Rachel Bloom and the Crazy Ex-Girlfriend Creative Team Break Down 5 of the Show’s Songs

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Photo-Illustration: Vulture/Getty Images

When the marketing for Crazy Ex-Girlfriend started rolling out last summer, some in Hollywood were ready to pounce. The billboards, planted all around Los Angeles, featured a pretty young lady with a manic look in her eyes, clutching a broken balloon string, with the caption “Never. Let. Go.” You could feel the Twitter outrage brewing: How dare a male-dominated corporate-broadcasting marketing team portray a young woman as being obsessed and crazy over a man!!!

But after seeing the gloriously silly opening credits, in which Rebecca Bunch (Rachel Bloom) sing-tells us why she moved to, of all places, West Covina, California, we knew we had something uniquely subversive and thoroughly empowering on our screens. Not only does Rebecca acknowledge society’s double standard for women who’ve been jilted (on the usage of the phrase “crazy ex-girlfriend," she says in the opener, “That’s a sexist term!”), she fully owns the ensuing, decadelong bout of depression and anxiety that follow in the wake of breaking up with her high-school summer-camp crush, Josh Chan (Vincent Rodriguez III). It’s for these reasons — and many others outlined here by critic Matt Zoller Seitz — that CW’s Crazy Ex-Girlfriend was named the best show on TV by Vulture.

Co-creator and star Bloom, with her writing and producing partner Aline Brosh McKenna and music supervisor Adam Schlesinger, joined Vulture's Stacey Wilson Hunt onstage in May at Vulture Fest to discuss how their failed Showtime pilot landed at CW, the show’s groundbreaking integration of musical numbers into the series’ narrative, and their distinctly different pop inspirations for five songs from the show — from Sondheim to Huey Lewis.

RACHEL BLOOM: My in-laws are here. Actually, half of Long Island is here.

ALINE BROSH MCKENNA: Maybe I should start by zipping my pants, which are totally unzipped.

BLOOM: Wait, you know that’s my new bit onstage, to check my fly because I always think my pussy’s out on stage.

HUNT: I think we got off topic, just a bit.

BLOOM: I don’t care. I have been doing press all week for Upfronts and been all on message. “Oh, so glad to be here ... ” I’m going to talk about my pussy.

HUNT: For that we are so grateful. Everyone okay with their flies?

BLOOM: Adam, you fine?

ADAM SCHLESINGER: I want to talk about my pussy!

HUNT: So, we are going to showcase five individual songs from the show, and do a deep dive into each one about the roots of their inspiration and how they came together. But first, for those who don’t know the story, tell me first you two met, which is a very interesting story, and how you came to take on this incredible show, which is renewed for season two.

MCKENNA: I was avoiding work one day, procrastinating, and I was on my computer and I saw a link to one of Rachel’s videos, and I was very smitten with it right away. And it was one that she actually she doesn’t appear in; she just wrote it and she sang it. It never occurred to me that the person who was singing was actually the writer. It didn’t compute. Then I watched a whole bunch of her videos; you can fall right into the Rachel Bloom [online rabbit hole]. That’s worth an hour of your life. Then I just wanted to meet her. I was very taken with her brain and the way she did those music videos and sort of the spirit of them. So I called my best friend, who works at CBS, and, she facilitated a meeting. And it really was the best blind date. I’ve never really had a successful blind date. And so we met and she walked in and I didn’t know if she was going to be like a Glamazon actress …

HUNT: Are you saying she’s not a Glamazon actress?

MCKENNA: She is a Glamazon. But she has many sides to her. And one of them is nerdy writer, which is what I am, too.

BLOOM: The [way] you always tell the story is that I showed up in a trash bag.

MCKENNA: I almost told the story that she was wearing cargo pants. But I stopped because Rachel doesn’t own cargo pants. But in my mind, that’s what she was wearing. So then I had this idea to do this thing called Crazy Ex-Girlfriend. While we were talking it struck me all of a sudden that this was the way to do it. That so many of the characters she does in her videos are crazy somethings. So we started talking about it in the meeting and then we walked outside to my car and continued talking. Rachel had never met me before and was not super familiar with my work.

BLOOM: I had seen The Devil Wears Prada!

MCKENNA: And I was like, we’re going to do this. We’re going to do a pitch. We decided we should go to cable because Rachel was not that well-known and we wanted her to be able to star in the show and we were afraid if it went to a regular network that they would replace her.

BLOOM: And the idea of having to audition for a show that I created. I had just done an audition for another thing, that a role was created for me, and this was the actor inside me, like: It’s mine to lose. Like if I don’t get this part, I fucked up and I’m not talented.

MCKENNA: Like, if we are going to create a musical television show about a mentally ill person, why are we? Why are we going to cast, like, Lea Michele in it? So we just took this idea and we, like, drove around in my car and we went to every network we could find. And we found a home with Showtime. And we made it with Showtime, but didn’t work out there. And wonder of wonder, miracle of miracles, God took us by the hand and we got to the CW. We actually met with Adam when we were thinking about doing it at Showtime, because Adam and I have known each other for a very long time. Adam is the only person to partner with us on this, and he was like,"Great, sounds great." And then there was a long period, it was about six months that went by between when we were passed on by Showtime and when we knew we had a show at CW.

HUNT: And during that time Jane the Virgin had become huge and therefore they were more open to new stars and these types of stories; female-centered one-hour comedy dramas, which is not an easy sell.

BLOOM: Actually, I just remembered something. Aline took me to the CAA Golden Globes party the year Gina had won. We were still in a good-ish place with Showtime and you turned to me and you were like, ‘This is going to be you next year, you’re going to win the Golden Globe next year.’ And then we got passed on. [Laughter.] The point is that we got passed but you said that to me and it felt, fucking beshert. I don’t know if that’s the right use of beshert. [Hebrew for “meant to be.”]

MCKENNA: We had a very dark period there because we’d made this pilot that people loved. I’m not generally very confident about stuff that I’ve made but we were really like, "This is it, people are going to like this." Then it started to go south very slowly. Spiraling.

HUNT: These stories help to inform the majority of incredible shows on television. Breaking Bad had a similar journey.

BLOOM: It’s very competitive. I also want to say, to even have been able to shoot a pilot … I’m an unknown, auditioning actor, working-ish TV writer. I got to write and star in a Showtime pilot? That alone was a huge career maker and so it’s not like oh, boo-hoo we had this dead pilot. But it was hard when you fully realize a vision and you think it’s over.

MCKENNA: But just to say that if you do something and you believe in it, you have to submit it to people to the point of being embarrassed. People kept coming up to Rachel and I being like, you know, you should really try Netflix. It was like, have you tried Hulu?

BLOOM: Amazon is doing some pretty nifty stuff!

MCKENNA: And it was like, yes, they passed. They passed.

BLOOM: Netflix passed. OB/GYN offices — they passed.

HUNT: Even with the UTI story line? [Laughs.] Well, now let's look at what they missed out on.

1. Settle For Me

HUNT: The first song we are going to dive into is one of my favorite songs. It for me recalls the great top-hat musicals of the '30s and '40s. It’s also the only song I know of that has a line like this: “If he’s your broken condom, I’m Plan B.” Classic. It’s Ginger Rogers and Fred Astaire. “Settle for Me.” And I want to just give us a little bit of a primer. This appears in episode four, sung by Greg. As Rebecca is starting to feel out her relationship with Greg, played by actor Santino Fontana. 

MCKENNA: One thing I want to say about the songs is that they are the egg, and the show is the chicken. We form the show and we figure out the story and the songs have to adhere. It doesn’t go the other way around, it rarely does. Once in a blue moon, a song is so funny that we insist on finding a spot for it. But most of the time the songs have to suit [the plot]. For this one, the particular character dynamic, this relationship between Greg and Rebecca, was shaped a little bit by the song, too.

BLOOM: This is the type of song I’ve been wanting to do for a while. I listened only to show tunes up until I was 20 years old.

MCKENNA: Oh, so yesterday.

BLOOM: Basically yesterday. I can tell you everything about [Stephen] Sondheim but I don’t know what the Rolling Stones are. I mean, I do, I do. [Laughter.] You know I come from alt-comedy and so, for a long time, I pitched two musical television shows that no one cared about before this and for a long time I wanted to do a number, a sort of classic Fred-and-Ginger number, but set in a modern setting with a modern twist. And I remember I had this idea for like a web series I wanted to do of, like, a Fred and Ginger number at a frat party where people would be dancing and then someone would throw up, but in the person’s mind it would become a fountain, you know? [Laughter.]

MCKENNA: We can still do that!

BLOOM: That might be a song now.

HUNT: Let’s go to the first song clip now, and then talk a little bit about it.

SCHLESINGER: What happens in a lot of cases in the show is that Rachel has an idea and maybe sings it into her phone or does it on the piano at her house; she had an alternate melody, and she already had the title for this song worked out.

BLOOM: I already had most of the lyrics.

SCHLESINGER: And she had most of the lyrics. And she sent me a demo that was a different melody. And I said I really love the idea for this song and I totally get it, it’s perfect conceptually. And I just had an idea for the melody that was a little bit jauntier than the one she sent me. The one she sent me was sort of like [sings sultrily].

BLOOM: Mine was a little more ‘40s or ’50s; yours is ‘30s Cole Porter.

SCHLESINGER: I’m a little older than you, so ... [Laughter.]

BLOOM: You and Cole were like roommates, right? [Laughter.] This was one of the first songs I’ve ever written for a guy. Because we had written songs for [co-stars] Donna [Lynne Champlin] and Gabrielle [Ruiz], I wanted to take the first pass at “Settle for Me” because it was so close to my heart; again this idea of doing a very musical-theater-feeling song with a very modern bite to it. What’s interesting to me about this song is that it’s an example of what’s interesting about the Greg/Rebecca relationship, which is it’s this constant struggle for power. He is debonair, very very masculine, but it’s a completely emasculating, embarrassing song. She has all the power even though she’s the one in the twirly gown, the girl being led around. That’s their relationship. He constantly thinks he’s better than she is, but at the same time he’s on a leash by his dick … and then later it switches, of course, when finally he plays hard to get … she really likes it later but he’s also really scared inside. It’s really fun to play — because sex is power.

BLOOM: This was a really hard transition to figure out ... the transitions into the music video are the hardest things.

MCKENNA: When I look at that clip what I see is our production designer and his team putting up thousands of hand-glued sequins to make that bridge in the back, those are all hand-glued.

BLOOM: And our amazing choreographer’s work. And this was the day that we after we shot “Sex With a Stranger,” which is me in six-inch stripper heels and someone was like, ‘You’re shooting two musical numbers back to back, are you okay?’ and I was like, ‘I’m fine.’ And I wasn’t fine. I had a lot of Advil.

2. The Sexy Getting-Ready Song

HUNT:  The next song appears in episode one, sung by Rebecca. If this could exist in real life, this would be a song comprised of people performing from Destiny’s Child and TLC. It’s of course “The Sexy Getting-Ready Song.” I don’t think there’s a woman in the room who can’t identify with this entirely painful process that you detail in the song.

BLOOM: It’s about the ideal of cool and femininity. In the pilot, we had the “West Covina” song reprise, but we needed another one. What we always do when we don’t know where to put a song or know what the next song should be, is ask: What are the emotional highs and lows of the episode? And Aline was like, “Well, she’s at her happiest when she’s getting ready for this party ...’

MCKENNA: Right, the anticipation of the party.

BLOOM: And you were like, could we do something where she’s getting ready? There is this feminine ideal of a woman and her powder puff, a woman and her towelette, very carefully putting on lipstick. But when I get ready for a party, it’s squalor, it’s horrifying. 

MCKENNA: One of the things I most remember from Reality Bites is when she’s got the Jolen Cream Bleach on her upper lip.

BLOOM: There were just so many cuts from the song. There was a whole thing where Rebecca puts duct tape over the Spanx because the Spanx weren’t enough.

MCKENNA: There’s a thing where you put the Spanx on, there’s still like a little roll of flab that goes over the Spanx and you don’t know what to do with it.

BLOOM: Oh no, well I have, when I put Spanx on, I still have like a round belly ... like, the Spanx don’t help that. 

HUNT: I just have to point out the look on Adam’s face while we’re discussing this. I don’t want to leave you out of the discussion, by the way.

SCHLESINGER I actually literally had nothing to do with this particular song, so it’s fine.

MCKENNA: Here’s the thing, we’ve done 49 pieces of music on the show, there are only two that Adam didn’t work on and this is one of them.

HUNT: Should we hear the demo for this?

MCKENNA: Please, if you wouldn’t mind.

MCKENNA: So one thing that was really interesting about this one was that Rachel sang the demo in this really over-sung way, and then when she went to produce the song with Jack Dolgen, who is other songwriter and who produced this track, she came back and then sang in a much more pure way. 

BLOOM: We didn’t want it to be joke on a joke. So I kind of recorded it more straight and then it wasn’t as fun. So we went back and recorded it the way I did in the demo ... with no articulation.

MCKENNA: Most of the people who work on the show are not music people, and so they can't express themselves in musical terms. I’m one of them and so I always say, ‘This is what a monkey would say …’ That’s my expression for when I give notes on music cause I don’t really know. You’ll see in the video the girl with the red curly hair who is next to Rachel is Beyoncé’s lead dancer.

BLOOM: She’s in "Single Ladies"! And so, I get there and she’s like ‘Hi! I’m Beyoncé’s best friend,’ and I’m just like ‘I ... I’m broke ... nice to meet you.’

MCKENNA: Alright, let’s watch it. 

BLOOM: The male crew had to avert their eyes for the whole scene ... the director couldn’t watch this. ‘What are you doing? Why are you turning your eye inside out?’ And I was like, ‘That’s how you make it look like you’re not wearing eyeliner but like you totally are ...” They learned a lot that day.

3. Gettin' Bi

HUNT: We are now to what I think might be the lost track [from] Huey Lewis and the News’ album Sports, it’s called “Gettin’ Bi,” sung by Darryl in episode 14. To see Darryl celebrating his identity … I don’t think we can underplay the significance of this storyline, too. I’ve never seen bisexuality represented in any multidimensional way, and in a way that’s funny but also very respectful. You’re telling so much, but also not downplaying what this process is for people. Maybe I’ll have Adam start? How did you land on this particular style for this song?

SCHLESINGER: There are a few steps whenever we’re trying to get a song going. First, it’s just coming up with what’s the song going to be and what’s the idea, and in a lot of cases Rachel already has that — sometimes she doesn’t but most of the time she has a vague thing or specific thing. In this case, these guys came and said they wanted to do a song about Darryl’s coming out as bisexual and Rachel had an idea for a song — I mean this is a typical thing too — I always start thinking about then what rock genre we can do and she starts thinking about what Broadway tune. So she said she wanted to do a song called “Bi the Bi …”

BLOOM: Oh, yeah! I remember that.

SCHLESINGER: And then I sort of pitched this idea of, what if it was sort of this Huey Lewis 80’s kind of thing. It seems like what he would like and would think was really cool. I really like Huey Lewis and I was looking for an excuse to do something. So anyway so they said, "Okay, give it a shot," and I went and did a demo.

MCKENNA: I had a very brief conversation with Adam on the phone and then I send him a list of preconceptions about bi people and we had talked to some representatives from GLAAD about some preconceptions about bi people, and then it was like, I don’t have any time to think about that anymore and really what saves us time is very often Adam will come back with a demo and it’s like — and then we play them in the writer’s room and it’s like yep, that’s exactly what we want. 

BLOOM: Yep, that’s done, that’s done.

MCKENNA: So let’s play the demo cause this was a hallelujah moment in the writer’s room.

BLOOM: We don’t want to sell out Darryl in this song. We don’t want to make the song sound creepy.

SCHLESINGER: Basically the extra joke in that scene is that no one in the office gives a shit. And they’re just like, Oh, God, we just don’t want to think about you having any kind of sex at all.

MCKENNA: “Please get him to stop, please.”

SCHLESINGER: He’s dancing around, he thinks this is the biggest news and they’re like, can we go now. I have work to do. 

MCKENNA: One of things is [actor] Pete [Gardner] had never sung before ever. He had never sung, so his wife told us that he breaks the songs down into very short pieces and sings them over and over again.

BLOOM: Same with the choreography. He’s so great. He’s unbelievable. He was Tina Fey’s improv coach in Chicago. Pete is a Second City Chicago guy. He’s a brilliant improviser. 

SCHLESINGER: My favorite trivia about Pete is that he’s from Scarsdale [like Bloom’s character]. I thought he was from, like, Tulsa. 

BLOOM: Oh my God!

SCHLESINGER: He always played this kind of Midwestern type of guy, but he’s from fucking Scarsdale. 

BLOOM: The other fun fact about Pete is he’s the greatest person who’s ever existed. He is the most gracious. I mean our whole cast is so wonderful but, like, Pete walks on the set with such a gracious heart. I think that Darryl and Rebecca are actually the most similar characters we have on the show because they’re both optimists with a deep sadness.

MCKENNA: They’re both very self-aware.

4. Heavy Boobs

HUNT: Next up is the anthem that I think a lot of us can relate to. It appears in episode 16: “Heavy Boobs.” The best.

MCKENNA: So this is an example of a time I said to Rachel, ‘Just play me any song that you have that we could use in the show. Anything we haven’t used.’

BLOOM: And when she says that, by the way, I have on my computer a list of every song idea I’ve ever had for the past six years that I’ve never used. “Heavy Boobs” is an idea that I’d had for a while and then we just got busy with the show. I think I had this idea right before we went into the pilot for the show. 

MCKENNA: And there was no story-related reason to do this at all. But as soon as she played it for me, I was like ‘That’s going in the show.’

BLOOM: And so I remember you were pitching me episode 16 and you were like, ‘This is where we can do “Heavy Boobs,”' and I was like what? How?

MCKENNA: I don’t have boobs of the big size and I’m fascinated with them.

BLOOM: Aline is always trying to get me to show more cleavage on the show.

HUNT: It reminds of Gwen Stefani’s “Wind It Up,” especially the talk-rap in the middle. Was that an inspiration?

BLOOM: So the main inspiration was I remember listening to the Diva album by Beyoncé a lot and the idea of doing this kind of a rap song is very Beyoncé.

SCHLESINGER: These are actually some of the harder ones to produce because the thing with contemporary pop tracks now is they’re all very unique and they don’t really sound like other contemporary songs. So I have to try to come up with a track that sounds like a legitimate track, like Beyoncé’s, which are the coolest tracks in the world. Something like “Settle for Me” is easier to execute because I basically do a piano demo and hand it off to a Broadway orchestrator and say, ‘Could you just make 40 people play this?’ So I worked on this track for a while, and Rachel and I both happened to be in New York during the week that we recorded this, and we actually did it at Jungle City, which is the studio where Beyoncé does her records. It was pretty cool.

MCKENNA: Let’s play the demo!

SCHLESINGER: So she’ll send me that and then I’ll actually chop up her iPhone vocal or whatever you did this on and, like, put it on a grid and build a beat against it and then send it back to her. And then she’ll come in and replace it with basically the same thing.

BLOOM: A lot of times I’m recording stuff a capella because I don’t have access to a piano, I have to record it on set and in my head. I hear it so well, the chords. It sounds like, oh yeah! But I’m only singing melody. So I remember you were like, what are the chords? And I was like, it’s not obvious? And it’s like, No, you fucking idiot, of course it’s not obvious.

SCHLESINGER: Well, sometimes it is, but something like that, it’s more just rhythmic.

BLOOM: Did I send you a chord breakdown ever? I think we got on the phone and I played a little.

MCKENNA: But I want to say, one of the things about the songs is that they are are not spoofy even though they’re comedy songs. What I think Adam in particular does so brilliantly with the production of them is that they send up the thing we’re talking about, but are still perfectly legit pop songs, with funny lyrics. 

BLOOM: The inspiration for this song it was obviously my boobs, but let’s get into why. For the longest time, after I went on birth control — it’s TMI but I don’t care. I go on birth control to regulate my periods and instantly my boobs swelled like — the Grinch’s heart in Whoville. And I grew. And half the month I would be in pain, I literally couldn’t run. And this was, like, for four years, and I went to gyno after gyno and they were like, ‘Cut down on your caffeine.’ I don’t drink coffee! And they were like, then, ‘Get more sleep.’ For a long time I would look in the mirror at my big boobs and be like, ‘I don’t know who this person is. This is not the way my body is naturally supposed to be.’ Finally I went to a doctor who was like oh, you’re on the wrong birth control. So, I know that boobs are a sexual …

MCKENNA: But they’re bags of fat. 

BLOOM: But they’re bags of fat! I view things through a feminist lens because the male gaze is very sexualized, right? So I really like to call these songs “boner-killer songs.” I like to imagine that if you tried to jerk off, you would lose your boner.

MCKENNA: I think some boners have made it through this one! I just want to point out that all the women in this are not wearing bras. 

BLOOM: Yep. I’m not either. 

HUNT: That’s very clear. 

SCHLESINGER: You know, we put these videos online separately from the show and then we always talk about which ones are doing well. Aline called me up and was like, “Heavy Boobs” is doing great! and I’m like, ‘It’s called “Heavy Boobs.”’ This just in!

BLOOM: When I was originally writing the song, I think the first thing that came into the song was the bridge. Here is a list of all the objects I can put under my boobs. I was writing it in the office and so I actually did this. I took off my shirt and I started going around the office and just picking things up. That’s why all the things are things you could find in an office. [Laughter.] I really did stick a stapler, ten pencils, and there was a paperback copy of Catcher in the Rye, but we couldn’t clear using the title Catcher in the Rye [Laughter.] Literally, like, and then my dog’s dog bone I think I did that, remote control, I literally can actually fit all these, and it’s under the boobs. I could very easily fit these under my boobs.

HUNT: How sore were you after that dance?

BLOOM: I was pretty sore. I bought all the dancers massages, I felt really bad.

5. Where's the Bathroom?

HUNT: Our final song is from episode eight, sung by Mrs. Bunch when she visits Rebecca. It’s called Where’s the Bathroom?

BLOOM: So, in the beginning there were Jews. [Laughter.] How do I begin with this one?

MCKENNA: Rebecca’s mother appears, you only hear her in the pilot and then you see kind of the side of her face and then here we were introducing her character and Rachel — this is the only time we introduce a character with, in full song.

BLOOM: The emotion of the piece is this looming figure — Rebecca’s mother — finally enters, and also in my head I was like how do we get [actress] Tovah Feldshuh an Emmy? [Laughter.] The idea of a mother coming in and immediately demolishing her daughter in song, and basically the definitive Jewish mother song that is true and specific to what Jewish mothers are.

SCHLESINGER: So basically Rachel had this long stream-of-consciousness stuff, which is most of the lyrics of this song; what we didn’t really have was a chorus.

MCKENNA: But having you guys work together is perfect because there is always one of you saying, ‘Ahh, this could be better, this could be better.’

SCHLESINGER: We raise each other’s game that way, I think. This song was obviously a great idea, it was going to be fun, but we needed a great hook. Then Rachel threw out “Where’s the bathroom?” She needs to pee. And that’s the thing: She can’t go out because she needs to pee. And so there’s this extra tension because she needs to pee.

HUNT: It’s a long way from the airport. West Covina is a very long way. Let’s hear the demo?

BLOOM: Well, as you see that is sort of speaky-sung. I knew that Adam would have a way better melody.

SCHLESINGER: When the show is over I’m actually just going to get a gig playing at Sammy’s Romanian Steakhouse. [Laughter.]

MCKENNA: That’s one of the absolute best demos — did we make it available on iTunes or did you refuse?

SCHLESINGER: I sure hope we didn’t. [Laughter.]

HUNT: The orchestration that goes with the song has these wonderful shades of Fiddler of the Roof, too. Let’s see the final video version?

BLOOM: This really is one of the only songs I think we’ve done where every line is a different thought and a different motivation. For Tovah, in all her scripts, everything is meticulously mapped out. It’s a song where you have to be just a good fucking actor. She’s totally brilliant.