I did a rewrite and it got picked up.

By that point, I was all in. I was still working on Cruella during the first part of the prep of Crazy Ex and not really understanding what it was going to mean to be the showrunner, be the head writer and produce the episodes. I did the best I could to finish up my screenplay obligations and then I was in full-time.

What is it like to pitch a “musical with dirty songs”?

We didn’t really stress the songs because we didn’t write them until we were writing the series. It’s always been about the story and the arc of the characters. It’s a pretty heavily thematic show, especially in the first season. So that’s what we pitched. The sales tool was the songs from Rachel’s videos. In my preliminary email to people, I sent three videos – but much to my surprise, most people had not watched the videos before they met with us. I realized after the first meeting that people were not going to watch it unless they were a little bit interested.

So we shifted a bit and the first thing I would do as a pitch would be to describe the videos and Rachel’s work. Then we would launch into it the same way you would pitch any other series – and we pitched all four chapters of the story as we saw it.

It was a pretty complete pitch but it focused on thematics, character, relatability and so on. And I think if you saw the videos, you could kind of see how we were going to use the music.

The series was designed to be four seasons – is it a blessing or a curse to have a predetermined number of episodes? Was there any flexibility to that decision?

As a screenwriter, I would never write a movie without knowing what the third act was. One of the reasons I had not done television was that, in the comedy space, television has for many years been made up of shows that spit out copies of themselves – there isn’t a lot of forward progression. Which I love! But I was more interested in telling a long-form story. Rachel was too, even though her background was more in sketches and animation. Her mind really went to the big picture – and still does.

We had this beginning, middle and an end, and it’s a rather slender premise. Basically, the way we saw it was as a rotating Rubik’s Cube – the different modalities of being a crazy ex. I think it’s something where if you vamped on the concept for a long time, it would become very tedious because it’s about a person’s progression through this phase of her life. These romantic obsessions have a shape to them, almost a narrative shape. That really is what the series is – the highs and lows of when you’re obsessed with somebody. Obviously, it’s heightened because her character has a mental illness; but essentially it’s about the progression of a romantic obsession.

I think we had in our minds four seasons of 12 episodes each, and we will end up having done more than we intended. But because it’s on the CW, it’s a little bit more of an ensemble piece than it would have been on Showtime. With Showtime, it would have been focused on just Rebecca’s character. So we’ve been able to find more stories because of that ensemble.

Tell me about the Crazy Ex-Girlfriend writers’ room.

It’s pretty glorious. Rachel and I wrote the first episode and two other sample episodes for Showtime on our own. Getting picked up so late meant we had to scramble to put our writers’ room together. Rachel had to go to New York quickly and we both read tons of submissions. The woman who was my assistant – and is now one of our writers and a co-producer on the show – also read a bunch of samples. We had about 10-12 people whose samples we liked and I met with them and reported to Rachel.

I had never staffed a writers’ room before and pretty much went on instinct. I would say that even though I didn’t have experience putting together a writers’ room, I have been in the business a long time and have met a lot of people. I had questions to ask that were, to my mind, very illuminating. We ended up with a staff of 10 people, plus Rachel’s husband and writing partner who had been on ‘How I Met Your Mother’ for five years – they were consultants the first three seasons.

We have a pretty big room! It’s completely intact – we have exactly the same people (except for one writer who left this year), and we’ve promoted two others. We’re a very cohesive group, and what’s great about it is that it’s a room that has incredible institutional memory. Everybody who’s there has been there since the first minute, so we have an incredible fossil record of what’s happened on the show. Everyone in there has tracked all of the progression of the characters.

In my mind, it’s an all-star room – everybody there has different and complementary strengths. Rachel is in the room for the first eight weeks or so and then is on set for the rest of the writing period. So I really rely on the writers’ room tremendously to get the script out, and it became obvious that it was going to be my responsibility to get the stories broken, outlined, written and out the door. As the showrunner, I supervise all of the elements – but the writers’ room is the engine room of the show. The scripts are the heart of the show and the architecture on which the rest of it is built. One of my jobs is to loop Rachel in over the course of the season so that she can give feedback on all of the scripts. She and I connect during the day or at night or on the weekend so that she is fully co-creating with me.

It’s an intense feat when you’re also in production. I went from writing a couple of screenplays a year – so a few hundred pages a year – to getting 900 pages out the door my first season. That was a transition.

I would say the next thing that most resembles writing is the editing process. Being in charge of the edit has been one of the joys of this experience. Having the ability to determine the finished product is an opportunity that a screenwriter never gets – you don’t get anything close to that. I see the editorial staff as an extension of the writers’ room, in some respects.

Do you work on the song lyrics as well or is that solely Rachel?

There’s a parallel writers’ room to the scriptwriters’ room, and that’s the songwriters’ room. That’s Rachel, Jack Dolgen, and Adam Schlesinger – the three songwriters we start with at the beginning of the year. I supervise that process and sometimes break ties. I’ve often come up with ideas for songs and a few lyrics, but I wouldn’t call myself a songwriter. What they do is another form of artistry, and they came together to write 115 original songs while we were creating all of this other content. Rachel stars in the show, Jack is one of our producers in the writers’ room and Adam produces all of the music. They all have full-time jobs on the show besides songwriting and still manage to write these songs. I’m tickled if I can make a contribution here and there, but they’re wizards.

This show has led to other projects for you. Can you tell me about what else you’re working on?

I did a pilot (Arranged) with Sono Patel, one of our writers, for Pop TV and we’re waiting to hear if that got picked up. It stars Moses Storm and Kiran Deol. We shot it during the hiatus and it was a great experience. I used some of the Crazy Ex crew, so that was fun.

I also co-wrote another show with Rene Gube, one of the other writers on our show. And I’m working on a script with two of the other writers – they are writing and I’m producing.

We spend a lot of time together and you start to kick around ideas – it’s been a natural outgrowth of the writers’ room. Rachel and I don’t have much time to work on anything at the moment, but I know we will in the future.

Tell me about Jane, your graphic novel. Is that a type of project you would take on again?

I would definitely do it again. It’s a very long process and it way pre-dated Crazy Ex. We waited a long time to get the artist I was in love with, Ramon Perez, who’s just incredible and so talented.

Looking back, I had come to a place in my screenwriting career where I really felt like I needed to be more in control of the material. Doing a book, a bit like doing a TV show was having final cut on the material. So in a funny way, the book is like an episode and I had the opportunity to collaborate with someone who’s absolutely brilliant. We were able to say, “The process is done when we’re done”. That was a great experience and it’s nice to do stuff outside of the regular Hollywood process – it’s definitely a purer process. Fifth-grade Aline thought she was going to write books, so it’s exciting to have one on my shelf.