Inside Rachel Bloom’s Showtime Pilot ‘Crazy Ex-Girlfriend’

Rachel Bloom made her first big splash in 2010 with the hilarious short “Fuck Me Ray Bradbury,” which was so successful that Rachel had the honor of being present for Bradbury’s first time watching it. Since then, she’s produced numerous other successful and equally hysterical shorts, released two albums (Please Love Me and Suck It, Christmas!!! A Chanukah Album), produced a short Disney musical parody, and written for and voiced characters on Robot Chicken.

Bloom, together with Aline Brosh McKenna, is now developing a musical television series for Showtime, Crazy Ex-Girlfriend. The show will follow Rebecca (played by Bloom), who leaves her job in a prestigious New York law firm in pursuit of love in West Covina, California.

Bloom and I recently had a chance to chat about how her experience in sketch, writing, and musical productions has helped prepare her for this opportunity.

So, prior to this, you produced a great selection of shorter clips and wrote for Robot Chicken. Has that made this a more difficult transition for you, since now you’re writing for a longer format?

No, no they helped me! I co-wrote it with someone who’s very experienced in a longer genre and also live-action. My foundation was in half-hour TV writings; Robot Chicken was sketch, but it wasn’t that different, because it’s a musical show and I’ve been doing musical stuff for a long time. I’ve been thinking about a show like this for a long time. Fortunately it felt like a very smooth transition.

Did you have anything in mind that you wanted to map onto when you were coming up with the idea for the show or was it something that just kind of came from you organically?

No, actually it came from the woman I wrote with, Aline [Brosh McKenna]. She reached out to me because she had seen one of my videos featured on Jezebel. So she saw all my videos and she set up a meeting with me and was like, “I want to do a musical television show with you.” I was like, “Oh, awesome.” She had wanted to write a movie called Crazy Ex-Girlfriend and because I have a couple music videos in which I play kind of a crazy girlfriend, she thought, “Oh maybe I can do a musical television show with you.” So it ended up working out really well.

How long has this been in progress?

We first met about it in May of last year, and then we spent a couple months just developing the show together. We didn’t write the script until we had a very elaborate pitch. So we first met in May of last year, we pitched it in late September of last year, and then wrote the script December through March, with like first rewrite, second rewrite, stuff like that.

I’ve read that Marc Webb is going to be directing; how did that come together?

We were looking for a director who was interested in a show like this, especially one who has musical experience and musical enthusiasm. Someone at Showtime knew that this would be right up Marc Webb’s alley, naturally since he directed 500 Days of Summer, and we sent him the script. He’s a big deal so I was like, “Ah, whatever happens…” But then we heard that Marc really loved it and wants to do it. He’s a fantastic person. He’s just been awesome to work with.

How will it be structured?

It’s basically like an actual stage musical where most of the scenes are spoken and take place in reality and then we go into the character’s fantasy for the musical numbers which are about three minutes, so they’re sizable musical numbers. There are 3 in the pilot. There’s a big song, a musical theater song, a pop song, and reprise of the musical theater song. It’s structured like a Broadway musical.

So you’re coming from Adult Swim and Cartoon Network and you’re moving into Showtime – what’s that shift been like?

I think the biggest difference between the two jobs isn’t just the network. Robot Chicken was a sketch comedy show which doesn’t have a plot. And this is a half-hour narrative, so it’s kind of like apples and oranges. I love writing and so the musical numbers just felt like along the lines of what I’ve been doing with my music videos. It’s very in my wheelhouse. So there are some things I learned from working with Aline about getting more in depth with the characters. I think had I thought about it when working in animation, but there’s certain… The way that she writes super in depth characters – what are there parents like, what were their childhoods like – it’s a way that I hadn’t thought. So it’s really going deep into character mode and going super deep in ways I never thought.

Has it been hard to think about your characters in deeper ways?

No. She’s just great to work with so collaboration’s been great. I don’t think it’s hard, it’s been really interesting. I’m just learning a lot and working a lot and collaborating with her in general. I’m learning a lot, there are difficult parts in changing stuff around. This went through several iterations which is really difficult in the way that writing kind of goes, but it’s been a really interesting process.

How have you two gone about writing the pilot?

She and I just get together and talk. We structure it like you’d structure writing any episode of television. We have a system where we outline it together, we talk through each and every scene in depth in the outline, and when we go to write it, we really just kind of riff on the scenes aloud and we do it aloud together. So it’s really fun.

Have you workshopped any of the show at UCB?

No, it’s been pretty separate. I mean, obviously the UCB training and their style of sketch writing is probably the biggest influence on my writing in general, learning the term “game” and writing sketches with “game.” I consider my songs to be musical sketches, and that’s the way I’m approaching songs in Crazy Ex-Girlfriend. And Aline isn’t UCB trained, when we’re writing the scenes, essentially we’re finding the game of the game. Every scene kind of has this “mini game,” as in any good comedy you’re either uniting a premise or uniting a pattern. But it’s been pretty much just working with her, but UCB in general is a huge influence that informs my writing.

So what stage are you in now?

We’re casting it. It’s great seeing all these amazing actors read our words in different ways, how they interpret the jokes that we’ve written and really, for each joke, going over the lines and thinking how each scene can be better. I think that’s been really gratifying, just seeing it come to life with actors reading it.

Do you have anything else in your mind that you hope will develop out of this, or has this been your focus since September?

Well I think this is an end-goal type of thing, where a musical television show for Showtime is pretty much the thing that I’ve been wanting. So obviously I’m making a lot of new relationships out of it as a fairly young comedian so there are relationships, but this is definitely an end-goal dream type scenario.

Phil Stamato lives and writes in New York, where he may also be seen standing up and telling jokes.

Inside Rachel Bloom’s Showtime Pilot ‘Crazy […]